2-methylindoline allyl carbamate | 917377-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-methylindoline allyl carbamate
• 英文别名: N-allyloxycarbonyl-2-methylindoline；Prop-2-enyl 2-methyl-2,3-dihydroindole-1-carboxylate
• CAS: 917377-80-1
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: LNCXZRVCAYFRJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylindoline allyl carbamate 在 sodium hydroxide 、 LiAlH4 作用下， 以 水 为溶剂， 生成 1,2-二甲基吲哚啉
  参考文献：
  名称：

  Enantioselection of amines using homocarbonates with hydrolase

  摘要：

  外消旋胺通过对映选择性的碳酰胺化酶转化为手性碳酸酯。简单的同分异构体碳酸酯被用作底物。然后可以去保护手性碳酸酯以得到手性形式的原始胺。或者，手性碳酸酯可以还原以产生甲基化的手性胺。

  公开号：

  US05981267A1
• 作为产物：
  描述：

  氯甲酸烯丙酯 、 2-甲基吲哚啉 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到2-methylindoline allyl carbamate
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active secondary amines: a new efficient route to enantiomerically pure indolines

  摘要：

  An efficient chentoenzymatic route for the synthesis of optically active substituted indolines has been developed. Different lipases have been tested in the alkoxycarbonylation of these secondary amines, Candida antarctica lipase A (CAL-A) was found to be the best biocatalyst for 2-substituted-indolines, and C antarctica lipase B (CAL-B) for 3-methylindoline. The combination of lipases with a variety of allyl carbonates and tert-butyl methyl ether (TBME) as solvent has allowed the isolation of the carbamate and amine derivatives with a high level of enantiopurity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.012

文献信息

• US5981267A
  申请人：——

  公开号：US5981267A

  公开（公告）日：1999-11-09
• Chemoenzymatic preparation of optically active secondary amines: a new efficient route to enantiomerically pure indolines
  作者：Vicente Gotor-Fernández、Pedro Fernández-Torres、Vicente Gotor

  DOI：10.1016/j.tetasy.2006.08.012

  日期：2006.10

  An efficient chentoenzymatic route for the synthesis of optically active substituted indolines has been developed. Different lipases have been tested in the alkoxycarbonylation of these secondary amines, Candida antarctica lipase A (CAL-A) was found to be the best biocatalyst for 2-substituted-indolines, and C antarctica lipase B (CAL-B) for 3-methylindoline. The combination of lipases with a variety of allyl carbonates and tert-butyl methyl ether (TBME) as solvent has allowed the isolation of the carbamate and amine derivatives with a high level of enantiopurity. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantioselection of amines using homocarbonates with hydrolase
  申请人：The Scripps Research Institute

  公开号：US05981267A1

  公开（公告）日：1999-11-09

  Racemic amines are enzymically converted by enantioselective carbamation to produce to chiral carbamates. Simple homocarbonates employed as substrates. The chiral carbamates may then be deprotected to yield the original amine in a chiral form. Alternatively, the chiral carbamates may be reduced so as to produce methylated chiral amines.

  外消旋胺通过对映选择性的碳酰胺化酶转化为手性碳酸酯。简单的同分异构体碳酸酯被用作底物。然后可以去保护手性碳酸酯以得到手性形式的原始胺。或者，手性碳酸酯可以还原以产生甲基化的手性胺。