2,4-dibenzoyl-1,5-di-p-tolylpentane-1,5-dione | 1340475-93-5

• 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: 2,4-dibenzoyl-1,5-di-p-tolylpentane-1,5-dione
• 英文别名: 2,4-Dibenzoyl-1,5-bis(4-methylphenyl)pentane-1,5-dione；2,4-dibenzoyl-1,5-bis(4-methylphenyl)pentane-1,5-dione
• CAS: 1340475-93-5
• 化学式: C₃₃H₂₈O₄
• 分子量: 488.583
• InChiKey: NSSFVCDLCIZKGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-甲基苯基)-3-苯基-1,3-丙烷二酮 在 gold(III) chloride 、 硝基甲烷 作用下， 反应 4.0h， 以93%的产率得到2,4-dibenzoyl-1,5-di-p-tolylpentane-1,5-dione
  参考文献：
  名称：

  Gold/copper-catalyzed activation of the aci-form of nitromethane in the synthesis of methylene-bridged bis-1,3-dicarbonyl compounds

  摘要：

  使用Lewis酸激活硝基甲烷的酸形式，以进行碳亲核试剂的攻击的研究已经开展。在催化量的AuCl₃或Cu(OTf)₂存在的条件下，硝基甲烷溶剂中的1,3-二羰基化合物可以转化为亚甲基桥联的双1,3-二羰基化合物。

  DOI：

  10.1039/c1cc14926a

文献信息

• Aerobic Oxidation of a Tertiary Aliphatic Amine Under Visible-Light Photocatalysis: Facile Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds
  作者：Woo-Jin Yoo、Arata Tanoue、Shū Kobayashi

  DOI：10.1002/asia.201200807

  日期：2012.12

  Lights, camera, action! An efficient protocol for the formation of methylene‐bridged bis‐1,3‐dicarbonyl compounds has been developed through an aerobic photocatalytic oxidative coupling reaction between 1,3‐dicarbonyl compounds and a tertiary aliphatic amine.

  灯光，摄像头，动作！通过1,3-二羰基化合物与脂族叔胺之间的需氧光催化氧化偶联反应，已开发出形成亚甲基双bis-1,3-二羰基化合物的有效方法。
• Acid-promoted oxidative methylenation of 1,3-dicarbonyl compounds with DMSO: application to the three-component synthesis of Hantzsch-type pyridines
  作者：LuLu Xue、Guolin Cheng、Ruifeng Zhu、Xiuling Cui

  DOI：10.1039/c7ra07442e

  日期：——

  A highly convergent one-pot synthesis of Hantzsch-type pyridines has been developed based on a three-component annulation of 1,3-dicarbonyl compounds, DMSO, and ammonium salt. A transition-metal-free oxidative methylenation reaction/Hantzsch pyridine synthesis cascade reaction was involved in this process. This intermolecular annulation reaction proceeds under mild reaction conditions, wherein DMSO

  基于1,3-二羰基化合物，DMSO和铵盐的三组分环化反应，已开发出高度收敛的一锅法合成Hantzsch型吡啶。该过程涉及无过渡金属的氧化亚甲基化反应/汉茨吡啶合成级联反应。该分子间环化反应在温和的反应条件下进行，其中DMSO用作溶剂，碳源和氧化剂。以高收率制备了一系列多取代的吡啶和亚甲基桥联的双-1,3-二羰基化合物。
• Facile synthesis of bis-1,3-dicarbonyl compounds using inert dichloromethane as a one-carbon source
  作者：Li-Ming Jiang、Kai Xiang、Hai-Juan Jiao、Jing-Lin Yang、Heng-Tong Qu、Xue-Tao Xu、Wen-Bao、Dao-Yong Zhu、Shao-Hua Wang

  DOI：10.1016/j.tetlet.2023.154564

  日期：2023.6

  simple and convenient procedure for the preparation of valuable bis-1,3-dicarbonyl-substituted methane compounds and their derivatives has been developed using inert dichloromethane as one-carbon source in good to excellent yields. The advantages of this protocol are mild reaction conditions, easily scalable and good functional group compatibility. Moreover, the use of cyclic secondary amine as the promoter

  使用惰性二氯甲烷作为单碳源，开发了一种制备有价值的双-1,3-二羰基取代的甲烷化合物及其衍生物的简单方便的方法，收率良好。该协议的优点是反应条件温和、易于扩展和良好的功能组兼容性。此外，使用环状仲胺作为促进剂避免了过渡金属催化剂和氧化剂的存在。
• Visible-light photoredox-mediated oxidation of N-methyl tertiaryamines under catalyst free conditions: Direct synthesis of methylene-bridged bis-1,3-dicarbonyl compounds
  作者：Xiao-Jun Dai、Xiao-Liang Xu、Dong-Ping Cheng、Xiao-Nian Li

  DOI：10.1016/j.cclet.2014.01.021

  日期：2014.4

  Mediated by visible light-induced photoredox catalysis and free of other catalysts, a new and efficient synthesis of methylene-bridged bis-1,3-dicarbonyl derivatives has been developed. A variety of N-methyl tertiaryamines and 1,3-dicarbonyl compounds were investigated in this reaction. (C) 2014 Xiao-Liang Xu and Xiao-Nian Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Oxidative C(Sp3)–H activation and C–N cleavage of N-methyl amines under transition-metal-free condition for synthesis of methylene-bridged bis-1,3-diketones
  作者：Xiaohu Wang、Yi Wang、Yu Yuan、Chun-Hui Xing

  DOI：10.1016/j.tet.2014.01.033

  日期：2014.3

  A transition-metal-free oxidative methylenation reaction was developed. Methylene-bridged bis-1,3-dicarbonyl compounds were synthesized by oxidative C(Sp(3))-H activation and C-N cleavage of N-methyl amines. This novel reaction avoids the use of transition metal catalyst. Furthermore, the reaction are very mild and operational convenient. (C) 2014 Elsevier Ltd. All rights reserved.