(Z)-5-iodo-1-phenyl-4-(n-propyl)-4-octen-1-one | 153974-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-5-iodo-1-phenyl-4-(n-propyl)-4-octen-1-one
• CAS: 153974-35-7
• 化学式: C₁₇H₂₃IO
• 分子量: 370.274
• InChiKey: XNTNLWXPMXLLNZ-PEZBUJJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (Z)-5-iodo-1-phenyl-4-(n-propyl)-4-octen-1-one 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 125.0 ℃ 、4.14 MPa 条件下， 反应 20.0h， 生成 (2-Hydroxy-3,4-dipropyl-cyclopenta-1,3-dienyl)-phenyl-methanone 、 5-benzoyl-2,3-di(n-propyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio

  摘要：

  The Pd-catalyzed carbonylative cyclization reaction involving omega-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-O ratio in the trapping with enolates.

  DOI：

  10.1016/s0040-4020(01)80765-1
• 作为产物：
  描述：

  (Z)-5-iodo-1-phenyl-4-(n-propyl)-4-octen-1-ol 在 pyridinium chlorochromate 作用下， 以91%的产率得到(Z)-5-iodo-1-phenyl-4-(n-propyl)-4-octen-1-one
  参考文献：
  名称：

  Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio

  摘要：

  The Pd-catalyzed carbonylative cyclization reaction involving omega-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-O ratio in the trapping with enolates.

  DOI：

  10.1016/s0040-4020(01)80765-1

文献信息

• Catalytic generation and trapping of acylmetals containing Ni and Cu with enolates
  作者：Ei-ichi Negishi、Hidefumi Makabe、Izumi Shimoyama、Guangzhong Wu、Yantao Zhang

  DOI：10.1016/s0040-4020(97)10210-1

  日期：1998.2

  Carbonylative cyclization of iodoarenes and iodoalkenes containing a proximal enolate precursor can selectively provide either cyclic ketones or lactones in the presence of Ni or Cu catalysts via trapping of putative acylmetal derivatives with C-or O-enolates, respectively; the ring size and regioselectivity of the reaction may be predicted based on two generalizations derived from the recently developed corresponding Pd-catalyzed reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.