(S)-1-(trimethylsilyl)tridec-1-yn-3-ol | 946514-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-(trimethylsilyl)tridec-1-yn-3-ol
• 英文别名: (3S)-1-trimethylsilyltridec-1-yn-3-ol
• CAS: 946514-58-5
• 化学式: C₁₆H₃₂OSi
• 分子量: 268.515
• InChiKey: VGUKZSDTAJMIIQ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (S)-1-(trimethylsilyl)tridec-1-yn-3-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 氘代甲醇-d 、 2-硝基苯磺酰肼 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 氘代甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Development, Mechanism, and Scope of the Palladium-Catalyzed Enantioselective Allene Diboration

  摘要：

  In the presence of a chiral phosphoramidite ligand, the palladium-catalyzed diboration of allenes can be executed with high enantioselectivity. This reaction provides high levels of selectivity with a range of aromatic and aliphatic allene substrates. Isotopic-labeling experiments, stereodifferentiating reactions, kinetic analysis, and computational experiments suggest that the catalytic cycle proceeds by a mechanism involving rate-determining oxidative addition of the diboron to Pd followed by transfer of both boron groups to the unsaturated substrate. This transfer reaction most likely occurs by coordination and insertion of the more accessible terminal alkene of the allene substrate, by a mechanism that directly provides the eta(3) pi-allyl complex in a stereospecific, concerted fashion.

  DOI：

  10.1021/ja070572k
• 作为产物：
  描述：

  十一醛 在 Ru[(1S,2S)-p-TsNCH(C6H5)CH(C6H5)NH](η⁶-p-cymene) 重铬酸吡啶 、 正丁基锂 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 34.0h， 生成 (S)-1-(trimethylsilyl)tridec-1-yn-3-ol
  参考文献：
  名称：

  Development, Mechanism, and Scope of the Palladium-Catalyzed Enantioselective Allene Diboration

  摘要：

  In the presence of a chiral phosphoramidite ligand, the palladium-catalyzed diboration of allenes can be executed with high enantioselectivity. This reaction provides high levels of selectivity with a range of aromatic and aliphatic allene substrates. Isotopic-labeling experiments, stereodifferentiating reactions, kinetic analysis, and computational experiments suggest that the catalytic cycle proceeds by a mechanism involving rate-determining oxidative addition of the diboron to Pd followed by transfer of both boron groups to the unsaturated substrate. This transfer reaction most likely occurs by coordination and insertion of the more accessible terminal alkene of the allene substrate, by a mechanism that directly provides the eta(3) pi-allyl complex in a stereospecific, concerted fashion.

  DOI：

  10.1021/ja070572k

文献信息

• Development, Mechanism, and Scope of the Palladium-Catalyzed Enantioselective Allene Diboration
  作者：Heather E. Burks、Shubin Liu、James P. Morken

  DOI：10.1021/ja070572k

  日期：2007.7.1

  In the presence of a chiral phosphoramidite ligand, the palladium-catalyzed diboration of allenes can be executed with high enantioselectivity. This reaction provides high levels of selectivity with a range of aromatic and aliphatic allene substrates. Isotopic-labeling experiments, stereodifferentiating reactions, kinetic analysis, and computational experiments suggest that the catalytic cycle proceeds by a mechanism involving rate-determining oxidative addition of the diboron to Pd followed by transfer of both boron groups to the unsaturated substrate. This transfer reaction most likely occurs by coordination and insertion of the more accessible terminal alkene of the allene substrate, by a mechanism that directly provides the eta(3) pi-allyl complex in a stereospecific, concerted fashion.