tert-butyl (R)-3-(4-chlorophenyl)-2-(diphenylmethanediylamino)propanoate | 119244-26-7

• 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: tert-butyl (R)-3-(4-chlorophenyl)-2-(diphenylmethanediylamino)propanoate
• 英文别名: tert-butyl (2R)-2-(benzhydrylideneamino)-3-(4-chlorophenyl)propanoate
• CAS: 119244-26-7
• 化学式: C₂₆H₂₆ClNO₂
• 分子量: 419.951
• InChiKey: ZHTASUTYPHSHCY-HSZRJFAPSA-N

物化性质

• 沸点：
  508.0±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-3-(4-chlorophenyl)-2-(diphenylmethanediylamino)propanoate 在 盐酸 作用下， 生成 D-4-氯苯丙氨酸
  参考文献：
  名称：

  The stereoselective synthesis of .alpha.-amino acids by phase-transfer catalysis

  摘要：

  DOI：

  10.1021/ja00188a089
• 作为产物：
  描述：

  N-二苯亚甲基-甘氨酸叔丁酯 、 4-氯苄溴 在 N-(4-nitrophenacyl)cinchonium bromide 氢氧化钾 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 3.0h， 生成 tert-butyl (R)-3-(4-chlorophenyl)-2-(diphenylmethanediylamino)propanoate 、 tert-butyl (S)-3-(4-chlorophenyl)-2-(diphenylmethanediylamino)propanoate
  参考文献：
  名称：

  一类新的苯乙酮基金鸡纳生物碱作为相转移催化剂：在α-氨基酸的对映选择性合成中的应用

  摘要：

  制备了一类新的苯乙酮基金鸡纳生物碱季铵盐，并评估其作为甘氨酸亚胺酯对映选择性烷基化中的相转移催化剂。

  DOI：

  10.1246/cl.2007.1354

文献信息

• Enantioselective reactions of tert-butyl glycinate–benzophenone Schiff base catalyzed by chiral phase-transfer catalyst in aqueous media without any organic solvent
  作者：Nobuyuki Mase、Takahiro Ohno、Hironao Morimoto、Fumito Nitta、Hidemi Yoda、Kunihiko Takabe

  DOI：10.1016/j.tetlet.2005.03.045

  日期：2005.5

  phase-transfer catalyzed enantioselective alkylations of tert-butyl glycinate–benzophenone Schiff base were investigated in aqueous media without any organic solvent. Reactions in aqueous media smoothly proceeded to give the desired product in higher yield than under standard liquid–liquid biphasic conditions. In aqueous media the formation of benzophenone, which was caused by in situ hydrolysis of Schiff

  在没有任何有机溶剂的水性介质中研究了甘氨酸叔丁酯-二苯甲酮席夫碱的手性相转移催化对映选择性烷基化。与标准的液-液两相条件相比，在水性介质中的反应平稳进行，从而以更高的收率得到所需的产物。在水性介质中，抑制了由席夫碱的原位水解引起的二苯甲酮的形成。
• A New Class of Acetophenone-based Cinchona Alkaloids as Phase-transfer Catalysts: Application to the Enantioselective Synthesis of α-Amino Acids
  作者：Jian Lv、Liping Zhang、Lei Liu、Yongmei Wang

  DOI：10.1246/cl.2007.1354

  日期：2007.11.5

  A new class of acetophenone-based cinchona alkaloid-derived quaternary ammonium salts were prepared and evaluated as phase-transfer catalysts in the enantioselective alkylation of glycine imine est...

  制备了一类新的苯乙酮基金鸡纳生物碱季铵盐，并评估其作为甘氨酸亚胺酯对映选择性烷基化中的相转移催化剂。
• A convenient method for asymmetric alkylation of glycine imine esters using solid supports
  作者：Haitao Yu、Hideko Koshima

  DOI：10.1016/j.tetlet.2003.10.023

  日期：2003.12

  A symmetric alkylation of butyl glycinate-benzophenone Schiff base proceeded smoothly on clays and alumina at room temperature to afford alkylated products in high yields and good enantioselectivities. (C) 2003 Elsevier Ltd. All rights reserved.
• Asymmetric alkylation of glycine imine esters using solid supports preloaded with base
  作者：Haitao Yu、Setsuko Takigawa、Hideko Koshima

  DOI：10.1016/j.tet.2004.07.002

  日期：2004.9

  Investigations into the use of solid supports preloaded with base for the asymmetric alkylation of a benzophenone-derived glycine-imine was described. Residual traces of water on the support dramatically accelerated the reactions to complete within a few minutes. The conditions employed in the present synthesis are mild, efficient and general. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of new dimeric-PEG-supported cinchona ammonium salts as chiral phase transfer catalysts for the alkylation of Schiff bases with water as the solvent
  作者：Xin Wang、Liang Yin、Ting Yang、Yongmei Wang

  DOI：10.1016/j.tetasy.2006.12.024

  日期：2007.1

  The water-soluble PEG-supported cinchona ammonium salts were successfully synthesized and used as chiral phase transfer catalysts for the asymmetric alkylation of tert-butyl benzophenone Schiff base derivatives with high chemical yields (up to 98%) and enantio selectivities (up to 97%) in aqueous media. The recycling results showed that the polymers were stable and rarely lost activities. (c) 2007 Elsevier Ltd. All rights reserved.