(E)-2-Bromo-but-2-enedioic acid 4-ethyl ester 1-methyl ester | 136880-48-3

• 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: (E)-2-Bromo-but-2-enedioic acid 4-ethyl ester 1-methyl ester
• CAS: 136880-48-3
• 化学式: C₇H₉BrO₄
• 分子量: 237.05
• InChiKey: HMOVEBUUWVGTLP-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-Diazo-succinic acid 4-ethyl ester 1-methyl ester 在 bis(collidine)bromine(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-2-Bromo-but-2-enedioic acid 4-ethyl ester 1-methyl ester 、 (Z)-2-Bromo-but-2-enedioic acid 4-ethyl ester 1-methyl ester
  参考文献：
  名称：

  Reaction of bis(Sym-Collidine)-Bromine(I) Hexafluorophosphate with α-Diazo Esters

  摘要：

  Reaction of alpha-diazo esters with bis(sym-collidine)bromine(I) hexafluorophosphate in methylene chloride at -40 degrees C led to alpha-bromo-alpha,beta-unsaturated esters.

  DOI：

  10.1080/00397919908086009

文献信息

• Behaviour of isomeric methyl ethyl and ethyl methyl halosuccinates under electron impact. Elimination of a halogen atom by a multi-step mechanism
  作者：D. Bornstein、A. Mandelbaum、I. Vidavsky、B. Domon、D. Mueller、W. J. Richter

  DOI：10.1002/oms.1210260917

  日期：1991.9

  AbstractThe electron impact mass spectra of isomeric methyl ethyl and ethyl methyl halosuccinates (X = Cl and Br) are surprisingly different. Only the isomers with the ethyl group remote from the halogen give rise to [M ‐ X]+ ions. A low‐energy collision‐induced dissociation study of deuterium‐labelled analogues of the former isomers indicates that the [M ‐ X]+ ions are mixtures of protonated methyl ethyl maleate (major component, > 85%) and fumarate, and the loss of the halogen atom is a multi‐step process including at least two specific hydrogen transfers. Migration of a β‐hydrogen atom to the carbonyl oxygen within the ethoxycarbouyl group produces a primary radical site in a distonic intermediate which, by subsequent abstraction of a hydrogen atom from C(3), triggers the ejection of X from C(2) with concomitant double bond formation. Whereas in the other isomer an [M ‐ X]+ ion is absent or negligible, a characteristic double loss of C2H4 and CO2 is observed.