2-Methylhex-5-yn-3-yloxy-bis(prop-2-enyl)silane | 372078-55-2

• 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: 2-Methylhex-5-yn-3-yloxy-bis(prop-2-enyl)silane
• 英文别名: 2-methylhex-5-yn-3-yloxy-bis(prop-2-enyl)silane
• CAS: 372078-55-2
• 化学式: C₁₃H₂₂OSi
• 分子量: 222.403
• InChiKey: JWZPFPCTESCCNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  15
• 可旋转键数：
  8
• 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：

  2-Methylhex-5-yn-3-yloxy-bis(prop-2-enyl)silane 在 acetylacetonatodicarbonylrhodium(l) 吡啶 作用下， 以 苯 为溶剂， 60.0 ℃ 、6.89 MPa 条件下， 反应 2.0h， 生成
  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
• 作为产物：
  描述：

  2-methyl-5-hexyn-3-ol 在 三氯硅烷 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 2-Methylhex-5-yn-3-yloxy-bis(prop-2-enyl)silane
  参考文献：
  名称：

  串联分子内炔基甲硅烷基化-烯丙基甲硅烷基化：远程1，5-不对称诱导的情况。

  摘要：

  标题反应中形成了两个新的CC键以及一个远程立体中心。通过远程1,5-不对称诱导，这种新反应以非凡的效率提供了反1,5-二醇，这些化合物可用于多元醇合成的合成子（参见方案； Hacac =乙酰丙酮）。

  DOI：

  10.1002/1521-3773(20010803)40:15<2915::aid-anie2915>3.0.co;2-9

文献信息

• 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.
• Tandem Intramolecular Alkyne Silylformylation-Allylsilylation: A Case of Remote 1,5-Asymmetric Induction
  作者：Steven J. O'Malley、James L. Leighton

  DOI：10.1002/1521-3773(20010803)40:15<2915::aid-anie2915>3.0.co;2-9

  日期：2001.8.3

  Two new C-C bonds as well as a remote stereocenter are formed in the title reaction. With remarkable efficiency, this new reaction provides, through remote 1,5-asymmetric induction, anti-1,5 diols that are useful synthons for polyol synthesis (see scheme; Hacac=acetylacetone).

  标题反应中形成了两个新的CC键以及一个远程立体中心。通过远程1,5-不对称诱导，这种新反应以非凡的效率提供了反1,5-二醇，这些化合物可用于多元醇合成的合成子（参见方案； Hacac =乙酰丙酮）。