cis-4-benzyloxy-1-vinylcyclohexan-1-ol | 894074-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-4-benzyloxy-1-vinylcyclohexan-1-ol
• CAS: 894074-65-8
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: WRHUULBEDQBYQP-GASCZTMLSA-N

物化性质

• 沸点：
  336.1±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-4-benzyloxy-1-vinylcyclohexan-1-ol 在 diborane(6) 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到cis-4-benzyloxy-1-(2-hydroxyethyl)cyclohexan-1-ol
  参考文献：
  名称：

  Chemo enzymatic synthesis of Rengyol and Isorengyol

  摘要：

  Cyanohydrins 2 of O-protected 4-hydroxycyclohexanones 1 are excellent starting compounds for the synthesis of Isorengyol (I) and Rengyol (II). The cyano group of the O-benzyl derivative 2d is first converted into the corresponding aldehyde 4, which via Wittig olefination led to the vinyl Compound 6. Hydroboration of the trans-derivative (trans-6) leads, after debenzylation, to Isorengyol, whereas hydroboration and debenzylation of the cis-isomer (cis-6) gives Rengyol. With hydroxynitrile lyases (HNLs) as catalysts the stereoselective preparation of cis- as well as trans-cyanohydrin 2d is possible, which enables the selective preparation of Isorengyol or Rengyol, respectively. The trans-con figuration of Isorengyol and the cis-configuration of Rengyol were secured by X-ray crystal structure analysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.012
• 作为产物：
  描述：

  (4-benzyloxy-1-vinylcyclohexyloxy)trimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以45%的产率得到trans-4-benzyloxy-1-vinylcyclohexan-1-ol
  参考文献：
  名称：

  Chemo enzymatic synthesis of Rengyol and Isorengyol

  摘要：

  Cyanohydrins 2 of O-protected 4-hydroxycyclohexanones 1 are excellent starting compounds for the synthesis of Isorengyol (I) and Rengyol (II). The cyano group of the O-benzyl derivative 2d is first converted into the corresponding aldehyde 4, which via Wittig olefination led to the vinyl Compound 6. Hydroboration of the trans-derivative (trans-6) leads, after debenzylation, to Isorengyol, whereas hydroboration and debenzylation of the cis-isomer (cis-6) gives Rengyol. With hydroxynitrile lyases (HNLs) as catalysts the stereoselective preparation of cis- as well as trans-cyanohydrin 2d is possible, which enables the selective preparation of Isorengyol or Rengyol, respectively. The trans-con figuration of Isorengyol and the cis-configuration of Rengyol were secured by X-ray crystal structure analysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.012

文献信息

• Catalytic Radical–Polar Crossover Reactions of Allylic Alcohols
  作者：Eric E. Touney、Nicholas J. Foy、Sergey V. Pronin

  DOI：10.1021/jacs.8b12075

  日期：2018.12.12

  Radical-polar crossover hydrofunctionalizations of tertiary allylic alcohols are described. Depending on the structure of the catalyst, corresponding epoxides or semipinacol rearrangement products are selectively obtained in good yields. Experimental evidence points to the participation of alkylcobalt complexes as electrophilic intermediates.

  描述了叔烯丙醇的自由基极性交叉氢官能化。取决于催化剂的结构，相应的环氧化物或半频哪醇重排产物以良好的产率选择性地获得。实验证据表明烷基钴配合物作为亲电子中间体的参与。