2-(2-bromo-2-propenyl)-2-(methoxycarbonyl)-1,4-butanedioic acid 4-(1,1-dimethyl-ethyl) 1-methyl ester | 192516-41-9

• 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: 2-(2-bromo-2-propenyl)-2-(methoxycarbonyl)-1,4-butanedioic acid 4-(1,1-dimethyl-ethyl) 1-methyl ester
• 英文别名: 2-(2-Bromo-2-propenyl)-2-(methoxycarbonyl)-1,4-butanedioic Acid 4-(1,1-Dimethylethyl) 1-Methyl Ester；1-O-tert-butyl 2-O,2-O-dimethyl 4-bromopent-4-ene-1,2,2-tricarboxylate
• CAS: 192516-41-9
• 化学式: C₁₄H₂₁BrO₆
• 分子量: 365.221
• InChiKey: PAEVMXDAEQYWTK-UHFFFAOYSA-N

物化性质

• 沸点：
  379.4±42.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-2-propenyl)-2-(methoxycarbonyl)-1,4-butanedioic acid 4-(1,1-dimethyl-ethyl) 1-methyl ester 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以45%的产率得到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
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 dimethyl 2-(2'-bromoallyl)malonate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以92%的产率得到2-(2-bromo-2-propenyl)-2-(methoxycarbonyl)-1,4-butanedioic acid 4-(1,1-dimethyl-ethyl) 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：EP0882138A1

  公开（公告）日：1998-12-09
• US5808085A
  申请人：——

  公开号：US5808085A

  公开（公告）日：1998-09-15
• [EN] STEREOSELECTIVE PREPARATION OF 2-SUBSTITUTED SUCCINIC DERIVATIVES<br/>[FR] PREPARATION STEREOSELECTIVE DE DERIVES DE L'ACIDE SUCCINIQUE SUBSTITUE EN POSITION 2
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD./BOEHRINGER INGELHEIM (CANADA) LTÉE

  公开号：WO1997023641A1

  公开（公告）日：1997-07-03

  (EN) A process for the preparation of compounds of formula (II) wherein R1 is lower alkoxy, lower alkylamino, di-(loweralkyl)amino, or the monovalent radical A-NR3, wherein A is lower alkyl or A is R4R5NC(O)CH2 wherein, for example, R4 is hydrogen or alkyl and R5 is hydrogen, alkyl or a substituted alkyl, or R5 is R6R7N-Alk wherein R6 and R7 each is hydrogen or lower alkyl and Alk is a divalent alkyl radical; R3 is, for example, benzyl, alkyl or a substituted alkyl; and R2 is, inter alia, alkyl, cycloalkyl, 1H-imidazol-4-yl, 4-thiazolyl or 2-amino-4-thiazolyl; through the kinetic resolution of a compound of formula (III) wherein R1 is as defined herein, R2 is as defined herein, and B is lower alkyl. These compounds are useful intermediates in the synthesis of renin inhibiting compounds.(FR) L'invention concerne un procédé de préparation des composés de la formule (II). Dans cette formule, R1 est alcoxy inférieur, alkylamino inférieur, di-(alkyl inférieur)amino ou le radical monovalent A-NR3, où A est alkyle inférieur ou A est R4R5NC(O)CH2, où par exemple R4 est hydrogène ou alkyle et R5 est hydrogène, alkyle ou alkyle substitué, ou R5 est R6R7N-Alk où R6 et R7 sont chacun un hydrogène ou un alkyle inférieur ou un alkyle substitué et Alk est un radical alkyle divalent; R3 est par exemple, benzyle ou alkyle substitué; et R2 est, entre autres, alkyle, cycloalkyle, 1H-imidazol-4-yle, 4-thiazolyle ou 2-amino-4-thiazolyle. Cette préparation est une résolution par cinétique de réaction d'un composé de la formule (III), dans laquelle R1 est comme défini ci-dessus, R2 est comme défini ci-dessus et B est un alkyle inférieur. Ces composés sont d'utiles intermédiaires pour la synthèse de composés inhibiteurs de la rénine.
• 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.