5-cyclohexylpent-4-yn-1-ol | 195535-08-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-cyclohexylpent-4-yn-1-ol
• CAS: 195535-08-1
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: OEPRYCGLMUASSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  278.3±19.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  5-cyclohexylpent-4-yn-1-ol 在 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(5-Cyclohexyl-1-vinyl-pent-4-ynyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Enynes Catalyzed by an Organoyttrium Complex

  摘要：

  The organoyttrium complex Cp*2YCH3.THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of 1,6- and 1,7-enynes.. The catalyst's ability to insert the alkyne in preference to the alkene in a regioselective manner, combined with the high diastereoselectivity of the insertion process, yields a product with only one stereochemistry about the exocyclic olefin. The reaction proceeds under extremely mild conditions with short reaction times. Cyclization of enynes functionalized in the allylic position affords silylated carbocycles with high diastereoselectivities and excellent yields.

  DOI：

  10.1021/ja971538g
• 作为产物：
  描述：

  三环己基硼烷 在 sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 双氧水 、 碘 作用下， 以 四氢呋喃 为溶剂， 生成 5-cyclohexylpent-4-yn-1-ol
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Enynes Catalyzed by an Organoyttrium Complex

  摘要：

  The organoyttrium complex Cp*2YCH3.THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of 1,6- and 1,7-enynes.. The catalyst's ability to insert the alkyne in preference to the alkene in a regioselective manner, combined with the high diastereoselectivity of the insertion process, yields a product with only one stereochemistry about the exocyclic olefin. The reaction proceeds under extremely mild conditions with short reaction times. Cyclization of enynes functionalized in the allylic position affords silylated carbocycles with high diastereoselectivities and excellent yields.

  DOI：

  10.1021/ja971538g

文献信息

• Remote Functionalization by Pd-Catalyzed Isomerization of Alkynyl Alcohols
  作者：Simone Scaringi、Baptiste Leforestier、Clément Mazet

  DOI：10.1021/jacs.4c05136

  日期：2024.7.10

  remote functionalizations based on alkene isomerization. In contrast, protocols based on alkyne isomerization are comparatively rare. Herein, we report a general Pd-catalyzed long-range isomerization of alkynyl alcohols. Starting from aryl-, heteroaryl-, or alkyl-substituted precursors, the optimized system provides access preferentially to the thermodynamically more stable α,β-unsaturated aldehydes

  近年来，基于烯烃异构化的远程官能化催化方法的开发取得了进展。相比之下，基于炔烃异构化的方案相对较少。在此，我们报道了一种通用的 Pd 催化的炔醇长程异构化方法。从芳基、杂芳基或烷基取代的前体开始，优化的系统优先提供热力学更稳定的α,β-不饱和醛，并且与潜在敏感的官能团相容。我们表明，碳-碳三键的两个 π 组分的迁移可以在几个亚甲基单元上持续。计算研究有助于阐明负责反应性和选择性的关键基本步骤。其中包括在最终互变异构事件中非正统的膦辅助去质子化而不是更传统的β-氢化物消除。