2-phenyl-2-(4'-methoxyphenyl)-4'-methoxyacetophenone | 26215-78-1

• 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: 2-phenyl-2-(4'-methoxyphenyl)-4'-methoxyacetophenone
• 英文别名: 2-(p-methoxyphenyl)-2-phenyl-4'-methoxyacetophenone；1,2-Dianisyl-2-phenylethanon；1,2-Bis(4-methoxyphenyl)-2-phenylethanone
• CAS: 26215-78-1
• 化学式: C₂₂H₂₀O₃
• 分子量: 332.399
• InChiKey: OZZIFFFOZYWNDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  邻苯二甲醚 、 2-phenyl-2-(4'-methoxyphenyl)-4'-methoxyacetophenone 在 dipotassium peroxodisulfate 、 三氟乙酸 作用下， 反应 24.0h， 以69%的产率得到2-(3,4-dimethoxyphenyl)-1,2-bis(4-methoxyphenyl)-2-phenylethanone
  参考文献：
  名称：

  通过三级sp3 C的好氧脱氢α-芳基化反应选择性合成苯并品酸。1,1-二苯甲酮与芳族和杂芳族化合物的氢键

  摘要：

  通过有氧脱氢α对称和不对称benzopinacolones的区域选择性合成-芳基化在第三SP 3 Ç 取代的1,1- diphenylketones与芳族和杂芳族化合物的H键，在K的存在2 š 2 ö 8在CF 3 COOH描述在室温下。该反应通过提出碳阳离子中间体，该中间体可直接从SP的断裂而产生的去3 Ç  ħ1,1-二苯甲酮的结合。随后的α -芳基化是在亚甲基SP达到3取代酮的碳原子。多种取代的芳族和杂芳族化合物与该反应相容。此外，苯并频哪酮被转化为空间受阻的四取代烯烃和多环芳族化合物。

  DOI：

  10.1002/chem.201404308
• 作为产物：
  描述：

  2,2-bis(p-methoxyphenyl)-1-phenylvinyl bromide 生成 2-phenyl-2-(4'-methoxyphenyl)-4'-methoxyacetophenone
  参考文献：
  名称：

  Rappoport,Z.; Houminer,Y., Journal of the Chemical Society. Perkin transactions II, 1973, p. 1506 - 1518

  摘要：

  DOI：

文献信息

• Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls
  作者：Shengfei Jin、Hang T. Dang、Graham C. Haug、Viet D. Nguyen、Hadi D. Arman、Oleg V. Larionov

  DOI：10.1039/d0sc03118f

  日期：——

  challenging but synthetically indispensable approach to α-branched carbonyl motifs that are widely represented among drugs, natural products, and synthetic intermediates. Here, we describe a simple approach to generation of boron enolates in the absence of strong bases that allows for introduction of both α-alkyl and α-aryl groups in a reaction of readily accessible 1,2-dicarbonyls and organoboranes. Obviation

  在α-碳上构建CC键是一种具有挑战性但在合成中必不可少的方法，可用于药物，天然产物和合成中间体中的α-支链羰基。在这里，我们描述了一种在不存在强碱的情况下生成烯醇硼的简单方法，该方法允许在易于获得的1,2-二羰基与有机硼烷的反应中引入α-烷基和α-芳基。避免使用非选择性，强碱性和亲核试剂，可以在亲电体存在的情况下进行反应，亲电体会拦截中间的硼烯醇化物，从而在三组分过程中产生两个新的α-C-C键。
• Intermolecular and Intramolecular Ketone–Nitrile Reductive Coupling Reactions Promoted by TiCl4–Sm System
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1016/s0040-4020(00)00077-6

  日期：2000.5

  The intermolecular and intramolecular reductive coupling reactions of ketones with nitriles have been successfully promoted by low-valent titanium prepared by the TiCl4-Sm system. Substituted ketones, monocyclic alpha-amino alcohols and monocyclic amines composed of a number of substitution patterns have been prepared in good yields at room or THF reflux temperature under neutral conditions. The procedure can avoid over reduction of the resulting of ketones, alpha-amino alcohols or amines. The crystal structures of two monocyclic alpha-amino alcohols are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Ipso substitution of triarylvinyl cations by alkoxide anions
  作者：Tsugio Kitamura、Takashi Kabashima、Ichizo Nakamura、Tetsuro Fukuda、Hiroshi Taniguchi

  DOI：10.1021/ja00019a025

  日期：1991.9

  Photolysis and solvolysis of triarylbromoethanes 1 in the presence of alkoxide anions in alcohols resulted in significant formation of products derived from ipso substitution by alkoxide anions. Photolysis of 1-aryl-1-bromo-2,2-diphenylethenes 1Aa and 1Ab with 10 mol equiv of alkoxide anions gave 1-alkoxy-1-aryl-2,2-diphenylethenes 2A and 3,3-dialkoxy-6-(2,2-diphenylvinylidene)-1,4-cyclohexadienes 3A (ipso adducts). However, the photolysis with weak bases such as TEA, pyridine, NaHCO3, and K2CO3 did not give ipso adducts 3A but only enol ethers 2A. Interestingly, photolysis of 2,2-bis(p-alkoxyphenyl)-1-bromo-1-phenylethenes 4a and 4b with NaOEt in ethanol afforded ipso adducts 6a and 6b, respectively, which had a 1,2-aryl-rearranged structure. Furthermore, solvolysis of 1-bromo-1-(p-methoxyphenyl)ethenes 1Aa, 1Ba, and 1Ca in ethanol containing 10 mol equiv of NaOEt at 120-130-degrees-C for 1-3 days provided p-ethoxyphenyl-substituted enol ethers 2bb, p-ethoxyphenyl-substituted bromoethenes 1b, and p-methoxyphenyl-substituted enol ethers 2ab, respectively. The major formation of p-ethoxyphenyl-substituted compounds (ipso-substituted products) suggests that there is no large difference in ipso substitution between vinyl cations generated by photolysis and solvolysis. On the basis of the results obtained above the factors affecting ipso attack on arylvinyl cations are discussed.
• Papillon-Jegou,D. et al., Bulletin de la Societe Chimique de France, 1978, vol. <II>, p. 234 - 240
  作者：Papillon-Jegou,D. et al.

  DOI：——

  日期：——
• A Regioselective Synthesis of Benzopinacolones through Aerobic Dehydrogenative α-Arylation of the Tertiary sp³CH Bond of 1,1-Diphenylketones with Aromatic and Heteroaromatic Compounds
  作者：Nagnath Yadav More、Masilamani Jeganmohan

  DOI：10.1002/chem.201404308

  日期：2015.1.12

  1‐diphenylketone. Subsequent α‐arylation was achieved at the methene sp3 carbon atom of the substituted ketone. A variety of substituted aromatic and heteroaromatic compounds were compatible with this reaction. In addition, benzopinacolones were converted into sterically hindered, tetrasubstituted alkenes and polycyclic aromatic compounds.

  通过有氧脱氢α对称和不对称benzopinacolones的区域选择性合成-芳基化在第三SP 3 Ç 取代的1,1- diphenylketones与芳族和杂芳族化合物的H键，在K的存在2 š 2 ö 8在CF 3 COOH描述在室温下。该反应通过提出碳阳离子中间体，该中间体可直接从SP的断裂而产生的去3 Ç  ħ1,1-二苯甲酮的结合。随后的α -芳基化是在亚甲基SP达到3取代酮的碳原子。多种取代的芳族和杂芳族化合物与该反应相容。此外，苯并频哪酮被转化为空间受阻的四取代烯烃和多环芳族化合物。