6-(1-propynyl)-6-<(triethylsilyl)oxy>-1,10-undecadiene | 160314-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(1-propynyl)-6-<(triethylsilyl)oxy>-1,10-undecadiene
• 英文别名: Triethyl(6-prop-1-ynylundeca-1,10-dien-6-yloxy)silane
• CAS: 160314-24-9
• 化学式: C₂₀H₃₆OSi
• 分子量: 320.591
• InChiKey: DGBIAJLLCSUGGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  6-(1-propynyl)-6-<(triethylsilyl)oxy>-1,10-undecadiene 在 ruthenium carbene complex 作用下， 以 苯 为溶剂， 反应 8.0h， 以88%的产率得到2-methyl-7-<(triethylsilyl)oxy>bicyclo<5.4.0>undeca-2,11-diene
  参考文献：
  名称：

  Catalytic Ring Closing Metathesis of Dienynes:  Construction of Fused Bicyclic [n.m.0] Rings

  摘要：

  Ruthenium carbene 1 (Cl-2(PCy(3))(2)Ru=CHCH=CPh(2)) mediates the efficient and selective conversion of acyclic dienynes to fused bicyclic [n.m.O] rings containing five-, six-, and seven-membered rings. Studies with various X-substituted acetylenes (X=H, alkyls, Ph, CO(2)Me, SnBu(3), TMS, Cl, Pr, I) suggest that the dienyne metathesis is sensitive not only to these substituents but also to the catalysts employed. Among the various metal alkylidenes examined, only the ruthenium catalyst 1 exhibited metathesis activity for a range of substrates. These observations further expand the scope of catalytic RCM for the construction of complex organic compounds.

  DOI：

  10.1021/jo951648a
• 作为产物：
  描述：

  5-溴-1-戊烯 在 magnesium 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 6-(1-propynyl)-6-<(triethylsilyl)oxy>-1,10-undecadiene
  参考文献：
  名称：

  Catalytic Ring Closing Metathesis of Dienynes:  Construction of Fused Bicyclic [n.m.0] Rings

  摘要：

  Ruthenium carbene 1 (Cl-2(PCy(3))(2)Ru=CHCH=CPh(2)) mediates the efficient and selective conversion of acyclic dienynes to fused bicyclic [n.m.O] rings containing five-, six-, and seven-membered rings. Studies with various X-substituted acetylenes (X=H, alkyls, Ph, CO(2)Me, SnBu(3), TMS, Cl, Pr, I) suggest that the dienyne metathesis is sensitive not only to these substituents but also to the catalysts employed. Among the various metal alkylidenes examined, only the ruthenium catalyst 1 exhibited metathesis activity for a range of substrates. These observations further expand the scope of catalytic RCM for the construction of complex organic compounds.

  DOI：

  10.1021/jo951648a

文献信息

• Catalytic Ring Closing Metathesis of Dienynes: Construction of Fused Bicyclic Rings
  作者：Soong-Hoon Kim、Ned Bowden、Robert H. Grubbs

  DOI：10.1021/ja00102a062

  日期：1994.11
• Kim Soong-Hoon, Bowden Ned, Crubbs Robert H., J. Amer. Chem. Soc, 116 (1994) N 23, S 10801-10802
  作者：Kim Soong-Hoon, Bowden Ned, Crubbs Robert H.

  DOI：——

  日期：——