2,3-二溴-1-苯基-1,4-戊二酮 | 181627-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,3-二溴-1-苯基-1,4-戊二酮
• 英文名称: 2,3-dibromo-1-phenyl-1,4-pentanedione
• 英文别名: 2,3-Dibromo-1-phenylpentane-1,4-dione；2,3-dibromo-1-phenylpentane-1,4-dione
• CAS: 181627-65-6
• 化学式: C₁₁H₁₀Br₂O₂
• 分子量: 334.007
• InChiKey: MXQSWCGYFLFJOK-UHFFFAOYSA-N

物化性质

• 沸点：
  380.5±42.0 °C(Predicted)
• 密度：
  1.715±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2,3-二溴-1-苯基-1,4-戊二酮 在 sodium tetrahydroborate 、 三溴化锑 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以84%的产率得到1-苯基-1,4-戊二酮
  参考文献：
  名称：

  NaBH4-SbBr3还原α-卤代羰基化合物

  摘要：

  发现试剂 NaBH4-SbBr3 对芳香族 α-溴羰基化合物和 2,3-二溴-1,4-丁二酮的还原脱溴具有化学选择性。

  DOI：

  10.1246/cl.1996.633
• 作为产物：
  描述：

  1-phenyl-2-penten-1,4-dione 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 生成 2,3-二溴-1-苯基-1,4-戊二酮
  参考文献：
  名称：

  [3 + 2] Annulation of Allylidenetriphenylphosphorane with 1,2-Diacylethylenes and 1,2-Diacylacetylenes:  A One-Step Synthesis of Tri- and Tetrasubstituted Cyclopentadienes and Fulvenes

  摘要：

  Allylidenetriphenylphosphoranes underwent [3 + 2] annulation with 1,2-diacylethylenes at room temperature to give cyclopentadienes 11-17 having various substituents except for (Z)-3-acetylacrolein (18) which gave cyclohexadiene 19 derived from [3 + 3] annulation as the sole annulation product. The resulting cyclopentadienes were mixtures of the corresponding double-bond isomers which arose through an equilibrium process from the initially formed 1,3-dienes a under the weakly basic reaction conditions. Similar reactions of the phosphoranes with 1,2-diacylacetylenes afforded substituted fulvenes 24, 25, and 28 directly without the attendant formation of the corresponding benzene derivatives which come from another possible [3 + 3] annulation. The observed high level of the preference for the [3 + 2] annulation is discussed on the basis of the semiempirical PM3 MO calculations. The calculations suggested that the course of the annulation may be kinetically controlled at the oxaphosphetane-forming step of the intramolecular Wittig reaction.

  DOI：

  10.1021/jo970594x

文献信息

• Reduction of<i>α</i>-Halo Carbonyl Compounds with NaBH₄-SbBr₃
  作者：Shinsei Sayama、Yutaka Inamura

  DOI：10.1246/cl.1996.633

  日期：1996.8

  The reagent NaBH4-SbBr3 was found to be chemoselective for the reductive debromination of aromatic α-bromo carbonyl compounds and 2,3-dibromo-1,4-butanediones.

  发现试剂 NaBH4-SbBr3 对芳香族 α-溴羰基化合物和 2,3-二溴-1,4-丁二酮的还原脱溴具有化学选择性。
• [3 + 2] Annulation of Allylidenetriphenylphosphorane with 1,2-Diacylethylenes and 1,2-Diacylacetylenes:  A One-Step Synthesis of Tri- and Tetrasubstituted Cyclopentadienes and Fulvenes
  作者：Yuichiro Himeda、Hiroshi Yamataka、Ikuo Ueda、Minoru Hatanaka

  DOI：10.1021/jo970594x

  日期：1997.9.1

  Allylidenetriphenylphosphoranes underwent [3 + 2] annulation with 1,2-diacylethylenes at room temperature to give cyclopentadienes 11-17 having various substituents except for (Z)-3-acetylacrolein (18) which gave cyclohexadiene 19 derived from [3 + 3] annulation as the sole annulation product. The resulting cyclopentadienes were mixtures of the corresponding double-bond isomers which arose through an equilibrium process from the initially formed 1,3-dienes a under the weakly basic reaction conditions. Similar reactions of the phosphoranes with 1,2-diacylacetylenes afforded substituted fulvenes 24, 25, and 28 directly without the attendant formation of the corresponding benzene derivatives which come from another possible [3 + 3] annulation. The observed high level of the preference for the [3 + 2] annulation is discussed on the basis of the semiempirical PM3 MO calculations. The calculations suggested that the course of the annulation may be kinetically controlled at the oxaphosphetane-forming step of the intramolecular Wittig reaction.