tributyl(4-ethoxy-4-oxobut-2-en-1-yl)antimony(V) tetraphenylborate | 132017-27-7

• 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: tributyl(4-ethoxy-4-oxobut-2-en-1-yl)antimony(V) tetraphenylborate
• CAS: 132017-27-7
• 化学式: C₁₈H₃₆O₂Sb*C₂₄H₂₀B
• 分子量: 725.466
• InChiKey: RDMQSZGFVIXHPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.02
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tributyl(4-ethoxy-4-oxobut-2-en-1-yl)antimony(V) tetraphenylborate 、 苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以81%的产率得到2E-5-hydroxy-5-phenyl-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Synthetic applications of elementoorganic compounds of group 15 and 16. 85. Pentaalkyl stiboranes. 1. Synthesis of homobenzylic alcohols, homoallylic alcohols, homoallylic alcohols, ethyl 5-aryl-5-hydroxy-2-pentenoates, and .beta.-hydroxypropionic acid derivatives via pentaalkylstiboranes

  摘要：

  Although pentaalkylstiboranes have long been known, their applications in organic synthesis have not been exploited. It has been found that quaternary stibonium salts (n-Bu3SbCH2E]+X- (E = Ph, CH = CH2, CH = CHCO2Et, CO2Et, CN; X = Br, I, BPh4) on treatment with RLi (R = n-Bu, t-Bu, Ph) afford pentaalkylstiboranes, n-Bu3Sb(R)CH2E, which react with aromatic aldehydes to give, after subsequent hydrolysis, homobenzylic alcohols, homoallylic alcohols, ethyl 5-aryl-5-hydroxypent-2-enoates, ethyl beta-aryl-beta-hydroxypropionates, and beta-aryl-beta-hydroxypropionitriles, respectively, in good to excellent yields. The reaction is chemoselective for aldehydes.

  DOI：

  10.1021/jo00004a010