1-cyclopropyl-4-methyl-3-trimethylsilyloxypentane-1-one | 127934-21-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-cyclopropyl-4-methyl-3-trimethylsilyloxypentane-1-one
• 英文别名: 1-cyclopropyl-4-methyl-3-trimethylsilyloxypentan-1-one
• CAS: 127934-21-8
• 化学式: C₁₂H₂₄O₂Si
• 分子量: 228.407
• InChiKey: PWCRBWGPOLFDRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-4-methyl-3-trimethylsilyloxypentane-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 以97%的产率得到1-cyclopropyl-4-methyl-2E-penten-1-one
  参考文献：
  名称：

  Simple synthesis of?-silyloxyacylcyclopropanes and the homoallyl rearrangement of cyclopropylcarbinols by the action of trimethylsilyl halides in the presence of zinc halides

  摘要：

  The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave beta-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones. Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides. The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.

  DOI：

  10.1007/bf00958248
• 作为产物：
  描述：

  1-环丙基-1-(三甲基硅烷基氧基)-乙烯 、 异丁醛 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到1-cyclopropyl-4-methyl-3-trimethylsilyloxypentane-1-one
  参考文献：
  名称：

  Simple synthesis of?-silyloxyacylcyclopropanes and the homoallyl rearrangement of cyclopropylcarbinols by the action of trimethylsilyl halides in the presence of zinc halides

  摘要：

  The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave beta-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones. Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides. The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.

  DOI：

  10.1007/bf00958248

文献信息

• Synthesis of ?-silyloxyacylcyclopropanes catalyzed by zinc salts and the homoallylic rearrangement of cyclopropylcarbinols by the action of trimethylsilyl halides
  作者：N. M. Ivanova、B. A. Cheskis、A. M. Moiseenkov、O. M. Nefedov

  DOI：10.1007/bf00963040

  日期：1990.1
• IVANOVA, N. M.;CHEEKIS, B. A.;MOISEENKO, A. M.;NEFEDOV, O. M., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 225-236
  作者：IVANOVA, N. M.、CHEEKIS, B. A.、MOISEENKO, A. M.、NEFEDOV, O. M.

  DOI：——

  日期：——
• CHESKIS, B. A.;IVANOVA, N. M.;MOISEENKOV, A. M.;NEFEDOV, O. M., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2025-2036
  作者：CHESKIS, B. A.、IVANOVA, N. M.、MOISEENKOV, A. M.、NEFEDOV, O. M.

  DOI：——

  日期：——
• Simple synthesis of?-silyloxyacylcyclopropanes and the homoallyl rearrangement of cyclopropylcarbinols by the action of trimethylsilyl halides in the presence of zinc halides
  作者：B. A. Cheskis、N. M. Ivanova、A. M. Moiseenkov、O. M. Nefedov

  DOI：10.1007/bf00958248

  日期：1990.9

  The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave beta-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones. Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides. The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.