(S)-N-(tert-butoxycarbonyl)-4-(2',2'-dibromoethenyl)-2,2,4-trimethyl-3-oxazolidine

• 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)-N-(tert-butoxycarbonyl)-4-(2',2'-dibromoethenyl)-2,2,4-trimethyl-3-oxazolidine
• 英文别名: 3-t-Butoxycarbonyl-2,2-dimethyl-(4S)-(2,2-dibromo)ethenyl-4-methyloxazolidine；3-t-Butoxycarbonyl-2, 2-dimethyl-(4S)-(2,2-dibromo)ethenyl-4-methyloxazolidine；tert-butyl (4S)-4-(2,2-dibromoethenyl)-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
• 化学式: C₁₃H₂₁Br₂NO₃
• 分子量: 399.123
• InChiKey: POEHRGVMNMOODJ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ammonium chloride 、 (S)-N-(tert-butoxycarbonyl)-4-(2',2'-dibromoethenyl)-2,2,4-trimethyl-3-oxazolidine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到3-t-Butoxycarbonyl-2, 2-dimethyl-(4S)-ethynyl-4-methyloxazolidine
  参考文献：
  名称：

  AMINO ALCOHOL DERIVATIVES

  摘要：

  公开号：

  EP1300405B1
• 作为产物：
  描述：

  三溴甲烷 、 (R)-N-(tert-butoxycarbonyl)-4-formyl-2,2,4-trimethyl-3-oxazolidine 在 potassium tert-butylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以79%的产率得到(S)-N-(tert-butoxycarbonyl)-4-(2',2'-dibromoethenyl)-2,2,4-trimethyl-3-oxazolidine
  参考文献：
  名称：

  A straightforward synthesis of both enantiomers of α-vinylalanine and α-ethynylalanine

  摘要：

  This report describes the synthesis of enantiomerically pure (S)- and (R)-alpha-vinylalanines and (S)- and (R)-alpha-ethynylalanines, four quaternary alpha-amino acids, using a straightforward synthetic route and starting from (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00533-9

文献信息

• Amino alcohol derivatives
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20030236297A1

  公开（公告）日：2003-12-25

  Compounds of formula (I) which exhibit excellent immune suppression activity, pharmacologically acceptable salts thereof, esters thereof or other derivatives: 1 wherein R 1 and R 2 are a hydrogen atom, an amino protecting group; R 3 is a hydrogen atom, a hydroxy protecting group; R 4 is a lower alkyl group; n is an integer from 1 to 6; X is an ethylene group; Y is a C 1 -C 10 alkylene group, a C 1 -C 10 alkylene group substituted with 1 to 3 substituents selected from substituent group a and b; R 5 is an aryl group; R 6 and R 7 are a hydrogen atom, a group selected from substituent group a; with the proviso when R 5 is a hydrogen atom, Y is not a single bond or a straight chain C 1 -C 10 alkylene group.

  式（I）的化合物表现出优异的免疫抑制活性，其药理学上可接受的盐，酯或其他衍生物：其中R1和R2是氢原子，氨基保护基；R3是氢原子，羟基保护基；R4是较低的烷基基团；n是1到6之间的整数；X是乙烯基团；Y是C1-C10烷基基团，带有1到3个从取代基a和b中选择的取代基的C1-C10烷基基团；R5是芳基基团；R6和R7是氢原子，从取代基a中选择的基团；但是当R5是氢原子时，Y不是单键或直链的C1-C10烷基基团。
• US6723745B2
  申请人：——

  公开号：US6723745B2

  公开（公告）日：2004-04-20
• US6964976B2
  申请人：——

  公开号：US6964976B2

  公开（公告）日：2005-11-15
• AMINO ALCOHOL DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP1300405B1

  公开（公告）日：2007-04-18
• A straightforward synthesis of both enantiomers of α-vinylalanine and α-ethynylalanine
  作者：Alberto Avenoza、Carlos Cativiela、Jesús M Peregrina、David Sucunza、Marı́a M Zurbano

  DOI：10.1016/s0957-4166(99)00533-9

  日期：1999.12

  This report describes the synthesis of enantiomerically pure (S)- and (R)-alpha-vinylalanines and (S)- and (R)-alpha-ethynylalanines, four quaternary alpha-amino acids, using a straightforward synthetic route and starting from (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.