2-(4-Methylphenyl)-3-oxo-3-phenylpropanal | 93633-29-5

• 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-Methylphenyl)-3-oxo-3-phenylpropanal
• CAS: 93633-29-5
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: IBHGBLIBLAOHAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-Methylphenyl)-3-oxo-3-phenylpropanal 在 1,3-二甲基-2-苯基-2H-苯并咪唑 、 甲烷磺酸 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以53%的产率得到1-phenyl-2-(p-tolyl)prop-2-en-1-one
  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
• 作为产物：
  描述：

  1-phenyl-3-(p-methylphenyl)-2,3-epoxy-1-propanone 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(4-Methylphenyl)-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

• A novel Friedlander-type synthesis of 3-aryl quinolines from 3-oxo-2,3-diaryl-propionaldehydes
  作者：Wanrong Luo、Qiuchao Mu、Wenwei Qiu、Ting Liu、Fan Yang、Xiaofeng Liu、Jie Tang

  DOI：10.1016/j.tet.2011.07.004

  日期：2011.9

  3-Aryl quinolines are readily synthesized by a novel Friedlander-type reaction with 3-oxo-2,3-diaryl-propionaldehydes and 2-amino arylaldehydes. A preliminary mechanism of this novel one pot, two-step synthesis has been explored with the proofs of isolation of the enaminone intermediate and the eliminated benzoic acid in this reaction. (C) 2011 Elsevier Ltd. All rights reserved.
• Selective Cα-O bond cleavage of chalcone epoxides induced by pyrylium salt sensitized photoreactions and dark reactions with cerium(iv) salts
  作者：Eietsu Hasegawa、Kenyuki Ishiyama、Hiroki Kashiwazaki、Takaaki Horaguchi、Takahachi Shimizu

  DOI：10.1016/s0040-4039(00)94495-2

  日期：1990.1
• HASEGAWA, EIETSU;ISHIYAMA, KENYUKI;KASHIWAZAKI, HIROKI;HORAGUCHI, TAKAAKI+, TETRAHDERON. LETT., 31,(1990) N8, C. 4045-4048
  作者：HASEGAWA, EIETSU、ISHIYAMA, KENYUKI、KASHIWAZAKI, HIROKI、HORAGUCHI, TAKAAKI+

  DOI：——

  日期：——
• 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.