[(1S)-1-cyclohexylbut-3-enoxy]methylbenzene | 397251-79-5

• 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: [(1S)-1-cyclohexylbut-3-enoxy]methylbenzene
• CAS: 397251-79-5
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: VOQMSEGZFGBRGG-KRWDZBQOSA-N

物化性质

• 沸点：
  332.2±21.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(1S)-1-cyclohexylbut-3-enoxy]methylbenzene 在 sodium 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 0.85h， 以69%的产率得到(S)-1-cyclohexylbut-3-en-1-ol
  参考文献：
  名称：

  Optically Pure α-(Trimethylsilyl)benzyl Alcohol:  A Practical Chiral Auxiliary for Oxocarbenium Ion Reactions

  摘要：

  GRAPHICSEnantiopure (S)-alpha-(trimethylsilyl)benzyl alcohol (98% ee) was prepared by Noyori's transfer hydrogenation of benzoyltrimethylsilane. The corresponding trimethylsilyl ether was subjected to Marko's silyl modified Sakurai conditions with a variety of aldehydes to afford homoallylic ethers in high diastereoselectivity. The practicality of the alpha-trimethylsilyl benzyl group as an oxocarbenium ion auxiliary was further demonstrated by its efficient deprotection or conversion to a benzyl protecting group.

  DOI：

  10.1021/ol017063m
• 作为产物：
  描述：

  (S)-(-)-α-(Trimethylsilyl)benzenemethanol 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 糖精 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 [(1S)-1-cyclohexylbut-3-enoxy]methylbenzene
  参考文献：
  名称：

  Optically Pure α-(Trimethylsilyl)benzyl Alcohol:  A Practical Chiral Auxiliary for Oxocarbenium Ion Reactions

  摘要：

  GRAPHICSEnantiopure (S)-alpha-(trimethylsilyl)benzyl alcohol (98% ee) was prepared by Noyori's transfer hydrogenation of benzoyltrimethylsilane. The corresponding trimethylsilyl ether was subjected to Marko's silyl modified Sakurai conditions with a variety of aldehydes to afford homoallylic ethers in high diastereoselectivity. The practicality of the alpha-trimethylsilyl benzyl group as an oxocarbenium ion auxiliary was further demonstrated by its efficient deprotection or conversion to a benzyl protecting group.

  DOI：

  10.1021/ol017063m

文献信息

• Optically Pure α-(Trimethylsilyl)benzyl Alcohol:  A Practical Chiral Auxiliary for Oxocarbenium Ion Reactions
  作者：Jennifer Cossrow、Scott D. Rychnovsky

  DOI：10.1021/ol017063m

  日期：2002.1.1

  GRAPHICSEnantiopure (S)-alpha-(trimethylsilyl)benzyl alcohol (98% ee) was prepared by Noyori's transfer hydrogenation of benzoyltrimethylsilane. The corresponding trimethylsilyl ether was subjected to Marko's silyl modified Sakurai conditions with a variety of aldehydes to afford homoallylic ethers in high diastereoselectivity. The practicality of the alpha-trimethylsilyl benzyl group as an oxocarbenium ion auxiliary was further demonstrated by its efficient deprotection or conversion to a benzyl protecting group.