7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol | 119554-49-3

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol
• 英文别名: 7-hydroxy-1-trimethylsilyl-2-heptene；7-(Trimethylsilyl)hept-5-en-1-ol；7-trimethylsilylhept-5-en-1-ol
• CAS: 119554-49-3
• 化学式: C₁₀H₂₂OSi
• 分子量: 186.37
• InChiKey: XROJZDXHOJRWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol 在 重铬酸吡啶 作用下， 生成 7-trimethylsilyl-5-hepten-1-al
  参考文献：
  名称：

  有机硅化学中的新反应：烯丙基硅烷与硝酸铈铵的氧化闭环

  摘要：

  当用（NH 4）2 Ce（NO 3）6处理时，含有杂原子亲核试剂的烯丙基硅烷会产生环状产物。例如，含羟基和含酰胺基的烯丙基硅烷可产生相应的四氢呋喃，四氢吡喃和哌啶类似物。将讨论这些反应及其在天然产物合成中的应用。

  DOI：

  10.1016/s0040-4020(01)86650-3
• 作为产物：
  描述：

  tetrahydro-2H-2-pyranol 、 (2-trimethylsilylethylidene)triphenylphosphorane 以 四氢呋喃 为溶剂， 以80%的产率得到7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol
  参考文献：
  名称：

  有机合成中的烯丙基硅烷环化；通过环氧烯丙基硅烷环化形成环戊烷

  摘要：

  环氧烯丙基硅烷（1）通过两种途径制备，并进行立体选择性环化，得到TiCl 4处理的顺环戊烷（9）; 对应于（9）的醛的平衡得到高产率的反式异构体。

  DOI：

  10.1039/c39840000585

文献信息

• Allylsilane cyclisations in organic synthesis; formation of a cyclopentane via cyclisation of an epoxy-allylsilane
  作者：Thuan Siah Tan、Andrew N. Mather、Garry Procter、Alan H. Davidson

  DOI：10.1039/c39840000585

  日期：——

  The epoxy-allylsilane (1) was prepared by two routes and cyclised stereoselectively to give the cis-cyclopentane (9) on treatment with TiCl4; equilibration of the aldehyde corresponding to (9) gave the trans-isomer in high yield.

  环氧烯丙基硅烷（1）通过两种途径制备，并进行立体选择性环化，得到TiCl 4处理的顺环戊烷（9）; 对应于（9）的醛的平衡得到高产率的反式异构体。
• A new reaction in organosilicon chemistry: the oxidative ring closure of allylsilanes with ceric ammonium nitrate
  作者：Stephen R. Wilson、Corinne E. Augelli-Szafran

  DOI：10.1016/s0040-4020(01)86650-3

  日期：1988.1

  Allylsilanes containing heteroatom nucleophiles yield cyclic products when treated with (NH4)2Ce(NO3)6. For example, hydroxy and amido-containing allylsilanes yield the corresponding tetrahydrofuran, tetrahydropyran, and piperidine analogs. These reactions and their application to natural product synthesis will be discussed.

  当用（NH 4）2 Ce（NO 3）6处理时，含有杂原子亲核试剂的烯丙基硅烷会产生环状产物。例如，含羟基和含酰胺基的烯丙基硅烷可产生相应的四氢呋喃，四氢吡喃和哌啶类似物。将讨论这些反应及其在天然产物合成中的应用。
• Epoxy-silanes in organic synthesis
  作者：Garry Procter、Andrew T. Russell、Patrick J. Murphy、T.S. Tan、Andrew N. Mather

  DOI：10.1016/s0040-4020(01)86648-5

  日期：1988.1
• Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation
  作者：Christine M. Hudson、Mohammad R. Marzabadi、Kevin D. Moeller、Dallas G. New

  DOI：10.1021/ja00019a038

  日期：1991.9

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.
• Total synthesis of (+)-brefeldin C via Lewis acid mediated cyclization of an epoxy-allylsilane
  作者：Susumi Hatakeyama、Ken Osanai、Hirotoshi Numata、Seiichi Takano

  DOI：10.1016/s0040-4039(01)80524-4

  日期：——

  An enantioselective synthesis of (+)-brefeldin C has been achieved using Lewis acid mediated cyclization of a chiral epoxy-allylsilane as a key step.

  使用路易斯酸介导的手性环氧烯丙基硅烷的环化作为关键步骤，已经实现了对（+）-布雷菲德菌素C的对映选择性合成。