(3aR,6aR)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-6a-carboxylic acid | 1231766-02-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,6aR)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-6a-carboxylic acid
• 英文别名: (3aR,6aR)-hexahydrocyclopenta[b]pyrrole-1,6a-dicarboxylic acid 1-tert-butyl ester；(3aR,6aR)-1-[(2-methylpropan-2-yl)oxycarbonyl]-2,3,3a,4,5,6-hexahydrocyclopenta[b]pyrrole-6a-carboxylic acid
• CAS: 1231766-02-1
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: UOZUEGTWJWOOGY-NOZJJQNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3aR,6aR)-1-[(1S)-1-phenylethyl]hexahydrocyclopenta[b]pyrrole-6a(1H)-carbonitrile 在 盐酸 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， -10.0~35.0 ℃ 、5.07 MPa 条件下， 反应 126.0h， 生成 (3aR,6aR)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-6a-carboxylic acid
  参考文献：
  名称：

  Synthesis of enantiopure (R,R)- and (S,S)-cis-2,3-propanoprolines

  摘要：

  A novel approach to the synthesis of an enantiopure bicyclic proline analogue, hexahydrocyclopentalb]pyrrole-6a(1H)-carboxylic acid ('2,3-propanoproline'), has been developed. The method relied on tandem Strecker-nucleophilic cyclization reaction of 2-(2-bromoethyl)cyclopentanone. The overall synthetic scheme included six steps and resulted in 18% overall yield of both enantiomers of the title amino acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.017

文献信息

• Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids
  作者：Santos Fustero、Natalia Mateu、Antonio Simón-Fuentes、José Luis Aceña

  DOI：10.1021/ol1010246

  日期：2010.7.2

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.