(2S,3E)-7-(tert-butyldimethylsilyloxy)-2-hydroxyhept-3-enyl benzoate | 1226855-22-6

• 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,3E)-7-(tert-butyldimethylsilyloxy)-2-hydroxyhept-3-enyl benzoate
• 英文别名: [(E,2S)-7-[tert-butyl(dimethyl)silyl]oxy-2-hydroxyhept-3-enyl] benzoate
• CAS: 1226855-22-6
• 化学式: C₂₀H₃₂O₄Si
• 分子量: 364.557
• InChiKey: IAUPHZLLTDANSM-MDNBWPLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3E)-7-(tert-butyldimethylsilyloxy)-2-hydroxyhept-3-enyl benzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(2S,3E)-2,7-dihydroxyhept-3-enyl benzoate
  参考文献：
  名称：

  A Short Access to Chiral Non-Racemic Oxa- and Azaheterocycles by Cross-Metathesis and Pd-Catalyzed Cyclization Sequence

  摘要：

  A concise synthesis of chiral non-racemic 2-(3-benzoyloxyprop-1-enyl)tetrahydrofuran (5a), tetrahydropyran (5b), and piperidine (8) is described. Cross-metathesis of optically pure (S)-1-O-benzoyl-3-butene-1,2-diol (2) with protected 4-pentenol, 5-hexenol, and 5-hexenylamine gave the corresponding ally! alcohols (3a), (3b), and (7) in one step, respectively. PdCl(2)(MeCN)(2) catalyzed cyclization of 4a, 4b, and 7 afforded 5a, 5b, and 8 in excellent yields with high enantiomeric purity.

  DOI：

  10.3987/com-09-s(s)95
• 作为产物：
  描述：

  tert-butylpent-4-enyloxydimethylsilane 、 2-hydroxybut-3-en-1-yl benzoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(2S,3E)-7-(tert-butyldimethylsilyloxy)-2-hydroxyhept-3-enyl benzoate
  参考文献：
  名称：

  A Short Access to Chiral Non-Racemic Oxa- and Azaheterocycles by Cross-Metathesis and Pd-Catalyzed Cyclization Sequence

  摘要：

  A concise synthesis of chiral non-racemic 2-(3-benzoyloxyprop-1-enyl)tetrahydrofuran (5a), tetrahydropyran (5b), and piperidine (8) is described. Cross-metathesis of optically pure (S)-1-O-benzoyl-3-butene-1,2-diol (2) with protected 4-pentenol, 5-hexenol, and 5-hexenylamine gave the corresponding ally! alcohols (3a), (3b), and (7) in one step, respectively. PdCl(2)(MeCN)(2) catalyzed cyclization of 4a, 4b, and 7 afforded 5a, 5b, and 8 in excellent yields with high enantiomeric purity.

  DOI：

  10.3987/com-09-s(s)95

文献信息

• A Short Access to Chiral Non-Racemic Oxa- and Azaheterocycles by Cross-Metathesis and Pd-Catalyzed Cyclization Sequence
  作者：Jun'ichi Uenishi、Yogesh S. Vikhe

  DOI：10.3987/com-09-s(s)95

  日期：——

  A concise synthesis of chiral non-racemic 2-(3-benzoyloxyprop-1-enyl)tetrahydrofuran (5a), tetrahydropyran (5b), and piperidine (8) is described. Cross-metathesis of optically pure (S)-1-O-benzoyl-3-butene-1,2-diol (2) with protected 4-pentenol, 5-hexenol, and 5-hexenylamine gave the corresponding ally! alcohols (3a), (3b), and (7) in one step, respectively. PdCl(2)(MeCN)(2) catalyzed cyclization of 4a, 4b, and 7 afforded 5a, 5b, and 8 in excellent yields with high enantiomeric purity.