1-(2-methoxyphenyl)-3-p-tolylpropane-1,3-dione | 41126-23-2

• 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-(2-methoxyphenyl)-3-p-tolylpropane-1,3-dione
• 英文别名: 1-(2-Methoxyphenyl)-3-(4-methylphenyl)propane-1,3-dione
• CAS: 41126-23-2
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: RALISAUPYPYHDG-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±30.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-(2-methoxyphenyl)-3-p-tolylpropane-1,3-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以86%的产率得到2-(4-甲基苯基)-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  K₂CO₃-Catalyzed Synthesis of Chromones and 4-Quinolones through the Cleavage of Aromatic C–O Bonds

  摘要：

  Phenol-derived electrophiles are favorable substrates because phenols are naturally abundant or can be readily prepared from other aromatic compounds. However, the cleavage of aromatic C-O bonds Is a great challenge because of their high energy. K2CO3-catalyzed intramolecular cyclization of 1-(2-alkoxyphenyl)-3-akylpropane-1,3-dlone and 3-(alkylimino)-1-(2-methoxyphenyl)-2-methylpropan-1-one derivatives via the selective cleavage of aromatic C-O bonds Is reported. The corresponding chromone and 4-quinolone derivatives were obtained in reasonable yields.

  DOI：

  10.1021/ol300908g
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 对甲基苯甲酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成 1-(2-methoxyphenyl)-3-p-tolylpropane-1,3-dione
  参考文献：
  名称：

  手性受阻路易斯对催化 1,2-二酮的立体选择性氢化硅烷化

  摘要：

  在受阻路易斯对 (FLP) 催化下，用 PhSiH 3实现不对称邻位二酮的高度立体选择性氢化硅烷化，以高产率生成 1,2-二芳基-1,2-抗二醇，dr 值 >99/1高达 97% ee 。手性FLP催化剂表现出控制区域选择性、非对映选择性和对映选择性的能力，而硅烷PhSiH 3促进第二个羰基的分子内氢化硅烷化。

  DOI：

  10.1002/anie.202313957

文献信息

• Iodine-Catalyzed Synthesis of 1,2-Diaryldiketones by Oxidative Cleavage of 1,3-Diaryldiketones with DMSO
  作者：Yu Yuan、Haitao Zhu

  DOI：10.1002/ejoc.201101028

  日期：2012.1

  A metal-free, efficient, practical, and convenient process based on an iodine-catalyzed oxidative cleavage reaction has been developed to form 1,2-diaryldiketons in high yields from 1,3-diaryldiketones. The reaction is performed in DMSO and in air, and a mechanism was proposed according to the reaction evidence.

  已开发出一种基于碘催化氧化裂解反应的无金属、高效、实用且方便的方法，以从 1,3-二芳基二酮以高产率形成 1,2-二芳基二酮。该反应在DMSO和空气中进行，根据反应证据提出了反应机理。
• nBu4NI-catalyzed C C bond formation to construct 2-carbonyl-1,4-diketones under mild conditions
  作者：Yunhe Lv、Weiya Pu、Jiejie Niu、Qingqing Wang、Qian Chen

  DOI：10.1016/j.tetlet.2018.03.011

  日期：2018.4

  An nBu4NI-catalyzed oxidative cross-dehydrogenative-coupling of β-dicarbonyl compounds with acetone under mild reaction conditions is described. This methodology provides a straightforward pathway to synthesize 2-carbonyl-1,4-diketones and features a simple system, low reaction temperature, and environmental friendliness.

  一个Ñ卜4 NI-催化氧化交脱氢耦合的β二羰基化合物与丙酮在温和的反应条件下进行说明。该方法学提供了合成2-羰基-1,4-二酮的直接途径，并且具有简单的系统，较低的反应温度和环境友好性。
• K₂CO₃-Catalyzed Synthesis of Chromones and 4-Quinolones through the Cleavage of Aromatic C–O Bonds
  作者：Jie Zhao、Yufen Zhao、Hua Fu

  DOI：10.1021/ol300908g

  日期：2012.6.1

  Phenol-derived electrophiles are favorable substrates because phenols are naturally abundant or can be readily prepared from other aromatic compounds. However, the cleavage of aromatic C-O bonds Is a great challenge because of their high energy. K2CO3-catalyzed intramolecular cyclization of 1-(2-alkoxyphenyl)-3-akylpropane-1,3-dlone and 3-(alkylimino)-1-(2-methoxyphenyl)-2-methylpropan-1-one derivatives via the selective cleavage of aromatic C-O bonds Is reported. The corresponding chromone and 4-quinolone derivatives were obtained in reasonable yields.
• Stereoselective Hydrosilylation of 1,2‐Diketones Catalyzed by Chiral Frustrated Lewis Pairs
  作者：Ting Liu、Wei Meng、Xiangqing Feng、Haifeng Du

  DOI：10.1002/anie.202313957

  日期：2024.1.25

  A highly stereoselective hydrosilylation of unsymmetrical vicinal diketones with PhSiH3 was accomplished under the frustrated Lewis pair (FLP) catalysis, delivering 1,2-di-aryl-1,2-anti-diols in high yields with >99/1 dr values and up to 97 % ee. The chiral FLP catalyst exhibits the ability to control regio-, diastereo-, and enantioselectivities, while silane PhSiH3 facilitates an intramolecular hydrosilylation

  在受阻路易斯对 (FLP) 催化下，用 PhSiH 3实现不对称邻位二酮的高度立体选择性氢化硅烷化，以高产率生成 1,2-二芳基-1,2-抗二醇，dr 值 >99/1高达 97% ee 。手性FLP催化剂表现出控制区域选择性、非对映选择性和对映选择性的能力，而硅烷PhSiH 3促进第二个羰基的分子内氢化硅烷化。