(-)-N-(1,2,3,4-tetrahydronaphthalen-2-yl)-propionamide | 100608-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (-)-N-(1,2,3,4-tetrahydronaphthalen-2-yl)-propionamide
• 英文别名: N-(1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
• CAS: 100608-70-6
• 化学式: C₁₃H₁₇NO
• mdl: MFCD21366075
• 分子量: 203.284
• InChiKey: PGUPSDWJGZRTBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  β-四氢萘酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 [NH2Et2][{(S)-BinapRuCl}2(μ-Cl)3] 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、10.0 MPa 条件下， 反应 40.0h， 生成 (-)-N-(1,2,3,4-tetrahydronaphthalen-2-yl)-propionamide
  参考文献：
  名称：

  钌催化的由2-Tetralone和3-Chromanone衍生的三取代酰胺的对映选择性加氢：取代对酰胺臂和芳环的影响

  摘要：

  在酸性条件下，由四氢萘酮和苯并二氢吡喃酮衍生物和伯酰胺一步制备环状酰胺。这些带有内环三取代碳-碳双键的酰胺的对映选择性氢化是在室温下在钌催化剂的存在下进行的。一方面，当使用单核预催化剂时，酰胺基的性质对氢化的对映选择性几乎没有影响。另一方面，在四氢萘酮和苯并二氢吡喃酮骨架上某些特定位置的配位原子的存在导致对映体过量的急剧减少。

  DOI：

  10.1002/adsc.200390017

文献信息

• [EN] ARYLSULFONYLMETHYL OR ARYLSULFONAMIDE SUBSTITUTED AROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MADULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSES AROMATIQUES D'ARYLSULFONYLMETHYLE OU D'ARYLSULFONAMIDE SUBSTITUES PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040178A1

  公开（公告）日：2006-04-20

  The present invention relates to aromatic compounds of the formula (I), wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry 1 or 2 radicals Rb; X is N or CH; Y is O, S, -CH=N-, -CH=CH- or -N=CH-; A is CH2i O or S; E is CR6R7 or NR 3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-C4-­alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4­-alkenyl, formyl or C,-C3-alkylcarbonyl; R1a is H, C2-C4-alkyl, C3-C4-cycloalkyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3-C4 -cycloalkyl, or R1a and R2 together are (CH2)n with n being 2 or 3, or R1a and R2a together are (CH2)n with n being 2 or 3; R2 and R2a are independently of each other H, CH3, CH2F, CHF2 or CF3; R3 is H or C1-C4-alkyl; R6, R7 independently of each other are selected from H, C1-C2-alkyl and fluorinated C1-C2-alkyl; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及式(I)的芳香族化合物，其中Ar是苯基或芳香族5-或6-成员C-键合杂芳基，其中Ar可以携带1个基团Ra，Ar也可以携带1个或2个基团Rb；X是N或CH；Y是O、S、-CH=N-、-CH=CH-或-N=CH-；A是CH2i、O或S；E是CR6R7或NR3；R1是C1-C4-烷基、C3-C4-环烷基、C3-C4-环烷基甲基、C3-C4-烯基、氟代C1-C4-烷基、氟代C3-C4-环烷基、氟代C3-C4-环烷基甲基、氟代C3-C4-烯基、甲酰基或C,-C3-烷基羰基；R1a是H、C2-C4-烷基、C3-C4-环烷基、C3-C4-烯基、氟代C1-C4-烷基、氟代C3-C4-环烷基，或R1a和R2一起是(CH2)n，其中n为2或3，或R1a和R2a一起是(CH2)n，其中n为2或3；R2和R2a彼此独立地是H、CH3、CH2F、CHF2或CF3；R3是H或C1-C4-烷基；R6、R7彼此独立地选自H、C1-C2-烷基和氟代C1-C2-烷基；以及其生理耐受的酸盐。该发明还涉及使用式I的化合物或其药学上可接受的盐制备用于治疗对多巴胺D3受体配体敏感的医疗疾病的药物组合物。
• Ruthenium-Catalysed Enantioselective Hydrogenation of Trisubstituted Enamides Derived from 2-Tetralone and 3-Chromanone: Influence of Substitution on the Amide Arm and the Aromatic Ring
  作者：J. L. Renaud、P. Dupau、A.-E. Hay、M. Guingouain、P. H. Dixneuf、C. Bruneau

  DOI：10.1002/adsc.200390017

  日期：2003.1

  Cyclic enamides were prepared in one step from tetralone and chromanone derivatives and primary amides under acidic conditions. The enantioselective hydrogenation of these enamides bearing an endocyclic trisubstituted carbon-carbon double bond was performed at room temperature in the presence of ruthenium catalysts. On the one hand, the nature of the amide group had little influence on the enantioselectivity

  在酸性条件下，由四氢萘酮和苯并二氢吡喃酮衍生物和伯酰胺一步制备环状酰胺。这些带有内环三取代碳-碳双键的酰胺的对映选择性氢化是在室温下在钌催化剂的存在下进行的。一方面，当使用单核预催化剂时，酰胺基的性质对氢化的对映选择性几乎没有影响。另一方面，在四氢萘酮和苯并二氢吡喃酮骨架上某些特定位置的配位原子的存在导致对映体过量的急剧减少。
• Processes for the Preparation of Rotigotine and Intermediates Thereof
  申请人：Apotex Inc.

  公开号：US20170305877A1

  公开（公告）日：2017-10-26

  The present invention provides processes for the preparation of a compound of Formula 2 or a salt thereof, wherein R 1 is selected from the group consisting of H, C 1 -C 3 alkyl, and C(0)R 3 ; R 3 is selected from the group consisting of C 1 -C 6 alkyl, C 6 -C 10 aryl and C 7 -C 20 arylalkyl; the carbon atom marked with “*” is racemic, enantiomerically enriched in the (R)-configuration, or enantiomerically enriched in the (S)-configuration. Also provided are intermediate compounds of the processes.

  本发明提供了制备式2化合物或其盐的方法，其中R1选自H、C1-C3烷基和C(0)R3，R3选自C1-C6烷基、C6-C10芳基和C7-C20芳基烷基；标有“*”的碳原子是外消旋的，富集(R)-构型的对映体或富集(S)-构型的对映体。同时提供了所述方法的中间体化合物。
• Substituted 2-amidotetralins as melatonin agonists and antagonists
  申请人：Northwestern University

  公开号：US05151446A1

  公开（公告）日：1992-09-29

  The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as therapeutic and diagnostic reagents.

  本发明涉及具有褪黑激素受体活性的化合物，特别是取代的2-氨基四氢萘衍生物；包括含有这种化合物的药物制剂；以及使用这些化合物作为治疗和诊断试剂的方法。
• Arylsulfonylmethyl or arylsulfonamide substituted aromatic compounds suitable for treating disorders that respond to modulation of the Dopamine D3 receptor
  申请人：Drescher Karla

  公开号：US20090012074A1

  公开（公告）日：2009-01-08

  The present invention relates to aromatic compounds of the formula I wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical R a and wherein Ar may also carry 1 or 2 radicals R b ; X is N or CH; Y is O, S, —CH═N—, —CH═CH— or —N═CH—; A is CH 2 , O or S; E is CR 6 R 7 or NR 3 ; R 1 is C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, C 3 -C 4 -cycloalkylmethyl, C 3 -C 4 -alkenyl, fluorinated C 1 -C 4 -alkyl, fluorinated C 3 -C 4 -cycloalkyl, fluorinated C 3 -C 4 -cycloalkylmethyl, fluorinated C 3 -C 4 -alkenyl, formyl or C 1 -C 3 -alkylcarbonyl; R 1a is H, C 2 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, C 3 -C 4 -alkenyl, fluorinated C 1 -C 4 -alkyl, fluorinated C 3 -C 4 -cycloalkyl, or R 1a and R 2 together are (CH 2 ) n with n being 2 or 3, or R 1a and R 2a together are (CH 2 ) n with n being 2 or 3; R 2 and R 2a are independently of each other H, CH 3 , CH 2 F, CHF 2 or CF 3 ; R 3 is H or C 1 -C 4 -alkyl; R 6 , R 7 independently of each other are selected from H, C 1 -C 2 -alkyl and fluorinated C 1 -C 2 -alkyl; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及公式I的芳香族化合物，其中Ar是苯基或含有5或6个成员的芳香族C-连接杂环基团，其中Ar可以携带1个基团Ra，也可以携带1或2个基团Rb；X是N或CH；Y是O，S，-CH═N-，-CH═CH-或-N═CH-；A是CH2，O或S；E是CR6R7或NR3；R1是C1-C4烷基，C3-C4环烷基，C3-C4环烷基甲基，C3-C4烯基，氟代C1-C4烷基，氟代C3-C4环烷基，氟代C3-C4环烷基甲基，氟代C3-C4烯基，甲酰基或C1-C3烷基羰基；R1a是H，C2-C4烷基，C3-C4环烷基，C3-C4烯基，氟代C1-C4烷基，氟代C3-C4环烷基，或R1a和R2一起是(CH2)n，其中n为2或3，或R1a和R2a一起是(CH2)n，其中n为2或3；R2和R2a相互独立地是H，CH3，CH2F，CHF2或CF3；R3是H或C1-C4烷基；R6，R7相互独立地选择自H，C1-C2烷基和氟代C1-C2烷基；以及其生理耐受酸盐。本发明还涉及使用公式I的化合物或其药学上可接受的盐制备用于治疗可通过多巴胺D3受体配体治疗的医疗障碍的制药组合物的用途。