Z-1,2-dibromo-3-methyl-1,3-butadiene | 99236-02-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: Z-1,2-dibromo-3-methyl-1,3-butadiene
• 英文别名: Z-1,2-dibromo-3-methylbuta-1,3-diene；1t,2-dibromo-3-methyl-buta-1,3-diene；(Z)-1,2-Dibrom-3-methyl-butadien；1t,2-Dibrom-3-methyl-buta-1,3-dien；1c,2-Dibrom-3-methyl-buta-1,3-dien；(1Z)-1,2-dibromo-3-methylbuta-1,3-diene
• CAS: 99236-02-9
• 化学式: C₅H₆Br₂
• 分子量: 225.911
• InChiKey: NPNZWZMISUESOR-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  Z-1,2-dibromo-3-methyl-1,3-butadiene 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1-溴-3-甲基-3-丁烯-1-炔
  参考文献：
  名称：

  Petrow, Zhurnal Obshchei Khimii, 1943, vol. 13, p. 335

  摘要：

  DOI：
• 作为产物：
  描述：

  1r,2c-Dibrom-3-hydroxy-3-methyl-but-1-en 生成 Z-1,2-dibromo-3-methyl-1,3-butadiene
  参考文献：
  名称：

  Nasarow; Bergel'son, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1540,1543, 1544; engl. Ausg. S. 1614, 1617

  摘要：

  DOI：

文献信息

• Baird, Mark S.; Hussain, Helmi H., Journal of Chemical Research, Miniprint, 1985, # 6, p. 2061 - 2072
  作者：Baird, Mark S.、Hussain, Helmi H.

  DOI：——

  日期：——
• The generation and trapping of 1,2-Dibromo-3-methylbut-2-en-1-ylidenes
  作者：Ahmad R. Al Dulayymi、Juma'a R. Al Dulayymi、Mark S. Baird、Leela Rajaram

  DOI：10.1016/0040-4020(95)00448-h

  日期：1995.7

  1,2-Dibromo-3,3-dimerhylcyclopropene, generated by debromination of 1,1,2,2-tetrabromo-3,3-dimethylcyclopropane on reaction with methyllithium, ring-opens at 0-20 degrees C to produce 1,2-dibromo-3-methylbut-2-en-1-ylidene. This is trapped by alkenes to give vinylcyclopropanes. In the case of electron rich alkenes, the stereochemistry is retained in the product, suggesting that a singlet carbene is involved. In the case of alpha,beta-unsaturated esters, ketones or nitriles, the major cyclopropane produced has the vinyl and electron-withdrawing groups cis-related. 3-(2-Methoxy-ethyl)-3-methyl- and 3-(2-bromoethyl)-3-methyl-1,2-dibromocyclopropenes also ring-open at ambient temperature but little stereoselectivity is observed in the trapping of the derived vinyl-carbenes by alkenes. The reaction of 3-(2-hrdroxrethyl)-3-methyl-1,1,2,2-tetrabromocyclopropane with methyl lithium or diethylphosphite and triethylamine does not lead to an isolable cyclo-propene, but instead to Z-1,2-dibromo-3-methylbuta-1,3-diene; quenching with deuterium oxide at low temperature leads to the incorporation of deuterium at C-1.
• Petrow, Zhurnal Obshchei Khimii, 1943, vol. 13, p. 335
  作者：Petrow

  DOI：——

  日期：——
• Nasarow; Bergel'son, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1540,1543, 1544; engl. Ausg. S. 1614, 1617
  作者：Nasarow、Bergel'son

  DOI：——

  日期：——