(E)-1-(4’-chlorophenyl)-5-phenylpent-4-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(4’-chlorophenyl)-5-phenylpent-4-en-1-one
• 英文别名: (E)-1-(4-chlorophenyl)-5-phenylpent-4-en-1-one；1-(4'-chlorophenyl)-5-phenylpent-4-en-1-one
• 化学式: C₁₇H₁₅ClO
• 分子量: 270.758
• InChiKey: WHZNLOAWRZLLDC-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)-5-苯基-2,4-戊二烯-1-酮 在 indium(III) chloride 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以89%的产率得到(E)-1-(4’-chlorophenyl)-5-phenylpent-4-en-1-one
  参考文献：
  名称：

  Remarkably Selective Reduction of the α,β-Carbon−Carbon Double Bond in Highly Activated α,β,γ,δ-Unsaturated Alkenes by the InCl₃−NaBH₄ Reagent System

  摘要：

  A combination of sodium borohydride and a catalytic amount of indium(III) chloride in acetonitrile reduces exclusively the alpha,beta-carbon-carbon double bond in alpha,beta,gamma,delta-unsaturated diaryl ketones, dicarboxylic ester, cyano-ester, and dicyano compounds.

  DOI：

  10.1021/jo0347821

文献信息

• Palladium-catalyzed carbonylative/decarboxylative cross-coupling of α-bromo-ketones with allylic alcohols to γ,δ-unsaturated ketones
  作者：Jin-Bao Peng、Le-Cheng Wang、Xiao-Feng Wu

  DOI：10.1016/j.tetlet.2019.150991

  日期：2019.8

  In this communication, a palladium-catalyzed carbonylative/decarboxylative cross-coupling of α-bromo-ketones with allylic alcohols has been developed. With Mo(CO)6 as the CO source, γ,δ-unsaturated ketones were isolated in good yields. The release of CO2 was confirmed as well.

  在这种交流中，已经开发出钯催化的α-溴酮与烯丙基醇的羰基/脱羧交叉偶联。以Mo（CO）6为一氧化碳源，可以很好地分离出γ，δ-不饱和酮。还确认了CO 2的释放。
• Formation of C(sp³)–C(sp³) Bonds by Palladium Catalyzed Cross-Coupling of α-Diazoketones and Allylboronic Acids
  作者：Marie-Charlotte Belhomme、Dong Wang、Kálmán J. Szabó

  DOI：10.1021/acs.orglett.6b01132

  日期：2016.5.20

  Palladium catalyzed cross-coupling of allylboronic acids with a-diazoketones was studied. The reaction selectively affords the linear allylic product. The reaction proceeds with formation of a new C(sp(3))-C(sp(3)) bond. The reaction was performed without an external oxidant, likely without the Pd-catalyst undergoing redox reactions.
• Remarkably Selective Reduction of the α,β-Carbon−Carbon Double Bond in Highly Activated α,β,γ,δ-Unsaturated Alkenes by the InCl₃−NaBH₄ Reagent System
  作者：Brindaban C. Ranu、Sampak Samanta

  DOI：10.1021/jo0347821

  日期：2003.9.1

  A combination of sodium borohydride and a catalytic amount of indium(III) chloride in acetonitrile reduces exclusively the alpha,beta-carbon-carbon double bond in alpha,beta,gamma,delta-unsaturated diaryl ketones, dicarboxylic ester, cyano-ester, and dicyano compounds.