2-(cyclohex-2-enyl)-1-phenylbutane-1,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(cyclohex-2-enyl)-1-phenylbutane-1,3-dione
• 英文别名: 1,3-diphenyl-2-(2-cyclohexen-1-yl)propane-1,3-dione；2-Cyclohex-2-en-1-yl-1-phenylbutane-1,3-dione；2-cyclohex-2-en-1-yl-1-phenylbutane-1,3-dione
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: PCQAHQVKIUWNAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基-1,3-丁二酮 、 环己烯 在 叔丁基过氧化氢 、 copper(I) bromide 作用下， 以 癸烷 为溶剂， 以64%的产率得到2-(cyclohex-2-enyl)-1-phenylbutane-1,3-dione
  参考文献：
  名称：

  Catalytic Allylic Alkylation via the Cross-Dehydrogenative-Coupling Reaction between Allylic sp³ C−H and Methylenic sp³ C−H Bonds

  摘要：

  A catalytic allylic alkylation was developed via the cross-dehydrogenative-coupling reaction of allylic sp3 C-H and methylenic sp3 C-H catalyzed by copper bromide and cobalt chloride in the presence of an oxidizing reagent, t-BuOOH. This methodology provides a direct way to use allylic sp3 C-H bonds for forming C-C bonds.

  DOI：

  10.1021/ja056541b

文献信息

• Perchloric Acid Catalyzed Homogeneous and Heterogeneous Addition of β-Dicarbonyl Compounds to Alcohols and Alkenes and Investigation of the Mechanism
  作者：Pei Nian Liu、Li Dang、Qing Wei Wang、Shu Lei Zhao、Fei Xia、Yu Jie Ren、Xue Qing Gong、Jun Qin Chen

  DOI：10.1021/jo100517k

  日期：2010.8.6

  The direct addition of various β-dicarbonyl compounds to a series of secondary alcohols and alkenes has been achieved using 1 mol % perchloric acid (HClO4) as the catalyst. The HClO4-catalyzed reactions could be conveniently conducted in commercial solvent and gave moderate to excellent yields. Moreover, the silica gel-supported HClO4 could also catalyze the heterogeneous addition for a series of substrates

  使用1mol％的高氯酸（HClO 4）作为催化剂已经实现了将各种β-二羰基化合物直接添加到一系列仲醇和烯烃中。HClO 4催化的反应可以在商业溶剂中方便地进行，并得到中等至优异的产率。此外，硅胶负载的HClO 4还可以催化一系列底物的均相添加，与均质底物相比，收率相近甚至更高。负载的催化剂可以容易地回收并重复使用四次。此外，研究了HClO 4催化β-二酮加成到醇中的机理，并确定了S N通过一系列实验，第一次明确地证明了一种机理。通过DFT计算还可以合理化区分不同布朗斯台德酸之间的催化能力。
• Catalytic Allylic Alkylation via the Cross-Dehydrogenative-Coupling Reaction between Allylic sp³ C−H and Methylenic sp³ C−H Bonds
  作者：Zhiping Li、Chao-Jun Li

  DOI：10.1021/ja056541b

  日期：2006.1.1

  A catalytic allylic alkylation was developed via the cross-dehydrogenative-coupling reaction of allylic sp3 C-H and methylenic sp3 C-H catalyzed by copper bromide and cobalt chloride in the presence of an oxidizing reagent, t-BuOOH. This methodology provides a direct way to use allylic sp3 C-H bonds for forming C-C bonds.