2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-,ethyl ester, (2E,5S)- | 501373-16-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-,ethyl ester, (2E,5S)-
• 英文别名: (E)-ethyl 6-hydroxy-5-(S)-{[(1,1-dimethyl)ethyl dimethylsilyl]oxy}-2-hexenoate
• CAS: 501373-16-6
• 化学式: C₁₄H₂₈O₄Si
• 分子量: 288.459
• InChiKey: AKXGOCGFSYNROY-OANVXVOSSA-N

物化性质

• 沸点：
  344.0±42.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-,ethyl ester, (2E,5S)- 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 (E)-ethyl 6-{[(1,1-dimethyl)ethyl dimethylsilyl]oxy}-5-(S)-[(N-imidazole-thiocarbonyl)oxy]-2-hexenoate
  参考文献：
  名称：

  A New Reaction Manifold for the Barton Radical Intermediates:  Synthesis of N-Heterocyclic Furanosides and Pyranosides via the Formation of the C₁−C₂ Bond

  摘要：

  The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.

  DOI：

  10.1021/ja028617z
• 作为产物：
  描述：

  2-Furanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]tetrahydro-, (2S,4S)- 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 生成 2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-,ethyl ester, (2E,5S)- 、 (Z)-ethyl 6-hydroxy-5-(S)-{[(1,1-dimethyl)ethyl dimethylsilyl]oxy}-2-hexenoate
  参考文献：
  名称：

  A New Reaction Manifold for the Barton Radical Intermediates:  Synthesis of N-Heterocyclic Furanosides and Pyranosides via the Formation of the C₁−C₂ Bond

  摘要：

  The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.

  DOI：

  10.1021/ja028617z