tert-Butyl 2-<(tert-Butylsulfonyl)oxy>-2(Z)-nonenoate | 138336-41-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: tert-Butyl 2-<(tert-Butylsulfonyl)oxy>-2(Z)-nonenoate
• CAS: 138336-41-1
• 化学式: C₁₇H₃₂O₄S
• 分子量: 332.505
• InChiKey: KTNABGHSYGUWJE-YPKPFQOOSA-N

物化性质

• 沸点：
  449.2±28.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl 2-<(tert-Butylsulfonyl)oxy>-2(Z)-nonenoate 在 sodium dithionite 、 甲基三辛基氯化铵 、 碳酸氢钠 作用下， 以 环己烷 、 水 为溶剂， 反应 1.0h， 以25%的产率得到tert-Butyl 2(E)-Nonenoate
  参考文献：
  名称：

  A new way toward Z.alpha.,.beta. unsaturated esters: a pyrethroid application

  摘要：

  Use of the stereospecific condensation of beta-carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare Z alpha,beta unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HSO2-, followed by an anti elimination of SO2 and the sulfinate group. This method discovered in the pyrethroid series for the synthesis of acrinathrin 1 could have general application.

  DOI：

  10.1021/jo00028a034
• 作为产物：
  描述：

  tert-butyl 2-(tert-butylthio)acetate 在 甲基磺酰氯 、 三乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 62.5h， 生成 tert-Butyl 2-<(tert-Butylsulfonyl)oxy>-2(Z)-nonenoate
  参考文献：
  名称：

  A new way toward Z.alpha.,.beta. unsaturated esters: a pyrethroid application

  摘要：

  Use of the stereospecific condensation of beta-carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare Z alpha,beta unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HSO2-, followed by an anti elimination of SO2 and the sulfinate group. This method discovered in the pyrethroid series for the synthesis of acrinathrin 1 could have general application.

  DOI：

  10.1021/jo00028a034