(1R,2R)-cyclopentane-1,2-dicarboxylic acid bis[(2'-hydroxy-1'-(S)-tert-butylethyl)-amide] | 889888-66-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (1R,2R)-cyclopentane-1,2-dicarboxylic acid bis[(2'-hydroxy-1'-(S)-tert-butylethyl)-amide]
• CAS: 889888-66-8
• 化学式: C₁₉H₃₆N₂O₄
• 分子量: 356.506
• InChiKey: XASGRQRHFMGELF-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  98.66
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-cyclopentane-1,2-dicarboxylic acid bis[(2'-hydroxy-1'-(S)-tert-butylethyl)-amide] 在 二乙胺基三氟化硫 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(1R,2R)-bis-[4'-(S)-tert-butyl-4',5'-dihydro-1',3'-oxazolin-2'-yl]-cyclopentane
  参考文献：
  名称：

  Asymmetric synthesis of chiral bisoxazolines and their use as ligands in metal catalysis

  摘要：

  Novel C-2- and C-1-symmetric chiral bisoxazolines with a cyclic backbone have been synthesized in an asymmetric manner starting from ineso anhydrides. All synthetic steps are easy to perform and lead to the desired products in good overall yields. Preliminary investigations revealed the applicability of these new compounds as ligands in transfer hydrogenations and various metal-catalyzed enantioselective C-C-bond forming reactions such as cyclopropanations and Diels-Alder reactions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.036
• 作为产物：
  描述：

  (1R,2S)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid 在 sodium hydroxide 、 草酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (1R,2R)-cyclopentane-1,2-dicarboxylic acid bis[(2'-hydroxy-1'-(S)-tert-butylethyl)-amide]
  参考文献：
  名称：

  Asymmetric synthesis of chiral bisoxazolines and their use as ligands in metal catalysis

  摘要：

  Novel C-2- and C-1-symmetric chiral bisoxazolines with a cyclic backbone have been synthesized in an asymmetric manner starting from ineso anhydrides. All synthetic steps are easy to perform and lead to the desired products in good overall yields. Preliminary investigations revealed the applicability of these new compounds as ligands in transfer hydrogenations and various metal-catalyzed enantioselective C-C-bond forming reactions such as cyclopropanations and Diels-Alder reactions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.036

文献信息

• Asymmetric synthesis of chiral bisoxazolines and their use as ligands in metal catalysis
  作者：Iuliana Atodiresei、Ingo Schiffers、Carsten Bolm

  DOI：10.1016/j.tetasy.2005.12.036

  日期：2006.2

  Novel C-2- and C-1-symmetric chiral bisoxazolines with a cyclic backbone have been synthesized in an asymmetric manner starting from ineso anhydrides. All synthetic steps are easy to perform and lead to the desired products in good overall yields. Preliminary investigations revealed the applicability of these new compounds as ligands in transfer hydrogenations and various metal-catalyzed enantioselective C-C-bond forming reactions such as cyclopropanations and Diels-Alder reactions. (c) 2006 Elsevier Ltd. All rights reserved.