(2S)-2-O-tert-butyldimethylsilyl-5-O-trimethylsilyl-7-phenyl-5-(phenyl)ethynyl-(3E)-hepten-6-yne-2,5-diol | 693782-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-O-tert-butyldimethylsilyl-5-O-trimethylsilyl-7-phenyl-5-(phenyl)ethynyl-(3E)-hepten-6-yne-2,5-diol
• 英文别名: tert-butyl-dimethyl-[(E,2S)-7-phenyl-5-(2-phenylethynyl)-5-trimethylsilyloxyhept-3-en-6-yn-2-yl]oxysilane
• CAS: 693782-88-6
• 化学式: C₃₀H₄₀O₂Si₂
• 分子量: 488.817
• InChiKey: UMSHLHMOFYTOOC-ZDXMMURSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  烯丙基三甲基硅烷 、 (2S)-2-O-tert-butyldimethylsilyl-5-O-trimethylsilyl-7-phenyl-5-(phenyl)ethynyl-(3E)-hepten-6-yne-2,5-diol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)]ethyl-8-phenyl-6-(phenylethynyl)-1,5-octadien-7-yne 、 (4S)-4-[(1S)-1-(tert-butyldimethylsiloxy)]ethyl-8-phenyl-6-(phenylethynyl)-1,5-octadien-7-yne
  参考文献：
  名称：

  Diastereoselective Allylations of Allyl−Propargyl Hybrid Cations:  Synthesis of Conjugated 1,5-Dien-7-yne Frameworks Bearing C(4)-Stereogenic Centers

  摘要：

  Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with (BF3OEt2)-O-. in CH2Cl2 at -50 degreesC in the presence of allyltrimethylsilane. The Cieplak conformation for (E)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

  DOI：

  10.1021/ol049847g
• 作为产物：
  描述：

  (S,E)-ethyl 4-((tert-butyldimethylsilyl)oxy)pent-2-enoate 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.58h， 生成 (2S)-2-O-tert-butyldimethylsilyl-5-O-trimethylsilyl-7-phenyl-5-(phenyl)ethynyl-(3E)-hepten-6-yne-2,5-diol
  参考文献：
  名称：

  Diastereoselective Allylations of Allyl−Propargyl Hybrid Cations:  Synthesis of Conjugated 1,5-Dien-7-yne Frameworks Bearing C(4)-Stereogenic Centers

  摘要：

  Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with (BF3OEt2)-O-. in CH2Cl2 at -50 degreesC in the presence of allyltrimethylsilane. The Cieplak conformation for (E)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

  DOI：

  10.1021/ol049847g