carbethoxymethyltri-n-butylstibonium tetraphenylborate | 123843-32-3

• 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: carbethoxymethyltri-n-butylstibonium tetraphenylborate
• 英文别名: tetraphenylboranuide;tributyl-(2-ethoxy-2-oxoethyl)stibanium
• CAS: 123843-32-3
• 化学式: C₁₆H₃₄O₂Sb*C₂₄H₂₀B
• 分子量: 699.429
• InChiKey: RMJZHBCXENFFOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.46
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  carbethoxymethyltri-n-butylstibonium tetraphenylborate 、 4-甲氧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以93%的产率得到(+/-)-ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate
  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
• 作为产物：
  描述：

  ethyl 2-[bromo(tributyl)-λ5-stibanyl]acetate 、 四苯硼钠 以47%的产率得到
  参考文献：
  名称：

  HUANG, YAO-ZENG;CHEN, CHEN;SHEN, YANCHANG, J. ORGANOMET. CHEM., 366,(1989) N-2, C. 87-93

  摘要：

  DOI：

文献信息

• Studies of the use of elemento-organic compounds of the fifteenth and sixteenth groups in organic synthesis LXXI. Reaction of α-halogeno carboxylic derivatives with carbonyl compounds promoted by tributylstibine
  作者：Yao-Zeng Huang、Chen Chen、Yanchang Shen

  DOI：10.1016/0022-328x(89)87318-8

  日期：1989.4

  α,β-Unsaturated esters and amides were conveniently obtained from the trialkylstibine-promoted reaction of α-halogenocarboxylic derivatives with carbonyl compounds. In this reaction, a quaternary stibonium salt is an active intermediate that can be trapped and can undergo further reaction with the substrate.

  从α-卤代羧酸衍生物与羰基化合物的三烷基苯乙烯促进的反应中方便地获得α，β-不饱和酯和酰胺。在该反应中，季sti盐是一种活性中间体，可以被捕获并与底物进行进一步反应。