2--amino-1-carbobenzoxycyclopentene | 163705-82-6

• 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: 2--amino-1-carbobenzoxycyclopentene
• 英文别名: benzyl 2-[[(1R)-1-phenylethyl]amino]cyclopentene-1-carboxylate
• CAS: 163705-82-6
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: XEINCMMNGUPYFT-MRXNPFEDSA-N

物化性质

• 沸点：
  470.9±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2--amino-1-carbobenzoxycyclopentene 在 palladium dihydroxide sodium tetrahydroborate 、 氢气 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 生成 (1S,2R)-2-氨基环戊烷甲酸
  参考文献：
  名称：

  Diastereo and enantioselective entry to β-amino esters by hydride reduction of homochiral β-enamino esters.

  摘要：

  The reduction of homochiral beta-enamino esters 1 with sodium triacetoxyborohydride, which occurs with good diastereo- and enantioselectivity in the beta-amino esters 2, is described. This procedure allows a straightforward preparation of compounds with known biological activity.

  DOI：

  10.1016/0957-4166(94)80111-8
• 作为产物：
  描述：

  环戊羧酸,2-羰基-,苯基甲基酯 、 R(+)-alpha-甲基苄胺 在 aluminum oxide 、 5A molecular sieve 、 silica gel 作用下， 以 环己烷 为溶剂， 反应 72.0h， 生成 2--amino-1-carbobenzoxycyclopentene
  参考文献：
  名称：

  The asymmetric Michael-type alkylation of chiral β-enamino esters: critical role of a benzyl ester group in the racemization of adducts

  摘要：

  In contrast with keto diester (R)-10a bearing a methyl ester group at the quaternary carbon center, the benzyl ester analogue (R)-10a partially racemized during workup, thereby revealing that the nature of the ester group at the quaternary carbon center has a critical role in the rate of racemization of such Michael adducts. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.034

文献信息

• A versatile route to β-enamino esters by acylation of lithium enamines with diethyl carbonate or benzyl chloroformate
  作者：Giuseppe Bartoli、Cristina Cimarelli、Renato Dalpozzo、Gianni Palmieri

  DOI：10.1016/0040-4020(95)00476-o

  日期：1995.7

  route to β-enamino esters 1, using accessible starting materials, was developed. Lithiated enamines are allowed to react with diethyl carbonate or benzyl chloroformate with the formation of the β-enamino esters 1a or 1b. The reaction is rather general from a wide array of ketimines and aldimines. Products included cyclic β-enamino esters 1aa-ac, very useful for the synthesis of natural products.

  开发了一种使用易得的起始原料制备β-烯胺酯1的通用方法。使锂化的烯胺与碳酸二乙酯或氯甲酸苄酯反应，形成β-烯氨基酯1a或1b。来自各种各样的酮亚胺和醛亚胺的反应相当普遍。产品包括环状β-烯胺酯1aa-ac，对合成天然产物非常有用。
• 10.3998/ark.5550190.0018.400
  作者：Seck, Rokhayatou、Gassama, Abdoulaye、Nour, Mohammed、Demange, Luc、Cavé, Christian

  DOI：10.3998/ark.5550190.0018.400

  日期：——
• AN IMPROVED SYNTHESIS OF ENANTIOPURE β-AMINO ACIDS
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1081/scc-100105666

  日期：2001.1

  An improved method for the preparation of both the enantiopure beta -amino acids is presented. The diastereomer benzyl beta -amino esters, obtained by stereoselective reduction of beta -enamino esters, were separated and hydrogenolyzed to the free enantiopure beta -amino acids.
• Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters
  作者：Cristina Cimarelli、Gianni Palmieri

  DOI：10.1021/jo960107y

  日期：1996.1.1

  The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.