3-(4-chlorophenyl)-1,5-diphenyl-1,5-pentanedione | 107969-75-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-(4-chlorophenyl)-1,5-diphenyl-1,5-pentanedione
• 英文别名: 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione；3-(p-chlorophenyl)-1,5-diphenyl-1,5-pentanedione；3-(p-chlorophenyl)-1,5-diphenylpentane-1,5-dione；3-(4-chloro-phenyl)-1,5-diphenyl-pentane-1,5-dione；3-(4-Chlor-phenyl)-1,5-diphenyl-pentan-1,5-dion
• CAS: 107969-75-5
• 化学式: C₂₃H₁₉ClO₂
• 分子量: 362.856
• InChiKey: XYSHVVOXHFAUOV-UHFFFAOYSA-N

物化性质

• 熔点：
  109.5-110.5 °C
• 沸点：
  533.9±50.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-1,5-diphenyl-1,5-pentanedione 在 乙醇 、 盐酸羟胺 作用下， 生成 4-(4-氯苯基)-2,6-二苯基吡啶
  参考文献：
  名称：

  Pyridines. IV. A Study of the Chichibabin Synthesis

  摘要：

  DOI：

  10.1021/ja01176a008
• 作为产物：
  描述：

  4-氯查耳酮 在 copper(l) iodide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以65%的产率得到3-(4-chlorophenyl)-1,5-diphenyl-1,5-pentanedione
  参考文献：
  名称：

  Copper-catalyzed synthesis of 1,3,5-triarylpentane-1,5-diones from α,β-unsaturated ketones

  摘要：

  使用α，β-不饱和酮作为独特的起始物质，描述了一种高效的铜催化合成1,3,5-三芳基戊二酮的方法。

  DOI：

  10.1039/c5ra09155a

文献信息

• Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN
  作者：Muthupandi Nagaraj、Muthusamy Boominathan、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c1ob05232b

  日期：——

  simple and efficient protocol for the construction of substituted piperazines, piperidines, thiomorpholines, decahydroquinolines, perhydrocyclopenta[b]pyridine, and pyrrolidines bearing N-hydroxy substituents through intramolecular reductive cyclization of diketoximes using sodium cyanoborohydride is described.

  描述了使用氰基硼氢化钠通过二酮肟的分子内还原环化反应来构建带有N-羟基取代基的取代哌嗪，哌啶，硫吗啉，十氢喹啉，全氢环戊[b]吡啶和吡咯烷的简单有效的方法。
• Lipase-Catalysed Addition of Pyrrolidine to Chalcone and Benzylidene Malonate Derivatives
  作者：Z. Habibi、M. Yousefi、R. Kheyrabadi、M. Mohammadi、M. Moemeni、S. Nazari

  DOI：10.1007/s10600-015-1434-1

  日期：2015.9

  The porcine pancreas lipase (PPL) type II catalyzes the aminolysis of benzylidene malonates by regiospecific amidation of substrates and afforded the Z-isomer; no E-isomer or diamide byproducts were observed. PPL also catalyzes Michael addition of acetophenone to various derivatives of chalcones.

  猪胰脂肪酶II型（PPL）特异性地催化苯亚甲基丙二酸酯的酰胺解反应，生成Z-异构体；未观察到E-异构体或双酰胺副产物。PPL还能催化乙酰苯与查尔酮的各种衍生物发生迈克尔加成反应。
• Esterification, Etherification, and Aldol Condensation Using Cathodically-Generated Organic Olate Anions
  作者：Toshio Fuchigami、Takeshi Awata、Tsutomu Nonaka、Manuel M. Baizer

  DOI：10.1246/bcsj.59.2873

  日期：1986.9

  Cathodic methods for the esterification of carboxylic acids and the etherification of phenol and benzenethiol under mild conditions were developed. The esterification was successfully carried out at room temperature by the reaction of alkylating reagents with cathodically-generated quaternary ammonium carboxylates. The etherification was similarly achieved using electrogenerated quaternary ammonium phenolate and halonitrobenzenes. A hindered phenolate anion cathodically-generated from 2,6-di-t-butyl-p-cresol remarkably promoted aldol condensation of aromatic ketones and aldehydes, and allowed subsequent Michael reaction to provide efficiently symmetrical 1,5-diketones.

  开发了在温和条件下对羧酸酯化和苯酚及苯硫醇醚化的阴极法。通过烷基化试剂与阴极生成的季铵羧酸盐的反应，酯化成功地在室温下进行。醚化则采用了电生成的季铵苯醇盐和卤代硝基苯。由2,6-二叔丁基-p-甲酚阴极生成的阻碍性苯醇阴离子显著促进了芳香酮和醛的 aldol 缩合，并允许后续的迈克尔反应，高效提供对称的1,5-二酮。
• In situ formed acetals facilitated direct Michael addition of unactivated ketones
  作者：Srinivasa Rao Koppolu、Rengarajan Balamurugan

  DOI：10.1039/c6nj02954j

  日期：——

  TfOH-promoted synthesis of 1,5-diketones by the Michael reaction of unactivated ketones with chalcones has been described. Acetals formed under HC(OMe)3/TfOH conditions generate the required enol-equivalents for a smooth Michael reaction. A wide array of symmetrical and unsymmetrical 1,5-diketones has been synthesised.

  已经描述了通过未活化的酮与查耳酮的迈克尔反应，TfOH促进的1，5-二酮的合成。在HC（OMe）3 / TfOH条件下形成的缩醛生成所需的烯醇当量，以使迈克尔反应平稳。已经合成了各种各样的对称和不对称的1，5-二酮。
• Unexpected synthesis of 1,3,5-triarly-1,5-diketones from aryl ketones via di-enamine mechanism
  作者：Bin Liu、Junfeng Wang、Yi Pang、Zemei Ge、Runtao Li

  DOI：10.1016/j.tet.2014.10.009

  日期：2014.12

  An unexpected reaction of aryl ketone with acetohydrazone of aromatic aldehyde via 1,2-di-enamine/di-iminium mechanism was discovered, leading to efficient synthesis of 1,3,5-triaryl-1,5-diketones in good to excellent yields.

  发现芳基酮与芳香醛的乙酰nium通过1,2-二烯胺/二亚胺机理的意外反应，导致1,3,5-三芳基-1,5-二酮的高效合成，收率良好。