benzyl 2-(allyldimethylsilyloxy)-4-penten-1-yl ether | 193557-34-5

• 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: benzyl 2-(allyldimethylsilyloxy)-4-penten-1-yl ether
• 英文别名: Dimethyl-(1-phenylmethoxypent-4-en-2-yloxy)-prop-2-enylsilane
• CAS: 193557-34-5
• 化学式: C₁₇H₂₆O₂Si
• 分子量: 290.478
• InChiKey: SOUOONSOLLPSKV-UHFFFAOYSA-N

物化性质

• 沸点：
  329.2±42.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 2-(allyldimethylsilyloxy)-4-penten-1-yl ether 在 [bis(tricyclohexylphosphine)](benzylidene) Ru(IV) dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (Z)-1-phenylmethoxy-6-trimethylsilylhex-4-en-2-ol
  参考文献：
  名称：

  Oligocyclopropane Structural Units from Cationic Intermediates

  摘要：

  [GRAPHICS]syn- and anti-bis-cyclopropanes have been efficiently prepared through two distinct routes via the trapping of cyclopropylcarbinyl cationic intermediates. A ring-closing olefin metathesis for the formation of the necessary allylsilane precursors highlights the initial route. The cyclopropanation step proceeds in good yield to provide exclusively trans-vinylcyclopropanes. Iteration of the sequence has provided an efficient route to bis-cyclopropanes. The stereospecificity of the second cyclization was shown to be dependent on distal functionality. An alternative approach produces these interesting structural units from skipped dienes in a single step.

  DOI：

  10.1021/ol990221d
• 作为产物：
  描述：

  苄基缩水甘油醚 在 咪唑 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 benzyl 2-(allyldimethylsilyloxy)-4-penten-1-yl ether
  参考文献：
  名称：

  Oligocyclopropane Structural Units from Cationic Intermediates

  摘要：

  [GRAPHICS]syn- and anti-bis-cyclopropanes have been efficiently prepared through two distinct routes via the trapping of cyclopropylcarbinyl cationic intermediates. A ring-closing olefin metathesis for the formation of the necessary allylsilane precursors highlights the initial route. The cyclopropanation step proceeds in good yield to provide exclusively trans-vinylcyclopropanes. Iteration of the sequence has provided an efficient route to bis-cyclopropanes. The stereospecificity of the second cyclization was shown to be dependent on distal functionality. An alternative approach produces these interesting structural units from skipped dienes in a single step.

  DOI：

  10.1021/ol990221d

文献信息

• A simple method to polyhydroxylated olefinic molecules using ring-closing olefin metathesis
  作者：Sukbok Chang、Robert H. Grubbs

  DOI：10.1016/s0040-4039(97)01031-9

  日期：1997.7

  This paper describes the ring-closing metathesis of silyl ether connected dienes using molybdenum and ruthenium alkylidene catalysts. The cyclizations proceed to afford the corresponding cyclic silyloxy olefins in good to excellent yields. Subsequent oxidative ring cleavage yields highly functionalized olefins.

  本文介绍了使用钼和钌亚烷基催化剂在甲硅烷基醚连接的二烯上进行的闭环复分解反应。进行环化反应以良好或优异的产率得到相应的环状甲硅烷基氧基烯烃。随后的氧化环裂解产生高度官能化的烯烃。