1,5-diphenyl-3-(p-tolyl)pentane-1,5-dione | 130317-99-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,5-diphenyl-3-(p-tolyl)pentane-1,5-dione
• 英文别名: 3-(4-Methylphenyl)-1,5-diphenylpentane-1,5-dione
• CAS: 130317-99-6
• 化学式: C₂₄H₂₂O₂
• 分子量: 342.437
• InChiKey: UCOIOTCKMJTUDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-diphenyl-3-(p-tolyl)pentane-1,5-dione 在 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 10.0h， 生成 2,6-diphenyl-4-(p-bromomethylphenyl)pyridine
  参考文献：
  名称：

  Spectral studies of multi-branched fluorescence dyes based on triphenylpyridine core

  摘要：

  A series of novel triphenylpyridine-containing triphenylamine derivatives have been carefully designed and prepared in good yields using the stepwise route reactions. The relationship of photoluminescence property and structure of compounds 9-13 was systematically investigated via UV-vis, fluorescence, thermogravimetric and electrochemical analyzer. The highest occupied molecular orbital and the lowest unoccupied molecular orbital distributions of compounds 9-13 were calculated by density functional theory method. The high fluorescence quantum yields, desirable the highest occupied molecular orbital levels and high thermal stability of compounds 9-13 indicate that the linkage of triphenylpyridine and triphenylamine is an efficient means to enhance hole-transporting ability and fluorescent quantum yield. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.10.087
• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 在 copper(l) iodide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以72%的产率得到1,5-diphenyl-3-(p-tolyl)pentane-1,5-dione
  参考文献：
  名称：

  Copper-catalyzed synthesis of 1,3,5-triarylpentane-1,5-diones from α,β-unsaturated ketones

  摘要：

  使用α，β-不饱和酮作为独特的起始物质，描述了一种高效的铜催化合成1,3,5-三芳基戊二酮的方法。

  DOI：

  10.1039/c5ra09155a

文献信息

• N-Heterocyclic Carbene-Catalysed Mukaiyama–Michael Reaction and Mukaiyama Aldol/Mukaiyama–Michael Three-Component Coupling Reaction
  作者：Kim Nguyen、David W. Lupton

  DOI：10.1071/ch16566

  日期：——

  ethers and chalcone derivatives has been discovered. In addition, a related reaction cascade involving dehydrative Mukaiyama aldol followed by a Mukaiyama–Michael addition process has been developed. The later reaction can also be achieved as a three-component coupling reaction. The enantioselective variant of these reactions has been examined with homochiral catalysts. Though these catalysts were active

  一个Ñ -杂环卡宾催化的几个三甲基甲硅烷（TMS）的烯醇醚和查耳酮衍生物之间向山-迈克尔加成已经发现。另外，已经开发出了一种涉及脱水穆凯山山醇醛的随后的反应级联，随后是穆凯山山-迈克尔的加成过程。后面的反应也可以作为三组分偶联反应来实现。这些反应的对映选择性变体已经用同手性催化剂检查过。尽管这些催化剂是活性的，但它们未能实现对映体诱导。
• Unexpected synthesis of 1,3,5-triarly-1,5-diketones from aryl ketones via di-enamine mechanism
  作者：Bin Liu、Junfeng Wang、Yi Pang、Zemei Ge、Runtao Li

  DOI：10.1016/j.tet.2014.10.009

  日期：2014.12

  An unexpected reaction of aryl ketone with acetohydrazone of aromatic aldehyde via 1,2-di-enamine/di-iminium mechanism was discovered, leading to efficient synthesis of 1,3,5-triaryl-1,5-diketones in good to excellent yields.

  发现芳基酮与芳香醛的乙酰nium通过1,2-二烯胺/二亚胺机理的意外反应，导致1,3,5-三芳基-1,5-二酮的高效合成，收率良好。
• A Novel Formation of Phenyl-Substituted Pyridines by the Reaction of<i>N</i>-(Diphenylphosphinyl)-1-azaallyl Anions with α,β-Unsaturated Carbonyl Compounds. A New Synthetic Equivalent of Primary Vinylamines
  作者：Tomoshige Kobayashi、Hiroshi Kawate、Hidetaka Kakiuchi、Hiroshi Kato

  DOI：10.1246/bcsj.63.1937

  日期：1990.7

  1-propanone and 1,5-pentanedione derivatives. A plausible mechanism involving a sequence of Michael addition and intramolecular aza-Horner-Wittig reaction is described, and the 1-azaallyl anions were found to behave as a synthetic equivalent of primary vinylamines.

  N-膦酰基-1-氮杂烯丙基阴离子衍生自相应的亚胺或烯胺，与α,β-不饱和羰基化合物反应生成苯基取代的吡啶以及1-丙酮和1,5-戊二酮衍生物。描述了涉及一系列迈克尔加成和分子内氮杂-霍纳-维蒂希反应的合理机制，并且发现 1-氮杂烯丙基阴离子的行为与伯乙烯胺的合成等效物相同。
• A direct green route towards the synthesis of 2-aroyl-3,5-diarylthiophenes from 1,5-diketones
  作者：Rengasamy Chithiravel、Kandasamy Rajaguru、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c5ra17829k

  日期：——

  The synthesis of 2-aroyl-3,5-diarylthiophenes has been achieved from various 1,5-diketones with elemental sulphur and morpholine under microwave irradiation following a greener protocol.

  已经通过微波辐射在一种更环保的方法下，利用各种1,5-二酮与元素硫和吗啡啶合成了2-芳酰基-3,5-二芳基噻吩。
• Carbon–Carbon Bond Cleavage Reaction: Synthesis of Multisubstituted Pyrazolo[1,5-<i>a</i>]pyrimidines
  作者：Pallabi Saikia、Sanjib Gogoi、Romesh C Boruah

  DOI：10.1021/acs.joc.5b00933

  日期：2015.7.2

  A new carbon–carbon bond cleavage reaction was developed for the efficient synthesis of multisubstituted pyrazolo[1,5-a]pyrimidines. This base induced reaction of 1,3,5-trisubstituted pentane-1,5-diones and substituted pyrazoles afforded good yields of the pyrazolo[1,5-a]pyrimidines.

  为了有效合成多取代的吡唑并[1,5- a ]嘧啶，开发了一种新的碳-碳键裂解反应。该碱诱导的1,3,5-三取代戊烷-1,5-二酮与取代的吡唑的反应提供了吡唑并[1,5- a ]嘧啶的良好收率。