(R)-4-Chloro-3-trimethylsilanyloxy-butyric acid ethyl ester | 139071-36-6

• 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: (R)-4-Chloro-3-trimethylsilanyloxy-butyric acid ethyl ester
• 英文别名: ethyl (3R)-4-chloro-3-trimethylsilyloxybutanoate
• CAS: 139071-36-6
• 化学式: C₉H₁₉ClO₃Si
• 分子量: 238.787
• InChiKey: QHJVUPNWWYOJIL-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-Chloro-3-trimethylsilanyloxy-butyric acid ethyl ester 在 二异丁基氢化铝 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 1.5h， 以3.25 g的产率得到丁醛,4-氯-3-[(三甲基甲硅烷基)氧代]-,(R)-
  参考文献：
  名称：

  An iterative and convergent synthesis of syn polyols

  摘要：

  We have developed a new iterative and convergent synthesis of alternating (1,3,5...) polyol chains based on enantiomerically enriched (94% ee) chloro nitrile 1. Chloro nitrile 1 is both a potential nucleophile and a potential electrophile; orthogonal nucleophilic or electrophilic activation leads to a highly efficient synthetic strategy for alternating polyol chains. As an illustration permethylated polyol 2 (n = 10), a natural product with 10 stereogenic centers isolated from the blue green alga Tolypothrix conglutinata var. chlorata, was prepared in 10 steps from 1.

  DOI：

  10.1021/jo00031a041
• 作为产物：
  描述：

  N,N-二甲基三甲基硅胺 、 (R)-(+)-4-氯-3-羟基丁酸乙酯 反应 16.0h， 以4.31 g的产率得到(R)-4-Chloro-3-trimethylsilanyloxy-butyric acid ethyl ester
  参考文献：
  名称：

  An iterative and convergent synthesis of syn polyols

  摘要：

  We have developed a new iterative and convergent synthesis of alternating (1,3,5...) polyol chains based on enantiomerically enriched (94% ee) chloro nitrile 1. Chloro nitrile 1 is both a potential nucleophile and a potential electrophile; orthogonal nucleophilic or electrophilic activation leads to a highly efficient synthetic strategy for alternating polyol chains. As an illustration permethylated polyol 2 (n = 10), a natural product with 10 stereogenic centers isolated from the blue green alga Tolypothrix conglutinata var. chlorata, was prepared in 10 steps from 1.

  DOI：

  10.1021/jo00031a041