[(E)-9-(3,3-Dimethyl-oxiranyl)-7-methyl-non-6-en-2-ynyl]-trimethyl-silane | 186249-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: [(E)-9-(3,3-Dimethyl-oxiranyl)-7-methyl-non-6-en-2-ynyl]-trimethyl-silane
• 英文别名: [(E)-9-(3,3-dimethyloxiran-2-yl)-7-methylnon-6-en-2-ynyl]-trimethylsilane
• CAS: 186249-84-3
• 化学式: C₁₇H₃₀OSi
• 分子量: 278.51
• InChiKey: JESOPANBDSUUSA-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(E)-9-(3,3-Dimethyl-oxiranyl)-7-methyl-non-6-en-2-ynyl]-trimethyl-silane 在 4 A molecular sieve 作用下， 以 氯仿 为溶剂， 反应 0.67h， 以100%的产率得到(3aS,5R,7aR)-4,4,7a-Trimethyl-1-vinylidene-octahydro-inden-5-ol
  参考文献：
  名称：

  Zeolite-Mediated Cyclization of an Epoxide-Containing Polyene

  摘要：

  The utility of zeolites as promoters for the cyclization of an epoxide-containing polyene has been investigated. Reaction of polyene 1 with oven-dried 4 Angstrom molecular sieves (type A zeolite) proceeds efficiently to generate bicyclic alcohol 2 in a 90% isolated yield. The reaction is sensitive to a variety of factors, including solvent type, water content, and zeolite acidity. Reactivity is apparently due to the zeolite lattice, since alumina and silica either are unreactive or generate a complex mixture of epoxide ring-opened products. Compared to the aluminum-based Lewis acid Me(2)AlCl, the zeolite-promoted cyclization of 1 was a more facile reaction, providing excellent product recovery after filtration. These results indicate that zeolites represent a new class of promoters in biomimetic polyene cyclizations.

  DOI：

  10.1021/jo960745g
• 作为产物：
  描述：

  diphenylisopropylsulfonium tetrafluoroborate 、 (E)-4-methyl-10-trimethylsilyldec-4-en-8-ynal 在 叔丁基锂 作用下， 生成 [(E)-9-(3,3-Dimethyl-oxiranyl)-7-methyl-non-6-en-2-ynyl]-trimethyl-silane
  参考文献：
  名称：

  Zeolite-Mediated Cyclization of an Epoxide-Containing Polyene

  摘要：

  The utility of zeolites as promoters for the cyclization of an epoxide-containing polyene has been investigated. Reaction of polyene 1 with oven-dried 4 Angstrom molecular sieves (type A zeolite) proceeds efficiently to generate bicyclic alcohol 2 in a 90% isolated yield. The reaction is sensitive to a variety of factors, including solvent type, water content, and zeolite acidity. Reactivity is apparently due to the zeolite lattice, since alumina and silica either are unreactive or generate a complex mixture of epoxide ring-opened products. Compared to the aluminum-based Lewis acid Me(2)AlCl, the zeolite-promoted cyclization of 1 was a more facile reaction, providing excellent product recovery after filtration. These results indicate that zeolites represent a new class of promoters in biomimetic polyene cyclizations.

  DOI：

  10.1021/jo960745g

文献信息

• Zeolite-Mediated Cyclization of an Epoxide-Containing Polyene
  作者：Stephanie E. Sen、Yan zhi Zhang、Steven L. Roach

  DOI：10.1021/jo960745g

  日期：1996.1.1

  The utility of zeolites as promoters for the cyclization of an epoxide-containing polyene has been investigated. Reaction of polyene 1 with oven-dried 4 Angstrom molecular sieves (type A zeolite) proceeds efficiently to generate bicyclic alcohol 2 in a 90% isolated yield. The reaction is sensitive to a variety of factors, including solvent type, water content, and zeolite acidity. Reactivity is apparently due to the zeolite lattice, since alumina and silica either are unreactive or generate a complex mixture of epoxide ring-opened products. Compared to the aluminum-based Lewis acid Me(2)AlCl, the zeolite-promoted cyclization of 1 was a more facile reaction, providing excellent product recovery after filtration. These results indicate that zeolites represent a new class of promoters in biomimetic polyene cyclizations.