(S)-(+)-4-isopropylthiazolidine-3-carboxylic acid tert-butyl ester | 259257-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-(+)-4-isopropylthiazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: (S)-3-tert-butoxycarbonyl-4-isopropylthiazolidine；tert-butyl (4S)-4-propan-2-yl-1,3-thiazolidine-3-carboxylate
• CAS: 259257-86-8
• 化学式: C₁₁H₂₁NO₂S
• 分子量: 231.359
• InChiKey: XSCPFIJEAGOHEE-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-4-isopropylthiazolidine-3-carboxylic acid tert-butyl ester 在 正丁基锂 、 氘代甲醇-d 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以95%的产率得到
  参考文献：
  名称：

  10.1016/s0957-4166(00)00154-3

  摘要：

  DOI：

  10.1016/s0957-4166(00)00154-3
• 作为产物：
  描述：

  N-Boc-L-缬氨醇 在 盐酸 、 氢氧化钾 、 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 590.5h， 生成 (S)-(+)-4-isopropylthiazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Computer-assisted discovery of novel amino acid derived sulfides for enantioselective epoxidation of aldehydes

  摘要：

  With the aid of molecular modeling, thiazolidine derivatives have been designed as catalysts for epoxidation of aldehydes. Accessible from amino acids, the thiazolidine derivatives can be synthesized in both enantiomeric forms and with a diverse array of substituents. A representative member, (S)-N-tert-butoxycarbonyl-2,2-dimethyl-4- isopropyl thiazolidine, of the thiazolidine family has been prepared, and it has been shown to catalyze the formation of trans-stilbene oxide with high enantioselectivity. Experimental and theoretical characterization has allowed the evaluation of the factors affecting enantioselectivity, facilitating the design of second-generation thiazolidines and other chiral sulfides as epoxidation catalysts. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00396-9

文献信息

• [EN] ENANTIOSELECTIVE CHIRAL SULPHIDE CATALYSTS AND A METHOD FOR THE MANUFACTURE THEREOF<br/>[FR] CATALYSEURS SULFURES, CHIRAUX ET ENANTIOSELECTIFS ET LEUR PROCEDE DE FABRICATION
  申请人：NESTE CHEMICALS OY

  公开号：WO2000010985A1

  公开（公告）日：2000-03-02

  The invention relates to a chiral sulphide catalyst, having the structure of formula (IIa) or (IIb) or (IIc) or (IId), wherein X represents a hydrogen atom, alkyl, alkoxy, aryl or alkylaryl group, or a dialkyl nitrogen; Y is a side chain present in amino acids of naturally occurring proteins, in other non-protein amino acids, or in amino acids not occuring naturally, having formula (III), or Y forms with the nitrogen atom a ring having 4 to 10 carbon and/or hereto atoms. Further, the invention is directed to a method for producting such a catalyst, and the use of said catalyst.
• Computer-assisted discovery of novel amino acid derived sulfides for enantioselective epoxidation of aldehydes
  作者：Vesa T Myllymäki、Mika K Lindvall、Ari M.P Koskinen

  DOI：10.1016/s0040-4020(01)00396-9

  日期：2001.5

  With the aid of molecular modeling, thiazolidine derivatives have been designed as catalysts for epoxidation of aldehydes. Accessible from amino acids, the thiazolidine derivatives can be synthesized in both enantiomeric forms and with a diverse array of substituents. A representative member, (S)-N-tert-butoxycarbonyl-2,2-dimethyl-4- isopropyl thiazolidine, of the thiazolidine family has been prepared, and it has been shown to catalyze the formation of trans-stilbene oxide with high enantioselectivity. Experimental and theoretical characterization has allowed the evaluation of the factors affecting enantioselectivity, facilitating the design of second-generation thiazolidines and other chiral sulfides as epoxidation catalysts. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 10.1016/s0957-4166(00)00154-3
  作者：Gawley, Robert E.、Zhang, Qianhui、McPhail, Andrew T.

  DOI：10.1016/s0957-4166(00)00154-3

  日期：——