3-(4-methoxyphenyl)-3-oxo-2-phenylpropanal | 93011-61-1

• 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: 3-(4-methoxyphenyl)-3-oxo-2-phenylpropanal
• 英文别名: 3-oxo-2-phenyl-3-(4-methoxyphenyl)propanal；Phenyl-p-anisoyl-acetaldehyd；3-(4-methoxy-phenyl)-3-oxo-2-phenyl-propionaldehyde
• CAS: 93011-61-1
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: COFNQGBTKBWQBW-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84 °C
• 沸点：
  425.5±35.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-3-oxo-2-phenylpropanal 在 盐酸 、 乙醇 、 羟胺 、 sodium ethanolate 作用下， 生成 3-(4-methoxyphenyl)-3-oxo-2-phenylpropanenitrile
  参考文献：
  名称：

  Takagi; Yasuda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 467,469

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 3-(4-methoxyphenyl)-3-oxo-2-phenylpropanal
  参考文献：
  名称：

  Algar; McKenna, Proceedings of the Royal Irish Academy. Section B: Biological, geological, and chemical science, 1944, vol. 49B, p. 225,236

  摘要：

  DOI：

文献信息

• Highly chemo- and regioselective rearrangement of α,β-epoxy ketones to 1,3-dicarbonyl compounds in 5 mol dm−3 lithium perchlorate–diethyl ether medium
  作者：S. Sankararaman、J. E. Nesakumar

  DOI：10.1039/a905619j

  日期：——

  Epoxides from α,β-unsaturated ketones undergo highly chemo- and regioselective rearrangement to 1,3-dicarbonyl compounds in 5 mol dm–3 lithium perchlorate–diethyl ether medium by a 1,2-migration of the carbonyl group at ambient conditions.

  从α环氧化物，β不饱和酮经历高度化疗和区域选择性重排1,3-二羰基化合物中的5摩尔分米-3通过羰基的在环境条件下的1,2-迁移高氯酸锂-乙醚平台。
• A high‐yielding protocol for the synthesis of 4, <scp>5‐diarylpyrimidin</scp> ‐2‐amine derivatives from chalcones
  作者：Krishnaraj Kooramatom Unni、Prasanth K. Menon、Scholly Clair George、Sajesh P. Thomas、K. S. Devaky

  DOI：10.1002/jhet.4369

  日期：2022.1

  A novel, high yielding and versatile protocol was achieved for the synthesis of 4,5-diaryl-2-pyrimidinamine derivatives from chalcones. The synthesis was accomplished by converting the chalcones into 3-chloro-2,3-diaryl-2-propen-1-ones followed by subsequent reaction with amidine derivatives.

  从查尔酮合成 4,5-diaryl-2-pyrimidinamine 衍生物，实现了一种新颖、高产和通用的方案。该合成是通过将查尔酮转化为 3-氯-2,3-二芳基-2-丙烯-1-酮，然后与脒衍生物反应来完成的。
• 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。
• 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.
• 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.