Synthesis of adamantyl-containing phenylpiperidines View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2015-10

AUTHORS

Vera A. Shadrikova, Evgeny V. Golovin, Vadim A. Shiryaev, Marat R. Baimuratov, Victor B. Rybakov, Yuri N. Klimochkin

ABSTRACT

The reduction of quaternary 1-(adamantan-1-yl)pyridinium salts with sodium borohydride in ethanol gave 1-(adamantan-1-yl)-1,2,3,6-tetrahydropyridines that reacted with benzene in trifluoromethanesulfonic acid medium, leading to the formation of 1-(adamantan-1-yl)-phenylpiperidines with various spatial orientation of the phenyl substituent. The structure of the obtained phenylpiperidines was confirmed by the spectral dataset. The thermodynamic stability calculations for the conformers of phenylpiperidines were performed with the B3LYP/6-311++(d,p) method. More... »

PAGES

891-898

References to SciGraph publications

  • 2014-03. Adamantylation of saturated nitrogen-containing heterocycles in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2006-01-20. Paradigm shift in neuroprotection by NMDA receptor blockade: Memantine and beyond in NATURE REVIEWS DRUG DISCOVERY
  • 1992-07. Antiviral activity of adamantane series hydroxy derivatives in PHARMACEUTICAL CHEMISTRY JOURNAL
  • 2015-01-06. Adamantylation of Pyridine Derivatives in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s10593-015-1792-4

    DOI

    http://dx.doi.org/10.1007/s10593-015-1792-4

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1024652134


    Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
    Incoming Citations Browse incoming citations for this publication using opencitations.net

    JSON-LD is the canonical representation for SciGraph data.

    TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

    [
      {
        "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
        "about": [
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Chemical Sciences", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0305", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Organic Chemistry", 
            "type": "DefinedTerm"
          }
        ], 
        "author": [
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Shadrikova", 
            "givenName": "Vera A.", 
            "id": "sg:person.015226001707.75", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015226001707.75"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Golovin", 
            "givenName": "Evgeny V.", 
            "id": "sg:person.016620742707.68", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016620742707.68"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Shiryaev", 
            "givenName": "Vadim A.", 
            "id": "sg:person.07505043652.30", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07505043652.30"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Baimuratov", 
            "givenName": "Marat R.", 
            "id": "sg:person.011031671452.57", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.011031671452.57"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, 119991, Moscow, Russia", 
              "id": "http://www.grid.ac/institutes/grid.14476.30", 
              "name": [
                "Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, 119991, Moscow, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Rybakov", 
            "givenName": "Victor B.", 
            "id": "sg:person.0643361531.23", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.0643361531.23"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Klimochkin", 
            "givenName": "Yuri N.", 
            "id": "sg:person.07436126201.08", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07436126201.08"
            ], 
            "type": "Person"
          }
        ], 
        "citation": [
          {
            "id": "sg:pub.10.1038/nrd1958", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1053003644", 
              "https://doi.org/10.1038/nrd1958"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s10593-014-1628-7", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1021144321", 
              "https://doi.org/10.1007/s10593-014-1628-7"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/bf00777145", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1008098105", 
              "https://doi.org/10.1007/bf00777145"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1134/s1070428014030270", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1052115250", 
              "https://doi.org/10.1134/s1070428014030270"
            ], 
            "type": "CreativeWork"
          }
        ], 
        "datePublished": "2015-10", 
        "datePublishedReg": "2015-10-01", 
        "description": "The reduction of quaternary 1-(adamantan-1-yl)pyridinium salts with sodium borohydride in ethanol gave 1-(adamantan-1-yl)-1,2,3,6-tetrahydropyridines that reacted with benzene in trifluoromethanesulfonic acid medium, leading to the formation of 1-(adamantan-1-yl)-phenylpiperidines with various spatial orientation of the phenyl substituent. The structure of the obtained phenylpiperidines was confirmed by the spectral dataset. The thermodynamic stability calculations for the conformers of phenylpiperidines were performed with the B3LYP/6-311++(d,p) method.", 
        "genre": "article", 
        "id": "sg:pub.10.1007/s10593-015-1792-4", 
        "inLanguage": "en", 
        "isAccessibleForFree": false, 
        "isPartOf": [
          {
            "id": "sg:journal.1429545", 
            "issn": [
              "0132-6244", 
              "1573-8353"
            ], 
            "name": "Chemistry of Heterocyclic Compounds", 
            "publisher": "Springer Nature", 
            "type": "Periodical"
          }, 
          {
            "issueNumber": "10", 
            "type": "PublicationIssue"
          }, 
          {
            "type": "PublicationVolume", 
            "volumeNumber": "51"
          }
        ], 
        "keywords": [
          "stability calculations", 
          "thermodynamic stability calculations", 
          "sodium borohydride", 
          "acid medium", 
          "spectral datasets", 
          "spatial orientation", 
          "borohydride", 
          "structure", 
          "calculations", 
          "orientation", 
          "method", 
          "reduction", 
          "ethanol", 
          "formation", 
          "salt", 
          "benzene", 
          "medium", 
          "synthesis", 
          "dataset", 
          "phenyl substituents", 
          "quaternary 1", 
          "phenylpiperidine", 
          "B3LYP/6", 
          "substituents", 
          "conformers", 
          "tetrahydropyridine"
        ], 
        "name": "Synthesis of adamantyl-containing phenylpiperidines", 
        "pagination": "891-898", 
        "productId": [
          {
            "name": "dimensions_id", 
            "type": "PropertyValue", 
            "value": [
              "pub.1024652134"
            ]
          }, 
          {
            "name": "doi", 
            "type": "PropertyValue", 
            "value": [
              "10.1007/s10593-015-1792-4"
            ]
          }
        ], 
        "sameAs": [
          "https://doi.org/10.1007/s10593-015-1792-4", 
          "https://app.dimensions.ai/details/publication/pub.1024652134"
        ], 
        "sdDataset": "articles", 
        "sdDatePublished": "2022-06-01T22:13", 
        "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
        "sdPublisher": {
          "name": "Springer Nature - SN SciGraph project", 
          "type": "Organization"
        }, 
        "sdSource": "s3://com-springernature-scigraph/baseset/20220601/entities/gbq_results/article/article_651.jsonl", 
        "type": "ScholarlyArticle", 
        "url": "https://doi.org/10.1007/s10593-015-1792-4"
      }
    ]
     

    Download the RDF metadata as:  json-ld nt turtle xml License info

    HOW TO GET THIS DATA PROGRAMMATICALLY:

    JSON-LD is a popular format for linked data which is fully compatible with JSON.

    curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/s10593-015-1792-4'

    N-Triples is a line-based linked data format ideal for batch operations.

    curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/s10593-015-1792-4'

    Turtle is a human-readable linked data format.

    curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s10593-015-1792-4'

    RDF/XML is a standard XML format for linked data.

    curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s10593-015-1792-4'


     

    This table displays all metadata directly associated to this object as RDF triples.

    138 TRIPLES      22 PREDICATES      56 URIs      44 LITERALS      6 BLANK NODES

    Subject Predicate Object
    1 sg:pub.10.1007/s10593-015-1792-4 schema:about anzsrc-for:03
    2 anzsrc-for:0305
    3 schema:author N837a6908d65447379d70d31f68b0fee4
    4 schema:citation sg:pub.10.1007/bf00777145
    5 sg:pub.10.1007/s10593-014-1628-7
    6 sg:pub.10.1038/nrd1958
    7 sg:pub.10.1134/s1070428014030270
    8 schema:datePublished 2015-10
    9 schema:datePublishedReg 2015-10-01
    10 schema:description The reduction of quaternary 1-(adamantan-1-yl)pyridinium salts with sodium borohydride in ethanol gave 1-(adamantan-1-yl)-1,2,3,6-tetrahydropyridines that reacted with benzene in trifluoromethanesulfonic acid medium, leading to the formation of 1-(adamantan-1-yl)-phenylpiperidines with various spatial orientation of the phenyl substituent. The structure of the obtained phenylpiperidines was confirmed by the spectral dataset. The thermodynamic stability calculations for the conformers of phenylpiperidines were performed with the B3LYP/6-311++(d,p) method.
    11 schema:genre article
    12 schema:inLanguage en
    13 schema:isAccessibleForFree false
    14 schema:isPartOf N116bd0c81c164b289f743786f73d04a6
    15 Na524def5dcc242dcbfde8420289b7cd9
    16 sg:journal.1429545
    17 schema:keywords B3LYP/6
    18 acid medium
    19 benzene
    20 borohydride
    21 calculations
    22 conformers
    23 dataset
    24 ethanol
    25 formation
    26 medium
    27 method
    28 orientation
    29 phenyl substituents
    30 phenylpiperidine
    31 quaternary 1
    32 reduction
    33 salt
    34 sodium borohydride
    35 spatial orientation
    36 spectral datasets
    37 stability calculations
    38 structure
    39 substituents
    40 synthesis
    41 tetrahydropyridine
    42 thermodynamic stability calculations
    43 schema:name Synthesis of adamantyl-containing phenylpiperidines
    44 schema:pagination 891-898
    45 schema:productId N278c3f7098bf4998b290825f1c422ecd
    46 N2f11e140f02540fbb0eee6d8c6661337
    47 schema:sameAs https://app.dimensions.ai/details/publication/pub.1024652134
    48 https://doi.org/10.1007/s10593-015-1792-4
    49 schema:sdDatePublished 2022-06-01T22:13
    50 schema:sdLicense https://scigraph.springernature.com/explorer/license/
    51 schema:sdPublisher N86a7e1f885434ef48ba67aa76af5d831
    52 schema:url https://doi.org/10.1007/s10593-015-1792-4
    53 sgo:license sg:explorer/license/
    54 sgo:sdDataset articles
    55 rdf:type schema:ScholarlyArticle
    56 N116bd0c81c164b289f743786f73d04a6 schema:volumeNumber 51
    57 rdf:type schema:PublicationVolume
    58 N278c3f7098bf4998b290825f1c422ecd schema:name dimensions_id
    59 schema:value pub.1024652134
    60 rdf:type schema:PropertyValue
    61 N2f11e140f02540fbb0eee6d8c6661337 schema:name doi
    62 schema:value 10.1007/s10593-015-1792-4
    63 rdf:type schema:PropertyValue
    64 N632f0f0b9784417d9015f874f79cf564 rdf:first sg:person.07436126201.08
    65 rdf:rest rdf:nil
    66 N7d22482742b7401f8cb4e17e8a315572 rdf:first sg:person.0643361531.23
    67 rdf:rest N632f0f0b9784417d9015f874f79cf564
    68 N837a6908d65447379d70d31f68b0fee4 rdf:first sg:person.015226001707.75
    69 rdf:rest Nf5185a6bf93f465eb4f072895c46f5a1
    70 N86a7e1f885434ef48ba67aa76af5d831 schema:name Springer Nature - SN SciGraph project
    71 rdf:type schema:Organization
    72 N895aa298446d4da5a6e403db38242632 rdf:first sg:person.07505043652.30
    73 rdf:rest Nfdaf6575e8924a53b1269da77dcd4b7c
    74 Na524def5dcc242dcbfde8420289b7cd9 schema:issueNumber 10
    75 rdf:type schema:PublicationIssue
    76 Nf5185a6bf93f465eb4f072895c46f5a1 rdf:first sg:person.016620742707.68
    77 rdf:rest N895aa298446d4da5a6e403db38242632
    78 Nfdaf6575e8924a53b1269da77dcd4b7c rdf:first sg:person.011031671452.57
    79 rdf:rest N7d22482742b7401f8cb4e17e8a315572
    80 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
    81 schema:name Chemical Sciences
    82 rdf:type schema:DefinedTerm
    83 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
    84 schema:name Organic Chemistry
    85 rdf:type schema:DefinedTerm
    86 sg:journal.1429545 schema:issn 0132-6244
    87 1573-8353
    88 schema:name Chemistry of Heterocyclic Compounds
    89 schema:publisher Springer Nature
    90 rdf:type schema:Periodical
    91 sg:person.011031671452.57 schema:affiliation grid-institutes:grid.445792.9
    92 schema:familyName Baimuratov
    93 schema:givenName Marat R.
    94 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.011031671452.57
    95 rdf:type schema:Person
    96 sg:person.015226001707.75 schema:affiliation grid-institutes:grid.445792.9
    97 schema:familyName Shadrikova
    98 schema:givenName Vera A.
    99 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015226001707.75
    100 rdf:type schema:Person
    101 sg:person.016620742707.68 schema:affiliation grid-institutes:grid.445792.9
    102 schema:familyName Golovin
    103 schema:givenName Evgeny V.
    104 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016620742707.68
    105 rdf:type schema:Person
    106 sg:person.0643361531.23 schema:affiliation grid-institutes:grid.14476.30
    107 schema:familyName Rybakov
    108 schema:givenName Victor B.
    109 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.0643361531.23
    110 rdf:type schema:Person
    111 sg:person.07436126201.08 schema:affiliation grid-institutes:grid.445792.9
    112 schema:familyName Klimochkin
    113 schema:givenName Yuri N.
    114 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07436126201.08
    115 rdf:type schema:Person
    116 sg:person.07505043652.30 schema:affiliation grid-institutes:grid.445792.9
    117 schema:familyName Shiryaev
    118 schema:givenName Vadim A.
    119 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07505043652.30
    120 rdf:type schema:Person
    121 sg:pub.10.1007/bf00777145 schema:sameAs https://app.dimensions.ai/details/publication/pub.1008098105
    122 https://doi.org/10.1007/bf00777145
    123 rdf:type schema:CreativeWork
    124 sg:pub.10.1007/s10593-014-1628-7 schema:sameAs https://app.dimensions.ai/details/publication/pub.1021144321
    125 https://doi.org/10.1007/s10593-014-1628-7
    126 rdf:type schema:CreativeWork
    127 sg:pub.10.1038/nrd1958 schema:sameAs https://app.dimensions.ai/details/publication/pub.1053003644
    128 https://doi.org/10.1038/nrd1958
    129 rdf:type schema:CreativeWork
    130 sg:pub.10.1134/s1070428014030270 schema:sameAs https://app.dimensions.ai/details/publication/pub.1052115250
    131 https://doi.org/10.1134/s1070428014030270
    132 rdf:type schema:CreativeWork
    133 grid-institutes:grid.14476.30 schema:alternateName Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, 119991, Moscow, Russia
    134 schema:name Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, 119991, Moscow, Russia
    135 rdf:type schema:Organization
    136 grid-institutes:grid.445792.9 schema:alternateName Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia
    137 schema:name Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia
    138 rdf:type schema:Organization
     




    Preview window. Press ESC to close (or click here)


    ...