1,3-bis(2-methylphenyl)-2-butene-1-one | 84118-71-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-bis(2-methylphenyl)-2-butene-1-one
• 英文别名: 2,2′-dimethyldypnone；1,3-Bis(2-methylphenyl)but-2-en-1-one
• CAS: 84118-71-8
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: OYHYMUOTOFEWJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-bis(2-methylphenyl)-2-butene-1-one 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 12.0h， 以54%的产率得到1,3,5-三(2-甲基苯基)苯
  参考文献：
  名称：

  Rearrangement of Dypnones to 1,3,5-Triarylbenzenes

  摘要：

  Rearrangement of dypnones to 1,3,5-triarylbenzenes is described. The reaction is proposed to involve an aldol-type self-condensation of dypnones, followed by an intramolecular [2 + 2] cycloaddition and a retro-[2 + 2] cycloaddition. The reaction goes smoothly under obviously milder conditions in comparison to the cyclotrimerization of acetophenones to 1,3,5-triarylbenzenes (10 mol % of TsOH, 80 degrees C versus 130-148 degrees C). This unexpected rearrangement would provide new possible considerations in dypnone-involved organic synthesis.

  DOI：

  10.1021/acs.orglett.5b00353
• 作为产物：
  描述：

  2-碘代甲苯 生成 1,3-bis(2-methylphenyl)-2-butene-1-one
  参考文献：
  名称：

  Palladium-catalyzed acylation of unsaturated halides by anions of enol ethers

  摘要：

  DOI：

  10.1021/ja00342a050

文献信息

• Synthesis of conjugated dienes and polyenes via diethyl phosphite promoted carbonyl olefination
  作者：Ru Wang、Songlin Zhang

  DOI：10.1039/c4ra06256f

  日期：——

  A protocol has been developed for the synthesis of conjugated dienes and polyenes from unsaturated carbonyl compounds and Grignard reagents in the presence of diethyl phosphite. This reaction was conveniently carried out under mild conditions in a one-pot fashion with moderate to good yields.

  已经开发了在亚磷酸二乙酯存在下由不饱和羰基化合物和格氏试剂合成共轭二烯和多烯的方案。该反应方便地在温和条件下以一锅法以中等至良好的产率进行。
• Carboxylative cyclization of substituted propenyl ketones using CO₂: transition-metal-free synthesis of α-pyrones
  作者：Wen-Zhen Zhang、Ming-Wang Yang、Xiao-Bing Lu

  DOI：10.1039/c6gc01346e

  日期：——

  Carbon dioxide is a green carboxylative reagent with regard to its non-toxic and renewable property. Described herein is a carboxylative cyclization of substituted 1-propenyl ketones via [gamma]-carboxylation using CO2, which...

  就其无毒和可再生的特性而言，二氧化碳是一种绿色的羧化试剂。本文描述了使用CO 2通过γ-羧化作用的取代的1-丙烯基酮的羧基化环化反应，...
• Sodium-Catalyzed Reactions of o-, m- and p-Methylstyrene in the Presence of Toluene^1,2
  作者：HERMAN PINES、JOSEPH SHABTAI

  DOI：10.1021/jo01069a011

  日期：1961.11
• Palladium-catalyzed acylation of unsaturated halides by anions of enol ethers
  作者：Charles E. Russell、Louis S. Hegedus

  DOI：10.1021/ja00342a050

  日期：1983.2
• Rearrangement of Dypnones to 1,3,5-Triarylbenzenes
  作者：Kai Deng、Qi-Yong Huai、Zhi-Lun Shen、Hui-Jing Li、Chen Liu、Yan-Chao Wu

  DOI：10.1021/acs.orglett.5b00353

  日期：2015.3.20

  Rearrangement of dypnones to 1,3,5-triarylbenzenes is described. The reaction is proposed to involve an aldol-type self-condensation of dypnones, followed by an intramolecular [2 + 2] cycloaddition and a retro-[2 + 2] cycloaddition. The reaction goes smoothly under obviously milder conditions in comparison to the cyclotrimerization of acetophenones to 1,3,5-triarylbenzenes (10 mol % of TsOH, 80 degrees C versus 130-148 degrees C). This unexpected rearrangement would provide new possible considerations in dypnone-involved organic synthesis.