(cis)-1-benzyl-4-isobutyl-pyrrolidine-3-carboxylic acid ethyl ester | 261896-41-7

• 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: (cis)-1-benzyl-4-isobutyl-pyrrolidine-3-carboxylic acid ethyl ester
• 英文别名: rel-Ethyl (3R,4S)-4-(2-methylpropyl)-1-(phenylmethyl)-3-pyrrolidinecarboxylate；ethyl (3R,4S)-1-benzyl-4-(2-methylpropyl)pyrrolidine-3-carboxylate
• CAS: 261896-41-7
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: HLSHZFREJKKUQG-SJORKVTESA-N

物化性质

• 沸点：
  361.7±35.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (cis)-1-benzyl-4-isobutyl-pyrrolidine-3-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 反应 5.67h， 生成 cis-4-(S)-isobutylpyrrolidine-3-(R)-carboxylic acid ethyl ester (R,R)-tartaric acid salt
  参考文献：
  名称：

  Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers

  摘要：

  All four possible stereoisomers of the 3-carboxyl-4-isopropyl-pyrrolidine (4) were prepared and their stereochemistry was assigned unambiguously. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00549-x
• 作为产物：
  描述：

  5-methyl-hex-2-ynoic acid ethyl ester 在 Pd-BaSO₄ 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 (cis)-1-benzyl-4-isobutyl-pyrrolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers

  摘要：

  All four possible stereoisomers of the 3-carboxyl-4-isopropyl-pyrrolidine (4) were prepared and their stereochemistry was assigned unambiguously. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00549-x

文献信息

• Branched alkyl pyrrolidine-3-carboxylic acids
  申请人：Warner-Lambert Company

  公开号：US06245801B1

  公开（公告）日：2001-06-12

  Branched alkyl pyrrolidines of formula (I) are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropatnological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.

  公开了式(I)的分支烷基吡咯烷，并且它们在治疗癫痫、晕厥发作、低动力症、颅内疾病、神经退行性疾病、抑郁症、焦虑症、惊恐症、疼痛和神经病理学疾病方面有用。还公开了制备过程和制备中有用的中间体。
• BRANCHED ALKYL PYRROLIDINE-3-CARBOXYLIC ACIDS
  申请人：Warner-Lambert Company LLC

  公开号：EP1112253B1

  公开（公告）日：2004-10-20
• US6245801B1
  申请人：——

  公开号：US6245801B1

  公开（公告）日：2001-06-12
• [EN] BRANCHED ALKYL PYRROLIDINE-3-CARBOXYLIC ACIDS<br/>[FR] ACIDES PYRROLIDINE-3-CARBOXYLIQUES D'ALKYLE RAMIFIE
  申请人：WARNER LAMBERT CO

  公开号：WO2000015611A1

  公开（公告）日：2000-03-23

  Branched alkyl pyrrolidines of formula (I) are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropathological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.
• Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers
  作者：Rong Ling、I.Victor Ekhato、J.Ronald Rubin、David J Wustrow

  DOI：10.1016/s0040-4020(01)00549-x

  日期：2001.7

  All four possible stereoisomers of the 3-carboxyl-4-isopropyl-pyrrolidine (4) were prepared and their stereochemistry was assigned unambiguously. (C) 2001 Elsevier Science Ltd. All rights reserved.