1-allyl-2-(prop-2-yn-1-yl)cyclohexanol | 109433-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-allyl-2-(prop-2-yn-1-yl)cyclohexanol
• 英文别名: 1-(Prop-2-en-1-yl)-2-(prop-2-yn-1-yl)cyclohexan-1-ol；1-prop-2-enyl-2-prop-2-ynylcyclohexan-1-ol
• CAS: 109433-08-1
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: LPXLWDBPWQMJHE-UHFFFAOYSA-N

物化性质

• 沸点：
  245.8±13.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-allyl-2-(prop-2-yn-1-yl)cyclohexanol 在 六羰基钨 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以96%的产率得到(+/-)-(3aR,7aS)-7a-allyl-2,3,3a,4,5,6,7,7a-octahydro-2-methylenebenzofuran
  参考文献：
  名称：

  [W（CO）5]催化的1，1-二取代的4-戊炔-1-醇的内-或外-环异构化反应：实验和理论研究。

  摘要：

  从实验和理论的角度研究了[W（CO）5]催化的1，1-二取代的4-戊炔-1-醇衍生物的环异构化反应。已经评估了三种不同的催化体系{预制的[（thf）W（CO）5]，[W（CO）6] /过量的Et3N和[W（CO）6] / 2 mol％Et3N]。我们已经发现，根据所用的Et 3 N的量和沿起始炔醇的烷基链的取代，反应进行以给出正式的内-或外-环异构化产物。理论研究使我们能够找到反应的机理，这些反应解释了形式的内-或外-环异构化产物的形成。

  DOI：

  10.1002/chem.200500537

文献信息

• Chemoenzymatic route to optically active dihydroxy cyclopenta[b]naphthalenones; precursors for decalin-based bioactive natural products
  作者：Devrim Özdemirhan、Özlem Sarıçelik

  DOI：10.1016/j.tetasy.2016.11.010

  日期：2017.1

  The development of an efficient chemoenzymatic route for the synthesis of optically active dihydroxy cyclopenta[b]naphthalenones; (+)-1,4a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cyclopenta[b]naphthalen-2(4H)-one (+)-10 and (+)-1,8a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cydopenta[b]naphthalen-2(4H)-one (+)-11 is described. Different lipases and esterases were tested in the enzymatic hydrolysis of the corresponding acetates (+/-)-4a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-8, (+/-)-8a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-9, CRL (Candida Rugosa Lipase) and PLE (Pig Liver Esterase) were found to be the most effectual enzymes; for (-)-8 by 47% ee with the corresponding dihydroxy; (+)-10 by 98% ee in the presence of CRL; whereas, ()-8 was obtained with 40% ee with the corresponding dihydroxy, (+)-10 with 58% ee in the PLE hydrolysis. It was concluded that CRL was the best biocatalyst for the substrate (+/-)-8. Moreover, enzymatic resolution in the presence of CRL yields, (-)-9 with 46% ee with the corresponding dihydroxy derivative; (+)-11 with 98% ee; however, in the presence of PLE, yields (-)-9 with 36% ee as well as the related dihydroxy derivative; (+)-11 with 49% ee respectively. The study concluded that CRL is the best biocatalyst for compounds (+/-)-8 and (+/-)-9. (C) 2016 Elsevier Ltd. All rights reserved.