(S)-α-methyl-N-(2-methylcyclopentylidene)benzenemethanamide | 193468-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-α-methyl-N-(2-methylcyclopentylidene)benzenemethanamide
• CAS: 193468-10-9
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: NFDJAHOLOJYMLM-YJHWBCAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-α-methyl-N-(2-methylcyclopentylidene)benzenemethanamide 在 2,6-二甲基吡啶 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 生成 (3aR,6aR)-3a-Methyl-1-((S)-1-phenyl-ethyl)-octahydro-cyclopenta[b]pyrrole
  参考文献：
  名称：

  Enantioselective Access to Five- and Six-membered Nitrogen-containing Heterocycles, Based on the Asymmetric Michael Addition of Chiral Imines and Chiral Enamino Esters

  摘要：

  The addition reaction of chiral imines, (ent-10, 48, 70) and chiral enamino esters (52, 55, 73) with maleic anhydride (32), citraconic anhydride (57), alpha-chloroacrylonitrile (29), and nitroethylene (74), has been investigated. These condensations proved to be in general highly regio-, diastereo-, and enantioselective. In most cases the primary adducts underwent an in situ N-heterocyclization, allowing the enantioselective access to nitrogen-containing, five- and six-membered heterocycles.

  DOI：

  10.3987/com-97-s(n)47
• 作为产物：
  描述：

  2-甲基环戊酮 、 (S)-(-)- α-甲基苄胺 生成 (S)-α-methyl-N-(2-methylcyclopentylidene)benzenemethanamide
  参考文献：
  名称：

  不对称顺序迈克尔加成–涉及手性亚胺的N-杂环化反应

  摘要：

  手性亚胺的反应ENT - 14，27，和31与α氯代6，马来酸酐9，和柠康酸酐35进行了研究。在NaBH 3 CN-还原粗产物之后，将亚胺27加到6中提供了作为单一异构体的双环衍生物28。当相同的方案应用于亚胺ENT - 14，加合物的混合物29和30获得。将亚胺31加至6得到环状吡咯32.亚胺27与马来酸酐9的缩合得到化合物33，为单一异构体。将亚胺ent - 14添加到柠康酸酐35中，将粗产物与CH 2 N 2酯化后，导致形成加合物36和37的混合物。在区域和环氧基的基础上讨论了这些氮杂环化的机理观察到立体选择性。

  DOI：

  10.1002/ijch.199700010

文献信息

• Enantioselective Synthesis of Homologous Methyl-Substituted Bicyclic Enones Through Michael-Type Alkylation of Chiral Imines
  作者：Virginie Goubaud、Robert Azerad

  DOI：10.1080/00397919608003696

  日期：1996.3

  Abstract The preparation of 4a-methyl-substituted bicyclic enones in high enantiomeric purity is described, involving a Michael alkylation of (R)- or (S)-1-phenylethyl imines of the corresponding (±)-2-methylcyclopentanone, 2-methyl-cyclohexanone, 2-methylcycloheptanone, and 2-methylcyclooctanone with methyl vinyl ketone.

  摘要 描述了高对映体纯度的 4a-甲基取代的双环烯酮的制备，包括相应的 (±)-2-甲基环戊酮、2-甲基环戊酮的 (R)- 或 (S)-1-苯乙基亚胺的迈克尔烷基化-环己酮、2-甲基环庚酮和2-甲基环辛酮与甲基乙烯基酮。
• Condensation of chiral imines and chiral β-enaminoesters with maleic and citraconic anhydrides
  作者：Christian Cavé、Abdoulaye Gassama、Jacqueline Mahuteau、Jean d'Angelo、Claude Riche

  DOI：10.1016/s0040-4039(97)01046-0

  日期：1997.7

  Condensations of chiral imines 1 and 4, and chiral enaminoesters 10 and 13, with maleic and citraconic anhydrides were reported. These experimental outcomes can be rationalized by invoking the compact, endo-approaches of the two reactants 18.

  据报道手性亚胺1和4，手性烯氨基酯10和13与马来酸酐和柠康酸酐的缩合。这些实验结果可以通过调用两种反应物18的紧凑，内部方法来合理化。
• Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones
  作者：V Morisson、J.P Barnier、L Blanco

  DOI：10.1016/s0040-4020(98)00411-6

  日期：1998.7

  Optically active alpha-methyl alpha-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme(R)-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters
  作者：Cyrille Thominiaux、Sébastien Roussé、Didier Desmaële、Jean d'Angelo、Claude Riche

  DOI：10.1016/s0957-4166(99)00180-9

  日期：1999.5

  Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)-pentalenone through a Nef reaction. Condensation of the enamino ester derived from 2-carbethoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael adduct. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Desmaele, Didier; Cave, Christian; Dumas, Francoise, Enantiomer, 2001, vol. 6, # 5, p. 289 - 298
  作者：Desmaele, Didier、Cave, Christian、Dumas, Francoise、d'Angelo, Jean

  DOI：——

  日期：——