5-(ethynyl)-5-(trimethylsilyloxy)non-1-en-8-yne | 141738-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(ethynyl)-5-(trimethylsilyloxy)non-1-en-8-yne
• 英文别名: 5-Ethynylnon-1-en-8-yn-5-yloxy(trimethyl)silane
• CAS: 141738-81-0
• 化学式: C₁₄H₂₂OSi
• 分子量: 234.414
• InChiKey: FMKKHGXTGDMURW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  5-(ethynyl)-5-(trimethylsilyloxy)non-1-en-8-yne 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基吲哚酮 作用下， 生成 all-cis-7-(trimethylsilyloxy)tetracyclo<5.5.1.0^4,13.0^10,13>tridec-3-ene-2,12-dione
  参考文献：
  名称：

  Fenestranes in Recent Synthetic Developments

  摘要：

  本文概述并特别讨论了四坐标碳平面化畸变的系统描述，其中C(C)4部分构成了fenestranes的中心部分。本文还描述了立体异构体[4.5.5.5]fenestranes和[5.5.5.5]fenestranes的合成制备的最新进展。文中还介绍了旨在增加平面化畸变的转化。Fe2(CO)9与fenestradiene的相互作用产生了三种结构明确的Fe-羰基配合物。

  DOI：

  10.1055/s-1997-755
• 作为产物：
  描述：

  non-1-en-8-yn-5-one 在 乙基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.17h， 生成 5-(ethynyl)-5-(trimethylsilyloxy)non-1-en-8-yne
  参考文献：
  名称：

  The TandemPauson-Khand Reaction

  摘要：

  AbstractThe conditions for the novel tandem Pauson‐Khand reaction have been explored. The highly functionalized tetracyclic compounds 11c, 11d, and 16 were prepared from the ene‐diynes 4c, 4d, and 10 by treatment with 2 equiv. of [Co2(CO)8] and 4‐methylmorpholine N‐oxide (NMO) or Me3NO in yields of 24, 22, and 53%, respectively (Table). In the presence of 1–3 equiv. of H2O added to the NMO used for induction of the Pauson‐Khand reaction of 6d, a mixture of cyclopentanones 17/18 and cyclopentenones 12/13 was obtained (Scheme 5). The first example of a [Co2(CO)6]‐induced highly stereoselective ene reaction is described. To account for these results, the formation of intermediates are proposed (Schemes 6 and 7) which hitherto have not been considered in the mechanistic description of the Pauson‐Khand reaction.

  DOI：

  10.1002/hlca.19960790214

文献信息

• The TandemPauson-Khand Reaction
  作者：Marc Thommen、Andrei L. Veretenov、R�gine Guidetti-Grept、Reinhart Keese

  DOI：10.1002/hlca.19960790214

  日期：1996.3.20

  AbstractThe conditions for the novel tandem Pauson‐Khand reaction have been explored. The highly functionalized tetracyclic compounds 11c, 11d, and 16 were prepared from the ene‐diynes 4c, 4d, and 10 by treatment with 2 equiv. of [Co2(CO)8] and 4‐methylmorpholine N‐oxide (NMO) or Me3NO in yields of 24, 22, and 53%, respectively (Table). In the presence of 1–3 equiv. of H2O added to the NMO used for induction of the Pauson‐Khand reaction of 6d, a mixture of cyclopentanones 17/18 and cyclopentenones 12/13 was obtained (Scheme 5). The first example of a [Co2(CO)6]‐induced highly stereoselective ene reaction is described. To account for these results, the formation of intermediates are proposed (Schemes 6 and 7) which hitherto have not been considered in the mechanistic description of the Pauson‐Khand reaction.
• Fenestranes in Recent Synthetic Developments
  作者：M. Thommen、Reinhart Keese

  DOI：10.1055/s-1997-755

  日期：1997.3

  The systematic description of planarizing distortions of tetracoordinate carbon is outlined and specifically discussed for C(C)4 moieties which form the central part of fenestranes. Recent synthetic developments of the preparation of stereoisomeric [4.5.5.5]fenestranes and [5.5.5.5]fenestranes are described. Transformations with the aim of increased planarizing distortions are presented. The interaction of Fe2(CO)9 with a fenestradiene led to three structurally well defined Fe-carbonyl complexes.

  本文概述并特别讨论了四坐标碳平面化畸变的系统描述，其中C(C)4部分构成了fenestranes的中心部分。本文还描述了立体异构体[4.5.5.5]fenestranes和[5.5.5.5]fenestranes的合成制备的最新进展。文中还介绍了旨在增加平面化畸变的转化。Fe2(CO)9与fenestradiene的相互作用产生了三种结构明确的Fe-羰基配合物。