2-(4-chlorophenyl)-3-oxo-3-phenylpropanal

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-chlorophenyl)-3-oxo-3-phenylpropanal
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: OTWYMXLUEXOXRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-(4-chlorophenyl)-3-oxo-3-phenylpropanal 在 乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到2-(4-氯苯基)-1-苯乙酮
  参考文献：
  名称：

  从查耳酮高效合成脱氧安息香

  摘要：

  摘要 通过路易斯酸催化重排由查耳酮环氧化物衍生的 β-酮醛在乙二胺存在下在四氢呋喃 (THF) 中回流时发生平稳的去甲酰化反应，以优异的产率得到脱氧安息香。该方法是通用的，可用于制备具有多种取代模式的脱氧安息香。

  DOI：

  10.1080/00397910601130967
• 作为产物：
  描述：

  4-氯查耳酮 在 三氟化硼乙醚 、 双氧水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(4-chlorophenyl)-3-oxo-3-phenylpropanal
  参考文献：
  名称：

  Metal-Free, One-Pot, Sequential Protocol for Transforming α,β-Epoxy Ketones to β-Hydroxy Ketones and α-Methylene Ketones

  摘要：

  A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to beta-hydroxy ketones and alpha-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluoride etherate ((BF3OEt2)-O-.) generates the cationic intermediates by regioselective epoxide ring opening and an acyl shift. Then, a treatment of these cations with 2-aryl-1,3-dimethylbenzimidazolines (DMBIH) results in formation of 1,2-disubstituted 3-hydroxy ketones. DMBIH serves as a hydride donor in the second step of this process. Finally, the beta-hydroxy ketones can be converted to 1,2-disubstituted 2-methylene ketones by treatment with methanesulfonic acid or a combination of methanesulfonyl chloride and triethylamine. Importantly, the sequential steps involved in formation of the alpha-methylene ketone products can be carried out in one pot.

  DOI：

  10.1021/jo5025249

文献信息

• Metal-Free, One-Pot, Sequential Protocol for Transforming α,β-Epoxy Ketones to β-Hydroxy Ketones and α-Methylene Ketones
  作者：Eietsu Hasegawa、Saki Arai、Eiji Tayama、Hajime Iwamoto

  DOI：10.1021/jo5025249

  日期：2015.2.6

  A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to beta-hydroxy ketones and alpha-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluoride etherate ((BF3OEt2)-O-.) generates the cationic intermediates by regioselective epoxide ring opening and an acyl shift. Then, a treatment of these cations with 2-aryl-1,3-dimethylbenzimidazolines (DMBIH) results in formation of 1,2-disubstituted 3-hydroxy ketones. DMBIH serves as a hydride donor in the second step of this process. Finally, the beta-hydroxy ketones can be converted to 1,2-disubstituted 2-methylene ketones by treatment with methanesulfonic acid or a combination of methanesulfonyl chloride and triethylamine. Importantly, the sequential steps involved in formation of the alpha-methylene ketone products can be carried out in one pot.
• Efficient Synthesis of Deoxybenzoins from Chalcones
  作者：Paulson Mathew、Daliya Mathew、C. V. Asokan

  DOI：10.1080/00397910601130967

  日期：2007.3

  Abstract β‐Ketoaldehydes derived from chalcone epoxides by Lewis acid–catalyzed rearrangement underwent smooth deformylation when refluxed in tetrahydrofuran (THF) in the presence of ethylenediamine, affording deoxybenzoins in excellent yields. The method is general and useful for the preparation of deoxybenzoins with a variety of substitution patterns.

  摘要 通过路易斯酸催化重排由查耳酮环氧化物衍生的 β-酮醛在乙二胺存在下在四氢呋喃 (THF) 中回流时发生平稳的去甲酰化反应，以优异的产率得到脱氧安息香。该方法是通用的，可用于制备具有多种取代模式的脱氧安息香。