1-cyclopropylnonan-1-one | 59533-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclopropylnonan-1-one
• CAS: 59533-58-3
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: MDAHIDZFTKTAIH-UHFFFAOYSA-N

物化性质

• 沸点：
  74 °C(Press: 1 Torr)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-cyclopropylnonan-1-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-cyclopropylnonan-1-ol
  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 在 镍 氢气 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 6.33h， 生成 1-cyclopropylnonan-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

• Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg‐Exchange Reaction Using <i>s</i> Bu ₂ Mg in Toluene
  作者：Alisa S. Sunagatullina、Ferdinand H. Lutter、Paul Knochel

  DOI：10.1002/anie.202116625

  日期：2022.3.21

  secondary dialkylmagnesium reagents were prepared in toluene by the reaction of sBu2Mg with alkyl iodides (25–40 °C, 1–4 h). Stereoconvergent I/Mg-exchanges were observed for secondary cyclohexyl iodides leading after quenching reactions to products with high enantio- and diastereoselectivity, including homo-aldol products. Mechanistic studies confirmed radical pathways for these exchanges.

  伯二烷基镁试剂和仲二烷基镁试剂是通过s Bu 2 Mg 与烷基碘反应在甲苯中制备的（25–40 °C，1–4 小时）。观察到仲环己基碘的立体会聚 I/Mg 交换导致猝灭反应后产生具有高对映选择性和非对映选择性的产物，包括同羟醛产物。机制研究证实了这些交换的根本途径。
• 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.
• Moiseenkov, Alexander M.; Czeskis, Boris A.; Ivanova, Natalya M., Journal of the Chemical Society. Perkin transactions I, 1991, p. 2639 - 2649
  作者：Moiseenkov, Alexander M.、Czeskis, Boris A.、Ivanova, Natalya M.、Nefedov, Oleg M.

  DOI：——

  日期：——
• Myrsina,R.A.; Kuznetsov,N.V., Soviet progress in chemistry, 1976, vol. 42, # 4, p. 70 - 73
  作者：Myrsina,R.A.、Kuznetsov,N.V.

  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：——