(E)-1-cyclopropylundec-2-en-1-one | 132119-94-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-cyclopropylundec-2-en-1-one
• 英文别名: 1-cyclopropyl-2E-undecen-1-one
• CAS: 132119-94-9
• 化学式: C₁₄H₂₄O
• 分子量: 208.344
• InChiKey: GVSPDWMDTGYXJT-MDZDMXLPSA-N

物化性质

• 沸点：
  84-85 °C(Press: 0.03 Torr)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  15.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-1-cyclopropylundec-2-en-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 三甲基溴硅烷 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 1-bromo-3E,5E-tetradecadiene
  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：

  N-(1-cyclopropylethylidene)-cyclohexanamine 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.33h， 生成 (E)-1-cyclopropylundec-2-en-1-one
  参考文献：
  名称：

  Moiseenkov, Alexander M.; Czeskis, Boris A.; Ivanova, Natalya M., Journal of the Chemical Society. Perkin transactions I, 1991, p. 2639 - 2649

  摘要：

  DOI：

文献信息

• Simple synthesis of acetogenin transoid insect pheromones starting from acetylcyclopropane
  作者：B. A. Cheskis、N. M. Ivanova、A. M. Moiseenkov、O. M. Nefedov

  DOI：10.1007/bf00961235

  日期：1991.7

  A highly effective synthesis of a series of alkyl and 1-alkenyl cyclopropyl ketones, which are key components in the complete synthesis of a large number of transoid lepidoptera pheromones, has been developed, based on the alkylation of N-cyclohexyl-1-cyclopropylethylideneimine or its condensation with aldehydes.
• 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：——
• MOISEENKOV, ALEXANDER M.;CZESKIS, BORIS A.;IVANOVA, NATALYA M.;NEFEDOV, O+, MENDELEEV COMMUN.,(1991) N, C. 13-14
  作者：MOISEENKOV, ALEXANDER M.、CZESKIS, BORIS A.、IVANOVA, NATALYA M.、NEFEDOV, O+

  DOI：——

  日期：——
• CHESKIS, B. A.;IVANOVA, N. M.;MOISEENKOV, A. M.;NEFEDOV, O. M., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1555-1562
  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.