Ethyl 5-oxo-9-phenyl-6-(β-styryl)-8-nonenoate | 140462-83-5

• 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-oxo-9-phenyl-6-(β-styryl)-8-nonenoate
• 英文别名: ethyl (E)-5-oxo-9-phenyl-6-[(E)-2-phenylethenyl]non-8-enoate
• CAS: 140462-83-5
• 化学式: C₂₅H₂₈O₃
• 分子量: 376.496
• InChiKey: AFCRKXRFDITRFG-CIGHJNMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  一氧化碳 、 (E)-苯甲酸肉桂酯 、 γ-(Iodzinkio)buttersaeureethylester 在 四(三苯基膦)钯 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以70%的产率得到Ethyl 5-oxo-8-phenyl-7-octenoate
  参考文献：
  名称：

  Tamaru, Yoshinao; Yasui, Kengo; Takanabe, Hidenobu, Angewandte Chemie, 1992, vol. 104, # 5, p. 662 - 664

  摘要：

  DOI：

文献信息

• Unsymmetrical Ketone Synthesis via a Three-Component Connection Reaction of Organozincs, Allylating Agents, and Carbon Monoxide
  作者：Kengo Yasui、Keigo Fugami、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00110a047

  日期：1995.3

  A wide variety of organozincs (diethylzinc, alkylzinc halides, and organozincs 2, 5, and 9a-e, functionalized with ester and nitrile groups) undergo a three-component connection reaction with carbon monoxide and allylic benzoates or phosphates 1a-h to furnish unsymmetrical ketones, e.g., 3, 6, and 10, in good yields under 1 atm of carbon monoxide at ambient temperature by the catalysis of tetrakis(triphenylphosphine)palladium in THF/HMPA. The regio- and stereoselectivities of the present carbonylation show marked contrast to those reported for the palladium-catalyzed carbonylation of unsymmetrical allylic substrates. For example, the reaction of crotyl benzoate with octylzinc iodide provides all the possible stereo- and regioisomers, i.e., cis- and trans-2-butenyl and 1-methyl-2-propenyl octyl ketones in comparable amounts. The carbonylative coupling of carvyl phosphates, trans- and cis-1h, and gamma-zincio ester 5 is stereospecific and proceeds with inversion of configuration at the allylic stereocenters to furnish cis- and trans-6h, respectively, as single diastereomers. In the absence of HMPA, the reaction feature changes dramatically and lactones 12 and 13 (composed of organozincs, carbon monoxide, and allylating agents in the ratios of 1:1:2 and 2:1:1, respectively) and symmetrical keto diesters 14 (composed of 2 mol of organozincs and 1 mol of carbon monoxide) are formed in varying ratios depending on the reaction conditions. Synthetic scope of the unsymmetrical ketones and mechanistic rationale for these unique and unprecedented reaction behaviors are discussed.
• Tamaru, Yoshinao; Yasui, Kengo; Takanabe, Hidenobu, Angewandte Chemie, 1992, vol. 104, # 5, p. 662 - 664
  作者：Tamaru, Yoshinao、Yasui, Kengo、Takanabe, Hidenobu、Tanaka, Shuji、Fugami, Keigo

  DOI：——

  日期：——