2-(prop-2-yn-1-yl)cyclohexan-1-ol | 1198229-45-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(prop-2-yn-1-yl)cyclohexan-1-ol
• 英文别名: trans-2-Propargyl-cyclohexanol；(1S,2R)-2-prop-2-ynylcyclohexan-1-ol
• CAS: 1198229-45-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: HSTZTEDWURGETC-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  2-(prop-2-yn-1-yl)cyclohexan-1-ol 在 copper(l) iodide 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 trans-1-oxadecal-2-one
  参考文献：
  名称：

  从炔醇合成γ-和δ-内酯

  摘要：

  炔基苯基硒化物与对甲苯磺酸的反应引起质子诱导的闭环反应，得到 γ-和 5-内酯。

  DOI：

  10.1055/s-2006-932477

文献信息

• Bismuth(<scp>iii</scp>)-catalyzed bis-cyclization of propargylic diol-esters: a unified approach for the synthesis of [5,5]- and [6,5]-oxaspirolactones
  作者：Digambar A. Kambale、Balasaheb R. Borade、Ravindar Kontham

  DOI：10.1039/d1ob00974e

  日期：——

  Herein we disclose an unprecedented intramolecular cascade strategy for the construction of α,β-unsaturated [5,5]- and [6,5]-oxaspirolactones that capitalizes on the π-electrophilic Lewis acid-catalyzed 5-exo-dig or 6-exo-dig mode of cyclization of propargylic diol esters, followed by dehydration and spirolactonization steps. Moreover, semi-protected substrates also delivered the respective oxaspirolactones

  在此，我们公开了一种前所未有的分子内级联策略，用于构建 α,β-不饱和 [5,5]- 和 [6,5]-氧杂螺内酯，该策略利用 π-亲电子路易斯酸催化的 5 -exo-dig或 6-炔丙基二醇酯环化的exo-dig模式，然后是脱水和螺内酯化步骤。此外，半保护底物还可以在最佳反应条件下以相同的容易程度和可观的收率递送各自的氧杂螺内酯。
• Thorpe–Ingold effect in copper(II)-catalyzed formal hydroalkoxylation–hydroarylation reaction of alkynols with indoles
  作者：Nitin T. Patil、Vivek S. Raut、Rahul D. Kavthe、Vaddu V.N. Reddy、P.V.K. Raju

  DOI：10.1016/j.tetlet.2009.09.057

  日期：2009.11

  The use of Cu(OTf)(2) as a catalyst for tandem hydroalkoxylation-hydroarylation reaction of alkynes tethered with hydroxyl group is reported. The reaction proceeds at 60 degrees C or even at room temperature with 5 mol% catalyst loading and produces C-3-substituted indoles in good to high yields. The method was shown to be applicable to a broad range of indoles, containing electron-withdrawing and electron-donating substituents, and alkynol substrates bearing sterically demanding substituents in the tether. Interestingly, it was found that Thorpe-Ingold effect is operating for this cyclization reaction. Easy availability and low cost of Cu(OTf)(2) make this method attractive and amenable for large-scale synthesis compared to known literature methods. (C) 2009 Published by Elsevier Ltd