1,5-diphenyl-3-(2-pyridiyl)pentane-1,5-dione | 5337-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-diphenyl-3-(2-pyridiyl)pentane-1,5-dione
• 英文别名: 1,5-diphenyl-3-(pyridin-2-yl)pentane-1,5-dione；1,5-diphenyl-3-(pyridine-2-yl)pentane-1,5-dione；1,5-diphenyl-3-(2-pyridyl)pentane-1,5-dione；1,5-Diphenyl-3-[2]pyridyl-pentan-1,5-dion；1,5-diphenyl-3-pyridin-2-ylpentane-1,5-dione
• CAS: 5337-48-4
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: ZQXGBLSJLHFSOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-diphenyl-3-(2-pyridiyl)pentane-1,5-dione 以46%的产率得到
  参考文献：
  名称：

  POHJALA E. K., ACTA CHEM. SCAND. , 1976, B 30, NO 6, 512-516

  摘要：

  DOI：
• 作为产物：
  描述：

  吡啶-2-甲醛 、 苯乙酮 在 NaOH/Al₂O₃ 作用下， 反应 0.12h， 以80%的产率得到1,5-diphenyl-3-(2-pyridiyl)pentane-1,5-dione
  参考文献：
  名称：

  NaOH-Al2O3 Catalyzed Synthesis of 1, 3, 5-triarylpentane-1, 5-diones Derivatives Under Solvent-Free Condition and Crystal Structure of 3-(2', 4'-dichlorophenyl)-1, 5-diphenylpentane-1, 5-dione

  摘要：

  以芳香醛和芳香酮为起始原料，在 NaOH/Al2O3 和无溶剂条件下通过串联醛醇反应/迈克尔加成法快速合成 1,3,5-三芳基戊烷-1,5-二酮化合物的高效程序已经得到描述。所有化合物都通过红外光谱、1H NMR 和元素分析进行了表征。此外，还获得了 3-(2',4'-二氯苯基)-1,5-二苯基戊烷-1,5-二酮的晶体结构，并通过 X 射线单晶衍射测定了其晶体结构。该方案具有程序简单、环保、反应条件温和等优点。

  DOI：

  10.2174/157017812800233732

文献信息

• Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN
  作者：Muthupandi Nagaraj、Muthusamy Boominathan、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c1ob05232b

  日期：——

  simple and efficient protocol for the construction of substituted piperazines, piperidines, thiomorpholines, decahydroquinolines, perhydrocyclopenta[b]pyridine, and pyrrolidines bearing N-hydroxy substituents through intramolecular reductive cyclization of diketoximes using sodium cyanoborohydride is described.

  描述了使用氰基硼氢化钠通过二酮肟的分子内还原环化反应来构建带有N-羟基取代基的取代哌嗪，哌啶，硫吗啉，十氢喹啉，全氢环戊[b]吡啶和吡咯烷的简单有效的方法。
• Synthesis, structural, electrochemical, and photophysical properties of 4,2′-thiopyrylogens - a novel class of sensitizers for photoinduced electron transfer reactions
  作者：Ajaya Kumar Sankara Warrier、Edward L. Clennan

  DOI：10.1002/poc.1697

  日期：2011.1

  The first three examples of the thioanalog of the 4,2′‐pyrylogen ring system are reported. The influence of the sulfur atom on the structural, electrochemical, and photophysical behavior of this ring system is discussed. In addition, these 4,2′‐thiopyrylogens are compared to their previously reported 4,4′‐isomers and their 4,4′‐ and 4,2′‐oxygen analogs. Copyright © 2010 John Wiley & Sons, Ltd.

  报道了4，2′-吡咯烷酮环系统的硫代类似物的前三个例子。讨论了硫原子对该环体系的结构，电化学和光物理行为的影响。此外，将这些4,2'-硫代吡喃缩醛与先前报道的4,4'-异构体以及4,4'-和4,2'-氧类似物进行了比较。版权所有©2010 John Wiley＆Sons，Ltd.
• Profft et al., Journal fur praktische Chemie (Leipzig 1954), 1955, vol. <4>2, p. 147,159
  作者：Profft et al.

  DOI：——

  日期：——
• PYRIDINE ANALOGS OF CHALCONE AND THEIR POLYMERIZATION REACTIONS
  作者：C. S. MARVEL、LESTER E. COLEMAN、GEORGE P. SCOTT

  DOI：10.1021/jo01364a031

  日期：1955.12
• N- vs O-Coordination in cyclomanganation of 1,5-diaryl-3-(2-pyridyl)pentane-1,5-diones and 3-(2-pyridyl)chalcones; cyclomanganation at saturated carbon and the crystal structure of [1,5-diphenyl-κC2-3-(2-pyridyl- κN)pentan-2-yl-κC2-1,5-dione-κO1κO5]tetracarbonylmanganesetricarbonylmanganese
  作者：Warren Tully、Lyndsay Main、Brian K. Nicholson

  DOI：10.1016/j.jorganchem.2005.04.016

  日期：2005.7

  Reaction of 1,5-diphenyl-3-(2-pyridyl)pentane-1,5-dione (5a) with 2.5 moles of benzylpentacarbonylmanganese in petroleum spirit under reflux gives a small amount of the symmetric di-aryl-manganated product [1,5-diphenyl-kappa C-2-3-(2-pyridyl)pentane-1,5-dione-kappa O(1)kappa O-5]bis-(tetracarbonylmanganese) (7a), but mostly [1,5-diphenyl-kappa C-2-3-(2-pyridyl-kappa N)pentan-2-yl-kappa C-2-1,5-dione-kappa O(1)kappa O-5]tetracarbonylmanganesetricarbonylmanganese (6a) which is manganated at only one aryl carbon [by Mn(CO)4] but also [by Mn(CO)3 with N and O coordination] at the methylene carbon adjacent to the Mn(CO)(4)-coordinated ketone carbonyl. The latter is a rare example of direct cyclomanganation at a saturated carbon and the only known case adjacent to a carbonyl group; the X-ray crystal structure of 6a is reported. With 3 moles of benzylpentacarbonylmanganese the yield of 6a remains unchanged but some trimanganation product [1, 5-diphenyl-kappa C(2')kappa C-2'''-3-(2-pyridyl-kappa N)pentan-2-yl-kappa C-2-1,5-dione-kappa O(1)kappa O-5]tris-(tetracarbonylmanganese) (8a) is formed, presumably from 7a. Routes to products are proposed and activating factors considered. 1,5-Di-(2-thienyl)-3-(2-pyridyl)pentane-1,5-dione (5b) and its 3-thienyl isomer (5c) similarly give 6a analogues [1,5-di-(2-thienyl-kappa C-3)-3-(2-pyridyl-kappa N)pentan-2-yl-kappa C-2-1, 5-dione-kappa O(1)kappa O-5]tetracarbonylmanganesetricarbonylmanganese (6b) and [1,5-di-(3-thienyl-kappa C-2)-3-(2-pyridyl-kappa N)pentan-2-yl-kappa C-2-1,5-dione-kappa O(1)kappa O-5]tetracarbonylmanganesetricarbonylmanganese (6c).Also reported are the mono-cyclomanganation product [1-(2,6-dimethoxyphenyl)-3-(2-pyridyl-kappa N)prop-2-en-2-yl-kappa C-1-one]tetracarbonylmanganese (16) and dicyclomanganation product [1-(2,5-dimethyl-3-thienyl-kappa C-4)-3-(2-pyridyl-kappa N)prop-2-en-2-yl-kappa C-2-1-one-kappa O]bis-(tetracarbonylmanganese) (17) from reaction of the respective (E)-1-aryl-3-(2-pyridyl)prop-2-en-1-ones(3-(2-pyridyl)chalcones), the first reported examples of enone metallation at the alpha-carbon via N-coordination by a beta-2-pyridyl group. (c) 2005 Elsevier B.V. All rights reserved.