2-(RS)-(2-bromo-2-propenyl)-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester | 192516-42-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(RS)-(2-bromo-2-propenyl)-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
• 英文别名: (R,S)-(2-Bromo-2-propenyl)-1,4-butanedioic Acid 4-(1,1-Dimethylethyl) 1-Methyl Ester；4-O-tert-butyl 1-O-methyl 2-(2-bromoprop-2-enyl)butanedioate
• CAS: 192516-42-0
• 化学式: C₁₂H₁₉BrO₄
• 分子量: 307.184
• InChiKey: YGROFSOGBIOSQV-UHFFFAOYSA-N

物化性质

• 沸点：
  324.0±42.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(RS)-(2-bromo-2-propenyl)-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (RS)-2-(2-bromo-2-propenyl)-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-benzyl ester
  参考文献：
  名称：

  Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives

  摘要：

  Prochiral discrimination by the biocatalyst Alcalase(R), an enzyme preparation of subtilisin Carlsberg, was used to effect enantio- and regioselective monohydrolysis of a variety of(RS)-2-substituted succinate diesters to afford the corresponding half esters in modest to excellent enantiomeric excesses (>99%). Exploitation of malonate chemistry, as well as recycling of the unhydrolyzed isomer from the enantioselective hydrolysis, has resulted in a process which is both practical and economical. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00330-4
• 作为产物：
  描述：

  dimethyl 2-(2'-bromoallyl)malonate 在 sodium hexamethyldisilazane 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(RS)-(2-bromo-2-propenyl)-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
  参考文献：
  名称：

  Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives

  摘要：

  Prochiral discrimination by the biocatalyst Alcalase(R), an enzyme preparation of subtilisin Carlsberg, was used to effect enantio- and regioselective monohydrolysis of a variety of(RS)-2-substituted succinate diesters to afford the corresponding half esters in modest to excellent enantiomeric excesses (>99%). Exploitation of malonate chemistry, as well as recycling of the unhydrolyzed isomer from the enantioselective hydrolysis, has resulted in a process which is both practical and economical. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00330-4

文献信息

• Stereoselective preparation of 2-substituted succinic acid derivatives
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US05808085A1

  公开（公告）日：1998-09-15

  A highly efficient and practical means has been developed which enables compounds of the formula: ##STR1## wherein R.sup.1 is lower alkoxy, lower alkylamino, di-(loweralkyl) amino, or the monovalent radical A--NR.sup.3, wherein A is lower alkyl or A is R.sup.4 R.sup.5 NC(O)CH.sub.2 wherein, for example, R.sup.4 is hydrogen or alkyl and R.sup.5 is hydrogen, alkyl or a substituted alkyl, or R.sup.5 is R.sup.6 R.sup.7 N-Alk wherein R.sup.6 and R.sup.7 each is hydrogen or lower alkyl and Alk is a divalent alkyl radical; R.sup.3 is, for example, benzyl, alkyl or a substituted alkyl; and R.sup.2 is, inter alia, alkyl, cycloalkyl, 1H-imidazol-4-yl, 4-thiazolyl or 2-amino-4-thiazolyl; to be prepared through the kinetic resolution of a compound of the formula: ##STR2## wherein R.sup.1 is as defined herein, R.sup.2 is as defined herein, and B is lower alkyl. These compounds are useful intermediates in the synthesis of renin inhibiting compounds.

  已经开发出一种高效实用的方法，可以使得符合以下式的化合物得以制备：##STR1## 其中R.sup.1是较低的烷氧基、较低的烷基氨基、二-(较低烷基)氨基，或单价基团A--NR.sup.3，其中A是较低的烷基或A是R.sup.4 R.sup.5 NC(O)CH.sub.2，其中，例如，R.sup.4是氢或烷基，R.sup.5是氢、烷基或取代烷基，或R.sup.5是R.sup.6 R.sup.7 N-Alk，其中R.sup.6和R.sup.7各自是氢或较低的烷基，Alk是二价烷基基团；R.sup.3是，例如，苄基、烷基或取代烷基；R.sup.2是，例如，烷基、环烷基、1H-咪唑-4-基、4-噻唑基或2-氨基-4-噻唑基；通过对以下式的化合物进行动力学分辨制备：##STR2## 其中R.sup.1如本文所定义，R.sup.2如本文所定义，B是较低的烷基。这些化合物在合成抑制肾素的化合物中是有用的中间体。
• STEREOSELECTIVE PREPARATION OF 2-SUBSTITUTED SUCCINIC DERIVATIVES
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP0882138B1

  公开（公告）日：2000-07-05
• US5808085A
  申请人：——

  公开号：US5808085A

  公开（公告）日：1998-09-15
• Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives
  作者：Murray D. Bailey、Ted Halmos、Dan Adamson、Josée Bordeleau、Chantal Grand-Maı̂tre

  DOI：10.1016/s0957-4166(99)00330-4

  日期：1999.8

  Prochiral discrimination by the biocatalyst Alcalase(R), an enzyme preparation of subtilisin Carlsberg, was used to effect enantio- and regioselective monohydrolysis of a variety of(RS)-2-substituted succinate diesters to afford the corresponding half esters in modest to excellent enantiomeric excesses (>99%). Exploitation of malonate chemistry, as well as recycling of the unhydrolyzed isomer from the enantioselective hydrolysis, has resulted in a process which is both practical and economical. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.