(S)-4-cyclohexylpyrrolidin-2-one | 210585-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-4-cyclohexylpyrrolidin-2-one
• 英文别名: (4S)-4-cyclohexylpyrrolidin-2-one
• CAS: 210585-83-4
• 化学式: C₁₀H₁₇NO
• mdl: MFCD21691531
• 分子量: 167.251
• InChiKey: PWSUQCRPENFXDF-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-4-cyclohexylpyrrolidin-2-one 在 4-二甲氨基吡啶 、 双氧水 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 (S)-4-Cyclohexyl-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Steric and Electronic Influences on the Diastereoselectivity of the Rh₂(OAc)₄-Catalyzed C−H Insertion in Chiral Ester Diazoanilides:  Synthesis of Chiral, Nonracemic 4-Substituted 2-Pyrrolidinones

  摘要：

  A series of N-substituted N-(4-methoxyphenyl)-alpha-(alkoxycarbonyl)-alpha-diazoacetanilides, 10 and ent-10, wherein the alkoxy unit is a chiral auxiliary group [(-)-7 or (+)-8)], was prepared. The Rh-2(OAc)(4)-catalyzed intramolecular C-H insertion reaction of 10 and ent-10, under optimized reaction conditions, was investigated as a route for the preparation of chiral, nonracemic 4-substituted 2-pyrrolidinones. The cyclization reaction led only to 2-pyrrolidinone and 2-azetidinone products; the former products were obtained as major and, in a few cases, as exclusive products. The type and nature of the N-substituent in 10 or ent-10 was found to govern the diastereoselectivity of the reaction. With N-alkyl groups, steric effects play an important role in determining the diastereoselectivity of the reaction. However, with N-arylethyl substituents, electronic effects transmitted by the aryl substituents influenced the diastereoselectivity of the C-H insertion reaction. Specifically, electron-donating substituents were found to markedly attenuate the diastereoselectivity of the reaction. The diastereoselectivity of the reaction ranged from moderate to high (37-98%). A transition-state model to explain the observed diastereoselectivity is provided. The synthetic utility of the method is demonstrated by the stereoselective synthesis of the medicinally important, unnatural amino acid trans-4-cyclohexyl-L-proline 23.

  DOI：

  10.1021/jo971540q
• 作为产物：
  描述：

  (S)-(+)-4-cyclohexyl-1-(4-methoxyphenyl)-2-pyrrolidinone 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (S)-4-cyclohexylpyrrolidin-2-one
  参考文献：
  名称：

  Steric and Electronic Influences on the Diastereoselectivity of the Rh₂(OAc)₄-Catalyzed C−H Insertion in Chiral Ester Diazoanilides:  Synthesis of Chiral, Nonracemic 4-Substituted 2-Pyrrolidinones

  摘要：

  A series of N-substituted N-(4-methoxyphenyl)-alpha-(alkoxycarbonyl)-alpha-diazoacetanilides, 10 and ent-10, wherein the alkoxy unit is a chiral auxiliary group [(-)-7 or (+)-8)], was prepared. The Rh-2(OAc)(4)-catalyzed intramolecular C-H insertion reaction of 10 and ent-10, under optimized reaction conditions, was investigated as a route for the preparation of chiral, nonracemic 4-substituted 2-pyrrolidinones. The cyclization reaction led only to 2-pyrrolidinone and 2-azetidinone products; the former products were obtained as major and, in a few cases, as exclusive products. The type and nature of the N-substituent in 10 or ent-10 was found to govern the diastereoselectivity of the reaction. With N-alkyl groups, steric effects play an important role in determining the diastereoselectivity of the reaction. However, with N-arylethyl substituents, electronic effects transmitted by the aryl substituents influenced the diastereoselectivity of the C-H insertion reaction. Specifically, electron-donating substituents were found to markedly attenuate the diastereoselectivity of the reaction. The diastereoselectivity of the reaction ranged from moderate to high (37-98%). A transition-state model to explain the observed diastereoselectivity is provided. The synthetic utility of the method is demonstrated by the stereoselective synthesis of the medicinally important, unnatural amino acid trans-4-cyclohexyl-L-proline 23.

  DOI：

  10.1021/jo971540q

文献信息

• Multisite Organic-Inorganic Hybrid Catalysts for the Direct Sustainable Synthesis of GABAergic Drugs
  作者：Antonio Leyva-Pérez、Pilar García-García、Avelino Corma

  DOI：10.1002/anie.201403049

  日期：2014.8.11

  Multisite organic–inorganic hybrid catalysts have been prepared and applied in a new general, practical, and sustainable synthetic procedure toward industrially relevant GABA derivatives. The domino sequence is composed of seven chemical transformations which are performed in two one‐pot reactions. The method produces both enantiomeric forms of the product in high enantiopurity as well as the racemate

  已经制备了多位有机-无机杂化催化剂，并将其用于工业相关的GABA衍生物的新的通用，实用和可持续的合成程序中。多米诺骨牌序列由七个化学转化组成，这些转化在两个单罐反应中进行。该方法在单个柱纯化步骤后既以高对映体纯度生产产物的对映体形式，又以高收率生产外消旋体。该协议重点介绍了主要的工艺强化，催化剂可回收性和低废物产生的问题。