环丙甲醇,a-癸基- | 139489-32-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 环丙甲醇,a-癸基-
• 英文名称: 1-cyclopropylundecan-1-ol
• CAS: 139489-32-0
• 化学式: C₁₄H₂₈O
• 分子量: 212.376
• InChiKey: ASQFRWQYWCZFGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  274.1±8.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  环丙甲醇,a-癸基- 在 三甲基溴硅烷 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以92%的产率得到1-bromo-tetradec-(3E)-en
  参考文献：
  名称：

  Synthesis of 3E-tetradecenol, 3E, 9E-tetradecadienol, and their acetates starting from acetylcyclopropane

  摘要：

  Stereospecific synthesis of the linear E-olefins mentioned in the title was realized by a general scheme that was worked out earlier by the authors and which includes as key steps homologization of the corresponding aliphatic pentakisnoraldehydes by means of trimethylsilyloxyvinylcyclopropane and ZnBr2-initiated rearrangement of the intermediate cyclopropylcarbinols under the influence of Me3SiBr.

  DOI：

  10.1007/bf00957995
• 作为产物：
  描述：

  1-环丙基-1-(三甲基硅烷基氧基)-乙烯 在 镍 sodium tetrahydroborate 、 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 10.25h， 生成 环丙甲醇,a-癸基-
  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

• Rapid Access to Arylated and Allylated Cyclopropanes <i>via</i> Brønsted Acid-Catalyzed Dehydrative Coupling of Cyclopropylcarbinols
  作者：Naveen Yadav、Jabir Khan、Aparna Tyagi、Sanjay Singh、Chinmoy Kumar Hazra

  DOI：10.1021/acs.joc.2c00690

  日期：2022.5.20

  A regioselective protocol for the synthesis of cyclopropyl derivatives that relies on Brookhart acid-catalyzed dehydrative coupling over substituted cyclopropylcarbinols without rearrangement is reported herein. The reactions proceed promptly at 25 °C with only 2.0 mol % catalyst loading and produce the cyclopropyl derivatives in excellent yields. This method is well tolerated with a vast range of

  本文报道了一种用于合成环丙基衍生物的区域选择性方案，该方案依赖于 Brookhart 酸催化的在取代的环丙基甲醇上的脱水偶联而不发生重排。反应在 25 °C 下迅速进行，催化剂负载量仅为 2.0 mol%，并以优异的收率产生环丙基衍生物。这种方法对包括脂肪族环丙醇在内的多种环丙醇具有良好的耐受性，其中没有获得消除产物，证明了该协议的实用性。此外，Hammett 相关性表明形成环丙基羰基阳离子，然后发生偶联反应。一个非常有效的克级反应也已被证明具有高周转数。
• Brookhart's Acid‐Catalyzed Switchable Regioselective <i>N</i> ‐Alkylation of Arylamines/Heterocyclic Amines with Cyclopropylcarbinols by Temperature Regulation
  作者：Naveen Yadav、Aparna Tyagi、Jabir Khan、Chinmoy Kumar Hazra

  DOI：10.1002/chem.202201938

  日期：2022.11.16

  regioselective divergent approach for N-alkylation of arylamines and heterocyclic amines by utilising cyclopropylcarbinols is presented herein. The reaction offers N-alkylated cyclopropyl derivatives and homoallyl amines by employing 2.5 mol% catalyst loading at different temperatures in excellent regioselectivity and yields. Several control experiments and spectroscopic studies have been performed to gain insight

  本文介绍了一种前所未有的 Brookhart 酸催化温度可切换区域选择性发散方法，用于通过使用环丙基甲醇对芳基胺和杂环胺进行N-烷基化。该反应通过在不同温度下使用 2.5 mol% 的催化剂负载量提供N-烷基化环丙基衍生物和高烯丙基胺，具有出色的区域选择性和产率。已经进行了一些控制实验和光谱研究以深入了解反应机制。
• Sukkari, Hanadi El; Renoux, Brigitte; Bertrand, Philippe, Journal of Chemical Research, Miniprint, 1999, # 8, p. 2157 - 2178
  作者：Sukkari, Hanadi El、Renoux, Brigitte、Bertrand, Philippe、Gesson, Jean-Pierre

  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：——
• IVANOVA, N. M.;CHESKIS, B. A.;RUBANOVA, E. V.;YATSYNIN, V. G.;MOISEENKOV,+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 640-644
  作者：IVANOVA, N. M.、CHESKIS, B. A.、RUBANOVA, E. V.、YATSYNIN, V. G.、MOISEENKOV,+

  DOI：——

  日期：——