(Z)-1-bromo-1-methyl-3-tosyl-1-propene | 136908-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1-bromo-1-methyl-3-tosyl-1-propene
• 英文别名: 1-((E)-3-Bromo-but-2-ene-1-sulfonyl)-4-methyl-benzene；(Z,E)-1-bromo-1-methyl-3-tosyl-1-propene
• CAS: 136908-54-8；136908-61-7
• 化学式: C₁₁H₁₃BrO₂S
• 分子量: 289.193
• InChiKey: VSNDZJYOZRLDKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (erythro/threo)-2,3-dibromo-1-tosylbutane 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以79%的产率得到(Z)-1-bromo-1-methyl-3-tosyl-1-propene
  参考文献：
  名称：

  A simple method for the synthesis of γ-functionalized vinyl and allyl sulfones

  摘要：

  The synthesis of gamma-functionalized vinyl sulfones 3 have been carried out directly starting from dibromides 2 derived from allyl sulfones 1 by reaction with different nucleophiles. The process is stereoselective affording compounds 3 with E configuration except in the case of methallylic derivatives. The regioisomeric gamma-functionalized allyl sulfones 4 were obtained from dibromides 2 or from vinyl sulfones 3, with Z configuration, except when triphenylphosphine was used as nucleophile, in this case the corresponding (E)-vinylphosphonium bromide 4al was obtained.

  DOI：

  10.1016/s0040-4020(01)86563-7

文献信息

• A simple method for the synthesis of γ-functionalized vinyl and allyl sulfones
  作者：Carmen Nájera、Alfonso Pérez-Pinar、JoséM. Sansano

  DOI：10.1016/s0040-4020(01)86563-7

  日期：1991.8

  The synthesis of gamma-functionalized vinyl sulfones 3 have been carried out directly starting from dibromides 2 derived from allyl sulfones 1 by reaction with different nucleophiles. The process is stereoselective affording compounds 3 with E configuration except in the case of methallylic derivatives. The regioisomeric gamma-functionalized allyl sulfones 4 were obtained from dibromides 2 or from vinyl sulfones 3, with Z configuration, except when triphenylphosphine was used as nucleophile, in this case the corresponding (E)-vinylphosphonium bromide 4al was obtained.