cyclohexyl(cyclopentyl)methanol | 872267-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl(cyclopentyl)methanol
• 英文别名: Cyclopentyl-cyclohexyl-carbinol
• CAS: 872267-21-5
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: IQCGDXUMNIZNDB-UHFFFAOYSA-N

物化性质

• 沸点：
  274.4±8.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  cyclohexyl(cyclopentyl)methanol 在 铬 、 溶剂黄146 作用下， 生成 甲酮,环己基并环戊基-
  参考文献：
  名称：

  Vavon; Mitchovitch, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1928, vol. 186, p. 703

  摘要：

  DOI：
• 作为产物：
  描述：

  甲酮,环己基并环戊基- 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以62 mg的产率得到cyclohexyl(cyclopentyl)methanol
  参考文献：
  名称：

  通过CN键裂解，镍催化烷基羧酸衍生物与吡啶鎓盐的交叉偶联。

  摘要：

  羧酸衍生物和烷基吡啶鎓盐通过C–N键断裂的亲电-亲电交叉偶联得到了发展。该方法以其简单性而著称，可指导我们选择各种功能化的酮，产率高至优异。除酰氯外，羧酸还用作酰化剂，这使我们能够结合酸敏感性官能团，例如MOM，BOC和乙缩醛。使用TEMPO进行的对照实验揭示了一个基本途径。

  DOI：

  10.1021/acs.orglett.0c00554

文献信息

• Bedos, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1923, vol. 177, p. 959
  作者：Bedos

  DOI：——

  日期：——
• Construction of Cyclopentyl Carbinols from ω-Tosyloxy-1-alkenyl Boronate Esters and Grignard Reagents
  作者：Yuichi Kobayashi、Moriteru Asano、Yohei Kiyotsuka

  DOI：10.3987/com-08-s(f)69

  日期：——

  Addition of RMgCl (R = n-Bu, Ph) to pinacol esters of 6-tosyloxy-1-alkenyl boronic acids at -78 degrees C gave the borates, which upon warming to room temperature underwent migration of R on boron to C(l) carbon and concomitant ring construction C-C bond formation between C(2) and C(6), eventually producing cyclopentyl alkyl (or aryl) carbinols after oxidative workup of the borane intermediates with 35% H2O2. Eight examples are presented and the reaction was applied to construction of a cyclohexyl carbinol.
• Bedos, Bulletin de la Societe Chimique de France, 1926, vol. <4> 39, p. 480,485
  作者：Bedos

  DOI：——

  日期：——
• Investigation of Cyclization Reactions of Dicyclohexyl-6-iodo- and -6-tosylhexenylborane. A Facile Radical Cyclization Diverted to a Rearrangement−Cyclization with Base
  作者：Diane M. Hinkens、M. Mark Midland

  DOI：10.1021/jo900243q

  日期：2009.6.5

  Dicyclohexyl-6-iodohexenylborane efficiently undergoes radical cyclization at room temperature using tri-n-butyltin hydride as a hydrogen donor and without the aide of a radical initiator. Efforts to develop environmentally friendly reagents using hypophosphites as substitutes for tin hydrides in this reaction provided a 60% yield of cyclopentanemethanol when tetrabutylammonium hypophosphite was used. Air was necessary as an initiator when hypophosphites were used. During investigations of the radical cyclization reactions, it was discovered that excess tetrabutyl ammonium hydroxide provided the rearrangement-cyclization product in excellent yield. Since this product was chiral, efforts were focused on achieving enantioselectivity. Oxazaborolidines made from chiral amino alcohols and 6-tosy-1-hexenylboronic acid were treated with methyllithium to give 1-cyclopentylethanol after oxidation in 60% ee, demonstrating that oxazaborolidines were effective chiral directors for this reaction.