4-(diallylsilyloxy)-5-methyl-hex-1-ene | 302322-80-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(diallylsilyloxy)-5-methyl-hex-1-ene
• 英文别名: 2-Methylhex-5-en-3-yloxy-bis(prop-2-enyl)silane；2-methylhex-5-en-3-yloxy-bis(prop-2-enyl)silane
• CAS: 302322-80-1
• 化学式: C₁₃H₂₄OSi
• 分子量: 224.418
• InChiKey: WHHGYKYGFXLECV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  一氧化碳 、 4-(diallylsilyloxy)-5-methyl-hex-1-ene 在 acetylacetonatodicarbonylrhodium(l) 、 双氧水 、 碳酸氢钠 作用下， 以 苯 、 四氢呋喃 、 甲醇 为溶剂， 60.0 ℃ 、6.89 MPa 条件下， 以59%的产率得到4,6-syn-6,8-syn-9-methyl-dec-1-ene-4,6,8-triol
  参考文献：
  名称：

  串联分子内甲硅烷基化-烯丙基甲硅烷基化

  摘要：

  DOI：

  10.1021/ja002425r
• 作为产物：
  描述：

  2-甲基-5-己烯-3-醇 、 烯丙基溴化镁 在 三氯硅烷 作用下， 以 乙醚 为溶剂， 生成 4-(diallylsilyloxy)-5-methyl-hex-1-ene
  参考文献：
  名称：

  Tandem silylformylation–allyl(crotyl)silylation: a new approach to polyketide synthesis

  摘要：

  Tandem intramolecular silylformylation-allyl(crotyl)silylation reactions have been developed that allow the highly efficient synthesis of polyketide fragments. The substrates are subjected to Rh(I)-catalyzed silylformylation to afford beta-(diallyl)silyl aldehydes which undergo spontaneous uncatalyzed allylsilylation. This unusual spontaneous allylsilylation reaction is driven by strain release Lewis acidity, which arises from the similar to95degrees O-Si-C bond angle in the oxasilacyclopentane product of the silylformylation reaction. The methodology has been developed both for alkene and alkyne substrates, may be used to establish as many as three stereocenters, and has been shown to be amenable to use in an iterative fashion. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.04.004

文献信息

• Tandem Intramolecular Silylformylation−Allylsilylation
  作者：Michael J. Zacuto、James L. Leighton

  DOI：10.1021/ja002425r

  日期：2000.9.1
• Tandem silylformylation–allyl(crotyl)silylation: a new approach to polyketide synthesis
  作者：Michael J. Zacuto、Steven J. O'Malley、James L. Leighton

  DOI：10.1016/j.tet.2003.04.004

  日期：2003.11

  Tandem intramolecular silylformylation-allyl(crotyl)silylation reactions have been developed that allow the highly efficient synthesis of polyketide fragments. The substrates are subjected to Rh(I)-catalyzed silylformylation to afford beta-(diallyl)silyl aldehydes which undergo spontaneous uncatalyzed allylsilylation. This unusual spontaneous allylsilylation reaction is driven by strain release Lewis acidity, which arises from the similar to95degrees O-Si-C bond angle in the oxasilacyclopentane product of the silylformylation reaction. The methodology has been developed both for alkene and alkyne substrates, may be used to establish as many as three stereocenters, and has been shown to be amenable to use in an iterative fashion. (C) 2003 Elsevier Ltd. All rights reserved.