(E)-5-phenyl-1-(p-tolyl)pent-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)-5-phenyl-1-(p-tolyl)pent-4-en-1-one
• 英文别名: (E)-1-(4-methylphenyl)-5-phenylpent-4-en-1-one
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: WTBLZZKGJFMKIJ-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (2E,4E)-5-phenyl-1-p-tolylpenta-2,4-dien-1-one 在 indium(III) chloride 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以89%的产率得到(E)-5-phenyl-1-(p-tolyl)pent-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。
• <i>Z</i>-Selective Synthesis of γ,δ-Unsaturated Ketones via Pd-Catalyzed Ring Opening of 2-Alkylenecyclobutanones with Arylboronic Acids
  作者：Yao Zhou、Changqing Rao、Qiuling Song

  DOI：10.1021/acs.orglett.6b01816

  日期：2016.8.19

  Pd-catalyzed 1,2-addition (instead of 1,4-addition) of arylboronic acids to 2-alkylenecyclobutanones followed by β-carbon elimination from the resulting palladium cyclobutanolates to afford γ,δ-unsaturated ketones was developed. The desired γ,δ-unsaturated ketones were obtained in good to excellent yields with Z/E selectivities of up to >99:1 and a broad spectrum of functional group tolerability.

  开发了Pd催化的芳基硼酸的1,2-加成（而不是1,4-加成）到2-亚烷基环丁酮，然后从所得的环丁醇钯中消除β-碳，得到γ，δ-不饱和酮。获得了所需的γ，δ-不饱和酮，其收率高至优异，Z / E选择性高达> 99：1，并且具有宽泛的官能团耐受性。
• Ir-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Alkylations
  作者：Hu He、Xiao-Jian Zheng、Yi Li、Li-Xin Dai、Shu-Li You

  DOI：10.1021/ol7019394

  日期：2007.10.1

  [Ir(COD)Cl]2/phosphoramidite ligand 1a was found to be an efficient catalytic system for the highly regio- and enantioselective decarboxylative alkylation of gamma-substituted allyl beta-ketocarboxylates, affording the branched products with up to >99/1 branched-linear ratio and 96% ee.

  发现[Ir（COD）Cl] 2 /亚磷酰胺配体1a是γ-取代的烯丙基β-酮羧酸酯的高度区域和对映选择性脱羧烷基化的有效催化体系，可为支链产物提供最高> 99/1的支链-线性比和96％ee。
• 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.