5-(ethyl)-5-<(methyl)diphenylsilyloxy>nona-1,8-diene | 177196-51-9

• 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: 5-(ethyl)-5-<(methyl)diphenylsilyloxy>nona-1,8-diene
• 英文别名: 5-ethynylnona-1,8-dien-5-yloxy-methyl-diphenylsilane
• CAS: 177196-51-9
• 化学式: C₂₄H₂₈OSi
• 分子量: 360.571
• InChiKey: VQRZXLDSBSWHBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(ethyl)-5-<(methyl)diphenylsilyloxy>nona-1,8-diene 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基吗啉氧化物 作用下， 生成 (4S,6aS)-4-But-3-enyl-4-(methyl-diphenyl-silanyloxy)-4,5,6,6a-tetrahydro-1H-pentalen-2-one 、 (4S,6aR)-4-But-3-enyl-4-(methyl-diphenyl-silanyloxy)-4,5,6,6a-tetrahydro-1H-pentalen-2-one
  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
• 作为产物：
  描述：

  4-戊烯酰氯 在 咪唑 、 乙二胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 5-(ethyl)-5-<(methyl)diphenylsilyloxy>nona-1,8-diene
  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.