(1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid; hydrochloride | 947601-81-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基酸盐
• 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: (1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid; hydrochloride
• 英文别名: (1S,2S,3R,4R)-(+)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid hydrochloride；(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid;hydrochloride
• CAS: 947601-81-2
• 化学式: C₈H₁₁NO₂*ClH
• 分子量: 189.642
• InChiKey: JZBHUJIMERBHKY-BZUDZRPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid; hydrochloride 在 甲醇 、 sodium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 (rac-di-exo)-3-(3,3-dimethylbutylamino)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  WO2008/124450

  摘要：

  公开号：
• 作为产物：
  描述：

  (1R,2R,5S,6S)-3-azatricyclo[4.2.1.0^2,5]non-7-en-4-one 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以84%的产率得到(1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid; hydrochloride
  参考文献：
  名称：

  Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of β-lactams

  摘要：

  1, 4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.0(2.5)]nonan-4-one, (+/-)-1, and exo-3-azatricyclo[4.2.1.0(2.5)]non-7-en-4-one, (+/-)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1 equiv of H2O in diisopropyl ether at 70degreesC. The resolved beta-amino acids 1a and 2a (yield,46%) and beta-lactams 1b and 2b (yield greater than or equal to40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding beta-amino acid hydrochloride enantiomers (ee greater than or equal to98%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.034

文献信息

• US2014/256976
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] A. PROCESS FOR THE PREPARATION OF AMINOACRYLIC ACID DERIVATIVES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS D'ACIDE AMINOACRYLIQUE
  申请人：COUNCIL OF SCIENT & IND RES AN INDIAN REGISTERED BODY INC UNDER THE REGISTRATION OF SOCIETIES ACT AC

  公开号：WO2013054366A8

  公开（公告）日：2013-05-30
• WO2008/124450
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of β-lactams
  作者：Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2003.12.034

  日期：2004.2

  1, 4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.0(2.5)]nonan-4-one, (+/-)-1, and exo-3-azatricyclo[4.2.1.0(2.5)]non-7-en-4-one, (+/-)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1 equiv of H2O in diisopropyl ether at 70degreesC. The resolved beta-amino acids 1a and 2a (yield,46%) and beta-lactams 1b and 2b (yield greater than or equal to40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding beta-amino acid hydrochloride enantiomers (ee greater than or equal to98%). (C) 2004 Elsevier Ltd. All rights reserved.