(R)-indoline-2-carboxylic acid methyl ester | 293737-30-1

• 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: (R)-indoline-2-carboxylic acid methyl ester
• 英文别名: (R)-methyl indoline-2-carboxylate；methyl (R)-indoline-2-carboxylate；methyl (2R)-2,3-dihydro-1H-indole-2-carboxylate
• CAS: 293737-30-1
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: URORFKDEPJFPOV-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-methyl-N-(2-(3-oxo-3-(1-phenyl-1H-imidazol-2-yl)propyl)phenyl)benzenesulfonamide 在 甲醇 、 叔丁基过氧化氢 、 C₈₈H₄₈F₂₄N⁽¹⁺⁾*I^(1-) 、 magnesium 作用下， 以 癸烷 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 33.0h， 生成 (R)-indoline-2-carboxylic acid methyl ester
  参考文献：
  名称：

  JP6115946

  摘要：

  公开号：

文献信息

• Fused bicyclic carboxamide derivatives and methods of their use
  申请人：Dolle E. Roland

  公开号：US20050054630A1

  公开（公告）日：2005-03-10

  Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.

  揭示了融合的双环羧酰胺衍生物。还公开了含有这些化合物的药物组合物以及它们的使用方法。
• Stereoselective synthesis of optically active cyclic α- and β-amino esters through lipase-catalyzed transesterification or interesterification processes
  作者：Sergio Alatorre-Santamaría、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1016/j.tetasy.2010.08.002

  日期：2010.9

  A series of cyclic α- and β-amino esters belonging to a family of indolines and quinolines have been efficiently synthesized to study their behavior in lipase-mediated kinetic resolution reactions. The influence of the fused ring structure to the benzene ring and the position of the ester functionality relative to the amino group have been demonstrated, finding excellent values of enantiodiscrimination

  已经有效地合成了属于吲哚啉和喹啉家族的一系列环状α-和β-氨基酯，以研究它们在脂肪酶介导的动力学拆分反应中的行为。已经证明了稠合环结构对苯环的影响以及酯官能度相对于氨基的位置，在念珠菌催化的吲哚-3-羧酸甲酯与正丁醇的酯交换反应中发现了出色的对映异构化值。南极洲观察到脂肪酶B。另一方面，当在烷氧基羰基化，酯交换反应或酯交换反应中使用多种脂酶对吲哚-2-羧酸甲酯或1,2,3,4-四氢喹啉衍生物使用脂肪酶时，发现选择性低至中等。
• [EN] METHOD FOR PREPARING (S)-INDOLINE-2-CARBOXYLIC ACID AND (S)-INDOLINE-2-CARBOXYLIC ACID METHYL ESTER USING HYDROLYTIC ENZYME<br/>[FR] METHODE DE PREPARATION D'UN ACIDE CARBOXYLIQUE (S)-INDOLINE-2 ET D'UN ESTER DE METHYLE D'ACIDE CARBOXYLIQUE (S)-INDOLINE-2 A L'AIDE D'UNE ENZYME HYDROLYTIQUE
  申请人：SK CORP

  公开号：WO2005051910A1

  公开（公告）日：2005-06-09

  Disclosed is a method for preparing (S)-indoline-2-carboxylic acid and (S)-indoline-2-carboxylic acid methyl ester using an inexpensive industrially available enzyme capable of assuring superior optical purity and yield. At this time, the hydrolytic enzyme is selected from the group consisting of Savinase, Alcalase, Novozym 243, Everlase, Esperase, Protease 7 and Acylase, whereby (S)-indoline-2-carboxylic acid and methyl ester thereof having an optical purity of at least 99%e.e. can be obtained through a simplified preparation process, thus generating economic benefits.

  本发明公开了一种使用廉价工业可得酶制备（S）-吲哚-2-羧酸和（S）-吲哚-2-羧酸甲酯的方法，该方法能够保证卓越的光学纯度和产率。在此时，水解酶被选择自Savinase，Alcalase，Novozym 243，Everlase，Esperase，Protease 7和Acylase等组中，通过简化的制备过程，可以获得具有至少99%e.e.的光学纯度的（S）-吲哚-2-羧酸和其甲酯，从而产生经济效益。
• Method for preparing (s)-indoline-2-carboxylic acid and (s)-indoline-2-carboxylic acid methyl ester using hydrolytic enzyme
  申请人：Cho Ryune Nahm

  公开号：US20070077632A1

  公开（公告）日：2007-04-05

  Disclosed is a method for preparing (S)-indoline-2-carboxylic acid and (S)-indoline-2-carboxylic acid methyl ester using an inexpensive industrially available enzyme capable of assuring superior optical purity and yield. At this time, the hydrolytic enzyme is selected from the group consisting of Savinase, Alcalase, Novozym 243, Everlase, Esperase, Protease 7 and Acylase, whereby (S)-indoline-2-carboxylic acid and methyl ester thereof having an optical purity of at least 99% e.e. can be obtained through a simplified preparation process, thus generating economic benefits.

  本发明公开了一种使用一种廉价的工业可得酶制备（S）-吲哚-2-羧酸和（S）-吲哚-2-羧酸甲酯的方法，该酶能够保证卓越的光学纯度和收率。此时，水解酶被选择自Savinase、Alcalase、Novozym 243、Everlase、Esperase、Protease 7和Acylase的组合中，通过简化的制备过程可以获得光学纯度至少为99% e.e.的（S）-吲哚-2-羧酸及其甲酯，从而产生经济效益。
• Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution
  作者：Sergio Alatorre-Santamaría、María Rodriguez-Mata、Vicente Gotor-Fernández、Marcos Carlos de Mattos、Francisco J. Sayago、Ana I. Jiménez、Carlos Cativiela、Vicente Gotor

  DOI：10.1016/j.tetasy.2008.06.010

  日期：2008.7

  A series of alpha-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate. (C) 2008 Elsevier Ltd. All rights reserved.