glycine tert-butyl ester, p-chlorobenzaldehyde Schiff base | 1067975-40-9

• 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: glycine tert-butyl ester, p-chlorobenzaldehyde Schiff base
• 英文别名: (E)-N-(4-chlorophenyl)methyleneglycine t-butyl ester
• CAS: 1067975-40-9
• 化学式: C₁₃H₁₆ClNO₂
• 分子量: 253.729
• InChiKey: HSIDOHKQHALOQR-OVCLIPMQSA-N

物化性质

• 沸点：
  322.2±27.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  glycine tert-butyl ester, p-chlorobenzaldehyde Schiff base 在 盐酸 、 氢氧化钾 、 chiral binaphthyl-based ammonium salt 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 L-苯基丙氨酸叔丁酯
  参考文献：
  名称：

  Highly enantioselective monoalkylation of p-chlorobenzaldehyde imine of glycine tert-butyl ester under mild phase-transfer conditions

  摘要：

  The selective monoalkylation of glycine tert-butyl ester aldimine Schiff base 3 has been realized in high chemical yield with excellent enantioselectivity under mild liquid-liquid phase-transfer conditions by the use of binaphthyl-derived chiral quaternary ammonium bromides 7 and 8 as catalysts. This achievement demonstrates that 3 can be used as a cost-effective substrate for the preparation of optically active alpha-alkyl-alpha-amino, acid derivatives by chiral phase-transfer catalysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.019
• 作为产物：
  描述：

  甘氨酸叔丁酯 、 4-氯苯甲醛 在 magnesium sulfate 作用下， 以 甲醇 为溶剂， 生成 glycine tert-butyl ester, p-chlorobenzaldehyde Schiff base
  参考文献：
  名称：

  Highly enantioselective monoalkylation of p-chlorobenzaldehyde imine of glycine tert-butyl ester under mild phase-transfer conditions

  摘要：

  The selective monoalkylation of glycine tert-butyl ester aldimine Schiff base 3 has been realized in high chemical yield with excellent enantioselectivity under mild liquid-liquid phase-transfer conditions by the use of binaphthyl-derived chiral quaternary ammonium bromides 7 and 8 as catalysts. This achievement demonstrates that 3 can be used as a cost-effective substrate for the preparation of optically active alpha-alkyl-alpha-amino, acid derivatives by chiral phase-transfer catalysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.019

文献信息

• Design of new, chiral phase-transfer catalysts for practical, catalytic asymmetric synthesis
  作者：Keiji Maruoka

  DOI：10.1016/s0022-1139(01)00472-9

  日期：2001.11

  Structurally rigid, chiral spiro ammonium salts of type 1 derived from commercially available (S)-binaphthol have been designed as a new C2-symmetric chiral phase-transfer catalyst and successfully applied to the highly efficient, catalytic enantioselective alkylation of tert-butyl glycinate Schiff base under mild phase-transfer conditions to furnish α-alkyl-α-amino acids and α,α-dialkyl-α-amino acids with excellent

  衍生自商业可获得的（S）-联萘酚的1型结构刚性手性螺环铵盐已被设计为一种新型的C 2对称手性相转移催化剂，已成功地用于甘氨酸叔丁酯的高效催化对映选择性烷基化Schiff碱在温和的相转移条件下可提供具有出色对映选择性的α-烷基-α-氨基酸和α，α-二烷基-α-氨基酸。这些铵盐也已用于原位生成手性季铵氟化物。
• ARGINASE INHIBITORS AND METHODS OF USE
  申请人：CHRISTIANSON DAVID W.

  公开号：US20100189644A1

  公开（公告）日：2010-07-29

  The present invention is directed to arginase inhibitor compounds of formula IA or formula IB: or a pharmaceutically acceptable salt thereof, compositions containing these compounds, and methods of their use for the treatment and diagnosis of conditions characterized by upregulation of arginase, abnormally high arginase activity, or by abnormally low nitric oxide synthase activity.

  本发明涉及化合物IA或化合物IB的抑制剂，或其药用盐，含有这些化合物的组合物，以及用于治疗和诊断由精氨酸酶上调、异常高的精氨酸酶活性或异常低的一氧化氮合酶活性所特征的疾病的方法。
• Organocatalytic Asymmetric Conjugate Additions to Cyclopent‐1‐enecarbaldehyde: A Critical Assessment of Organocatalytic Approaches towards the Telaprevir Bicyclic Core
  作者：Luca Bernardi、Mariafrancesca Fochi、Riccardo Carbone、Ada Martinelli、Martin E. Fox、Christopher J. Cobley、Bhaskar Kandagatla、Srinivas Oruganti、Vilas H. Dahanukar、Armando Carlone

  DOI：10.1002/chem.201503352

  日期：2015.12.21

  In the context of a programme directed at the manufacture of telaprevir, eight possible approaches to its bicyclic α‐amino acid core, based on organocatalytic enantioselective conjugate additions to cyclopent‐1‐enecarbaldehyde, were identified and preliminarily explored. Four reactions, delivering advanced intermediates en route to the target amino acid, were selected for a thorough optimisation. Three

  在针对telaprevir的生产计划的背景下，基于对环戊-1-烯甲醛的有机催化对映选择性共轭加成反应，确定并初步探索了八种可能的双环α-氨基酸核心途径。为了全面优化，选择了四个反应，这些反应在向目标氨基酸的途中提供了先进的中间体。此反应中的三个涉及用脯氨醇催化剂（添加硝基甲烷，硝基乙酸盐和乙酰氨基丙酸盐）进行亚胺离子催化，一个基于金鸡纳衍生的相转移催化剂（添加甘氨酸亚胺）。在某些情况下，精心选择添加剂可将催化剂负载量降低至0.5 mol％。通过利用现成的底物和催化剂，制备能够以高收率和对映选择性接近特拉匹韦的核心的中间体，突显了有机催化技术在经济高效地制备药物方面的潜力。
• Arginase Inhibitors and Methods of Use Thereof
  申请人：Tomczuk Bruce Edward

  公开号：US20120171116A1

  公开（公告）日：2012-07-05

  The present invention includes arginase enzyme inhibitors, compositions comprising these arginase inhibitors, and methods of treating or diagnosing conditions characterized either by abnormally high arginase activity or abnormally low nitric oxide levels in a mammal, comprising administering compositions of the invention to the mammal.

  本发明包括精氨酸酶抑制剂，包括这些精氨酶抑制剂的组合物，以及治疗或诊断以哺乳动物体内精氨酶活性异常高或一氧化氮水平异常低为特征的疾病的方法，包括将本发明的组合物给哺乳动物进行治疗。
• METHOD FOR PRODUCING OPTICALLY ACTIVE 1-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ESTER
  申请人：Aikawa Toshiaki

  公开号：US20120130116A1

  公开（公告）日：2012-05-24

  1-Amino-2-vinylcyclopropanecarboxylic acid ester, which is useful as a synthetic intermediate of pharmaceuticals, can be produced by a process of producing 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4): including a step of hydrolysis of an optically active 1-N-(arylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (3): which is obtained by reacting an N-(arylmethylene)glycine ester represented by formula (1): with a compound represented by formula (2): in the presence of a base and an optically active quaternary ammonium salt.

  1-氨基-2-乙烯基环丙烷羧酸酯是一种用作制药合成中间体的化合物，可以通过以下步骤制备：首先，将化合物（2）与代表式（1）的N-(芳基亚甲基)甘氨酸酯在碱和手性季铵盐的存在下反应，得到代表式（3）的手性1-N-(芳基亚甲基)氨基-2-乙烯基环丙烷羧酸酯；然后，对该化合物进行水解反应，得到代表式（4）的1-氨基-2-乙烯基环丙烷羧酸酯，该化合物可用作制药合成中间体。