4-ethyl-1-methyl 2-bromo-2-methylsuccinate

• 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: 4-ethyl-1-methyl 2-bromo-2-methylsuccinate
• 英文别名: 2-Methyl-2-bromosuccinic acid, 2-methyl, 4-ethyl ester；4-O-ethyl 1-O-methyl 2-bromo-2-methylbutanedioate
• 化学式: C₈H₁₃BrO₄
• 分子量: 253.093
• InChiKey: AFTBFEFJBPGFNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-ethyl-1-methyl 2-methylsuccinate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 以67%的产率得到4-ethyl-1-methyl 2-bromo-2-methylsuccinate
  参考文献：
  名称：

  Mechanism of electron impact ionization-induced halogen elimination from 2-methyl-2-bromosuccinates

  摘要：

  AbstractThe electron impact‐induced halogen elimination from 2‐methyl‐2‐bromosuccinates occurs only in the one of the two isomeric methyl ethyl esters in which the ethoxycarbonyl group is remote from the halogen, in analogy with the corresponding previously reported halosuccinates. However, the occurrence of debromination in dimethyl 2‐methyl‐2‐bromosuccinate contrasts with the behaviour of dimethyl bromosuccinate, indicating different mechanisms for this process in the two systems. Collision‐induced dissociation (CID) and deuterium labelling studies led to the conclusion that a hydrogen transfer from the 2‐methyl group to a carbonyl precedes the elimination of Br˙ from dimethyl 2‐methyl‐2‐bromosuccinate, resulting in a protonated dimethyl itaconate structure for the [M – Br]+ ion. An analogous process is the major route leading to [M – Br]+ ion from 1‐methyl‐4‐ethyl 2‐methyl‐2‐bromosuccinate. In this case deuterium labelling and CID measurements indicated a significant contribution of methyl ethyl citraconate and possibly mesaconate owing to partial operation of a mechanism similar to that reported for 1‐methyl‐4‐ethyl 2‐bromosuccinate.

  DOI：

  10.1002/oms.1210280315

文献信息

• Mechanism of electron impact ionization-induced halogen elimination from 2-methyl-2-bromosuccinates
  作者：D. Bornstein、A. Mandelbaum、I. Vidavsky、B. Domon、D. R. Mueller、W. J. Richter

  DOI：10.1002/oms.1210280315

  日期：1993.3

  AbstractThe electron impact‐induced halogen elimination from 2‐methyl‐2‐bromosuccinates occurs only in the one of the two isomeric methyl ethyl esters in which the ethoxycarbonyl group is remote from the halogen, in analogy with the corresponding previously reported halosuccinates. However, the occurrence of debromination in dimethyl 2‐methyl‐2‐bromosuccinate contrasts with the behaviour of dimethyl bromosuccinate, indicating different mechanisms for this process in the two systems. Collision‐induced dissociation (CID) and deuterium labelling studies led to the conclusion that a hydrogen transfer from the 2‐methyl group to a carbonyl precedes the elimination of Br˙ from dimethyl 2‐methyl‐2‐bromosuccinate, resulting in a protonated dimethyl itaconate structure for the [M – Br]+ ion. An analogous process is the major route leading to [M – Br]+ ion from 1‐methyl‐4‐ethyl 2‐methyl‐2‐bromosuccinate. In this case deuterium labelling and CID measurements indicated a significant contribution of methyl ethyl citraconate and possibly mesaconate owing to partial operation of a mechanism similar to that reported for 1‐methyl‐4‐ethyl 2‐bromosuccinate.