(1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol | 221910-76-5

• 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: (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol
• 英文别名: (1S,4R)-4-benzyloxycarbonylamino-2-cyclopentenol；Benzyl ((1R,4S)-rel-4-hydroxycyclopent-2-en-1-yl)carbamate；benzyl N-[(1R,4S)-4-hydroxycyclopent-2-en-1-yl]carbamate
• CAS: 221910-76-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: QIVSXTSYXODYSG-NWDGAFQWSA-N

物化性质

• 沸点：
  421.9±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol 在 咪唑 、 盐酸 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 jones reagent 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 四氢呋喃 、 二苯醚 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 0.75h， 生成 1-(benzyloxycarbonyl)kainic acid dimethyl ester
  参考文献：
  名称：

  通往（-）-海藻酸的简明路线。

  摘要：

  通过同时进行Chugaev合成消除和分子内烯类反应作为关键步骤，已经设计了从对映体纯（+）-顺式4-碳四苯甲氧基氨基-2-环戊烯醇制得（-）-海藻酸的简明路线。

  DOI：

  10.1021/ol006377r
• 作为产物：
  描述：

  3-噁-2-氮杂双环[2.2.1]-5-庚烯-2-羧酸苄酯 在 hexacarbonyl molybdenum 、 lipase AK (pseudomonas fluorescens, Amano) 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol
  参考文献：
  名称：

  通往（-）-海藻酸的简明路线。

  摘要：

  通过同时进行Chugaev合成消除和分子内烯类反应作为关键步骤，已经设计了从对映体纯（+）-顺式4-碳四苯甲氧基氨基-2-环戊烯醇制得（-）-海藻酸的简明路线。

  DOI：

  10.1021/ol006377r

文献信息

• Enzymatic Resolution of Aminocyclopentenols as Precursors to <scp>d</scp>- and <scp>l</scp>-Carbocyclic Nucleosides
  作者：Mark J. Mulvihill、Jennifer L. Gage、Marvin J. Miller

  DOI：10.1021/jo972265a

  日期：1998.5.1

  Racemic cis-4-aminocyclopent-2-en-1-ols were synthesized in three steps utilizing hetero Diels-Alder chemistry. Starting from suitably protected hydroxylamines, oxidization with sodium periodate and trapping with cyclopentadiene afforded cycloadducts (+/-)-5a-d. The N-O bond of the cycloadducts was reduced with Mo(CO)(6) to afford (+/-)-cis-4-aminocyclopent-2-en-1-ols (+/-)-6a-d. These compounds, or their corresponding acetates, were kinetically resolved by enzymatic acetylation or hydrolysis, respectively. Enzymatic acetylation of cis-N-(benzylcarbamoyl)-4-aminocyclopent-2-enol [(+/-)-6a] with Candida antarctica B lipase and Pseudomonas species lipase gave the corresponding acetate (-)-7a in 90% and 92% ee, respectively, after 40% conversion. Enzymatic hydrolysis of cis-N-acetyl-4-aminocyclopent-2-enol 1-O-acetate (+/-)-7d with electric eel acetylcholine esterase was successful in providing both cis-N-acetyl-4-aminocyclopent-2-enols (+)ed and (+)-7d in 92% ee (99% ee after a single recrystallization) after 40% conversion. Further synthetic transformations of these resolved synthetic building blocks and derivatives are also reported.
• Enantioselective synthesis of (1 S ,4 R )- N -(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B
  作者：Hui-Jiao Wen、Qing Chen、Guo-Jun Zheng

  DOI：10.1016/j.cclet.2015.07.005

  日期：2015.11

  An efficient biocatalytic process has been developed to obtain optically pure (15,4R)-N-(benzylcarbamoy1)-4-aminocyclopent-2-en-1-ol which can be used as the key intermediate of ticagrelor. In this research, several N-(benzylcarbamoy1)-4-aminocyclopent-2-en-1-ol derivatives have been investigated in which Candida antarctica lipase B (CALB) was used to catalyze the asymmetric hydrolysis reaction. As expected, some of these substrates successfully gave (1S,4R)-N-(benzylcarbamoy1)-4-aminocyclopent2-en-1-ol in >98% enantiomeric excess (ee) with conversion yields up to 45%. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• An asymmetric synthesis of (1S,4R)-4-amino-2-cyclopentenol derivatives
  作者：Masatoshi Asami、Megumi Ogawa、Seiichi Inoue

  DOI：10.1016/s0040-4039(99)00002-7

  日期：1999.2

  A highly enantioselective deprotonation of cis-4-aminocyclopentene oxide derivatives 1 was achieved by using a chiral lithium amide, prepared from (2S,3aS,7aS)-2-(pyrrolidin-1-ylmethyl) octahydroindole, (1S,4R)-4-Amino-2-cyclopentenol derivative 2 was obtained in up to 90 % ee. (C) 1999 Elsevier Science Ltd. All rights reserved.
• EP0865439A4
  申请人：——

  公开号：EP0865439A4

  公开（公告）日：1998-11-11
• COMBINATORIAL LIBRARIES HAVING AMINODIOL MONOMER SUBUNITS
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0865439A1

  公开（公告）日：1998-09-23