1-(3,4-Dichlorophenyl)-5-phenylpenta-2,4-dien-1-one

• 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: 1-(3,4-Dichlorophenyl)-5-phenylpenta-2,4-dien-1-one
• 化学式: C₁₇H₁₂Cl₂O
• 分子量: 303.188
• InChiKey: XKSJWAFDROAGJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,4-Dichlorophenyl)-5-phenylpenta-2,4-dien-1-one 在 甲酸铵 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以65%的产率得到2-(3,4-dichlorophenyl)-6-phenylpyridine
  参考文献：
  名称：

  线性的α，β，γ，δ-不饱和酮通过加成铵和随后的环化反应合成不对称的2,6-二芳基吡啶

  摘要：

  纪念张永民教授（1932-2019） 抽象的 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。

  DOI：

  10.1055/s-0037-1610725
• 作为产物：
  描述：

  2-溴-3',4'-二氯苯乙酮 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 1-(3,4-Dichlorophenyl)-5-phenylpenta-2,4-dien-1-one
  参考文献：
  名称：

  Asymmetric 1,4-Conjugate Addition of Diarylphosphines to α,β,γ,δ-Unsaturated Ketones Catalyzed by Transition-Metal Pincer Complexes

  摘要：

  An enantioselective asymmetric 1,4-addition of diarylphosphines to linear alpha,beta,gamma,delta-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an alpha,beta,gamma,delta-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.

  DOI：

  10.1021/acs.organomet.5b00787

文献信息

• Bhat, K. Ishwar; Kumar, Abhishek; Prathyusha, Indian Journal of Heterocyclic Chemistry, 2015, vol. 25, # 2, p. 161 - 164
  作者：Bhat, K. Ishwar、Kumar, Abhishek、Prathyusha

  DOI：——

  日期：——
• Asymmetric 1,4-Conjugate Addition of Diarylphosphines to α,β,γ,δ-Unsaturated Ketones Catalyzed by Transition-Metal Pincer Complexes
  作者：Xiang-Yuan Yang、Wee Shan Tay、Yongxin Li、Sumod A. Pullarkat、Pak-Hing Leung

  DOI：10.1021/acs.organomet.5b00787

  日期：2015.10.26

  An enantioselective asymmetric 1,4-addition of diarylphosphines to linear alpha,beta,gamma,delta-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an alpha,beta,gamma,delta-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.
• Synthesis of Asymmetrical 2,6-Diarylpyridines from Linear α,β,γ,δ-Unsaturated Ketones by Addition of Ammonium Formate Followed by Annulation
  作者：Yejun Gao、Rener Chen、Yongmin Ma

  DOI：10.1055/s-0037-1610725

  日期：2019.10

  established for the synthesis of asymmetrical 2,6-diarylpyridines by cyclization of α,β,γ,δ-unsaturated ketones with ammonium formate under air atmosphere. The reaction is metal-free and operationally convenient from readily available starting materials. Thirty-three examples have been presented, most of which show good yields. A simple and efficient method has been established for the synthesis of asymmetrical

  纪念张永民教授（1932-2019） 抽象的 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。 建立了一种简单有效的方法，通过在空气气氛下用甲酸铵将α，β，γ，δ-不饱和酮环化来合成不对称的2,6-二芳基吡啶。该反应是无金属的，并且易于获得的起始原料在操作上是方便的。已经提出了33个例子，其中大多数显示出良好的产量。