1-[(S)-2-(叔-丁氧基羰基)-3-(2-甲氧基乙氧基)丙基]环戊羧酸环己基铵 | 167944-94-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-[(S)-2-(叔-丁氧基羰基)-3-(2-甲氧基乙氧基)丙基]环戊羧酸环己基铵
• 英文名称: (S)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)-propyl]-1-cyclopentanecarboxylic acid cyclohexylamine salt
• 英文别名: (S)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid cyclohexylamine salt；cyclohexanamine;1-[(2S)-2-(2-methoxyethoxymethyl)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]cyclopentane-1-carboxylic acid
• CAS: 167944-94-7
• 化学式: C₆H₁₃N*C₁₇H₃₀O₆
• 分子量: 429.598
• InChiKey: NJMMIOIKHYTVGG-ZOWNYOTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(2-methoxyethoxymethyl)acrylate 在 [(R)-RuCl(p-cymene)BINAP]Cl 、 氢气 、 碘 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 为溶剂， 50.0 ℃ 、405.33 kPa 条件下， 反应 3.0h， 生成 sodium;1-[3-(2-methoxyethoxy)-2-[(2-methylpropan-2-yl)oxycarbonyl]prop-2-enyl]cyclopentane-1-carboxylate 、 1-[(S)-2-(叔-丁氧基羰基)-3-(2-甲氧基乙氧基)丙基]环戊羧酸环己基铵
  参考文献：
  名称：

  Large-Scale Candoxatril Asymmetric Hydrogenation

  摘要：

  Ruthenium-catalyzed asymmetric hydrogenation was used to prepare tons of a key chiral succinate intermediate for clinical trials quantities of candoxatril. MeOBiphep was used as the ligand, and the catalyst was generated in situ from RuCOD-Bismethylallyl. THF was the best cosolvent for the reaction leading to a selective hydrogenation and a process which was readily amenable on large scale.

  DOI：

  10.1021/op010005w

文献信息

• Hydrogenation
  申请人：Pfizer Inc.

  公开号：US05618970A1

  公开（公告）日：1997-04-08

  Compounds of formula ##STR1## where R is 5-indanyl or a carboxylic acid protecting group, or an amine salt thereof, are prepared by hydrogenating an (E)-allylic ether of formula ##STR2## in the presence of a stereoselective rhodium or ruthenium biphosphine catalyst and a protic solvent.

  化合物的公式为##STR1##其中R是5-吲哚基或羧酸保护基，或其胺盐，通过在立体选择性的铑或钌双膦催化剂和质子溶剂的存在下氢化公式为##STR2##的（E）-烯丙基醚制备。
• Stereoselective synthesis of a candoxatril intermediate asymmetric hydrogenation
  作者：Stephen Challenger、Andrew Derrick、Clive P. Mason、Terry V. Silk

  DOI：10.1016/s0040-4039(98)02687-2

  日期：1999.3

  A four step synthesis of a chiral glutarate half ester intermediate, required for the preparation of candoxatril, has been developed from t-butyl acrylate. The key steps in this route include a stereoselective synthesis of a trisubstituted alkene and its asymmetric hydrogenation with a Ru-BINAP catalyst. (C) 1999 Elsevier Science Ltd. All rights reserved.
• US5618970A
  申请人：——

  公开号：US5618970A

  公开（公告）日：1997-04-08
• Large-Scale Candoxatril Asymmetric Hydrogenation
  作者：Michel Bulliard、Blandine Laboue、Jean Lastennet、Sonia Roussiasse

  DOI：10.1021/op010005w

  日期：2001.7.1

  Ruthenium-catalyzed asymmetric hydrogenation was used to prepare tons of a key chiral succinate intermediate for clinical trials quantities of candoxatril. MeOBiphep was used as the ligand, and the catalyst was generated in situ from RuCOD-Bismethylallyl. THF was the best cosolvent for the reaction leading to a selective hydrogenation and a process which was readily amenable on large scale.