Ethyl 5-hydroxy-5-(4-chlorophenyl)pent-2-enoate | 131973-47-2

• 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: Ethyl 5-hydroxy-5-(4-chlorophenyl)pent-2-enoate
• 英文别名: (+/-)-1-hydroxy-1-(4-chloro-phenyl)-penten-(3t)-oic acid-(5)-ethyl ester；(+/-)-1-Hydroxy-1-(4-chlor-phenyl)-penten-(3t)-saeure-(5)-aethylester；ethyl (E)-5-(4-chlorophenyl)-5-hydroxypent-2-enoate
• CAS: 131973-47-2
• 化学式: C₁₃H₁₅ClO₃
• 分子量: 254.713
• InChiKey: NENLTNQFJFLZOU-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 5-hydroxy-5-(4-chlorophenyl)pent-2-enoate 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5-(4-chlorophenyl)penta-(2E,4E)-dienoic acid
  参考文献：
  名称：

  Reformatsky Condensations Involving Vinylogs of Haloacetic Esters

  摘要：

  DOI：

  10.1021/ja01276a068
• 作为产物：
  描述：

  4-氯苯甲醛 、 tributyl(4-ethoxy-4-oxobut-2-en-1-yl)antimony(V) tetraphenylborate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到Ethyl 5-hydroxy-5-(4-chlorophenyl)pent-2-enoate
  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

文献信息

• 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
  作者：Yaozeng Huang、Yi Liao

  DOI：10.1021/jo00004a010

  日期：1991.2

  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.
• Reformatsky Condensations Involving Vinylogs of Haloacetic Esters
  作者：Reynold C. Fuson、R. T. Arnold、H. G. Cooke

  DOI：10.1021/ja01276a068

  日期：1938.9