1,3-diphenyl-4-bromo-2-buten-1-one | 7462-71-7

• 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: 1,3-diphenyl-4-bromo-2-buten-1-one
• 英文别名: 4-bromo-1,3-diphenyl-2-buten-1-one；γ-bromodypnone；1,3-Diphenyl-4-brom-buten-2-on-(1)；4-Bromo-1,3-diphenylbut-2-en-1-one
• CAS: 7462-71-7
• 化学式: C₁₆H₁₃BrO
• 分子量: 301.183
• InChiKey: GTWVKXCFFOTWRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-diphenyl-4-bromo-2-buten-1-one 在 2-[2,4-bis(4-chlorophenyl)pyrrol-1-yl]phenylamine 作用下， 生成 2,4-diphenylfuran
  参考文献：
  名称：

  An efficient synthesis of 1,3-diaryl-pyrrolo[1,2-a]quinoxalines from 2-(1h-pyrrol-1-yl)phenylamines

  摘要：

  The condensation of 1,3-diaryl-4-bromo-2-buten-1-ones with o-phenylenediamine leads to 2-[2,4-diaryl-1H-pyrrol-1-yl]phenylamines. Heating solutions of these compounds in formic acid leads to formylation and intramolecular condensation to give 1,3-diarylpyrrolo[1,2-a]quinoxalines. The acylation of 2-[2,4-diphenyl-1H-pyrrol-1-yl]phenylamine with acetic anhydride in acetic acid leads to an acetamide, which readily cyclizes to give 4-methyl-1,3-diphenylpyrrolo[1,2-a]quinoxaline upon heating with POCl(3).

  DOI：

  10.1007/s10593-010-0439-8

文献信息

• Applications of Allylsamarium Bromide as a Grignard Reagent and a Single-Electron Transfer Reagent in the One-Pot Synthesis of Dienes and Trienes
  作者：Yuanyuan Hu、Tao Zhao、Songlin Zhang

  DOI：10.1002/chem.200901927

  日期：2010.2.1

  reagent and a single‐electron transfer (SET) reagent in the reaction of α‐halo, γ‐halo‐α,β‐unsaturated ketones and esters with allylsamarium bromide is reported for the first time in this paper. From a synthetic point of view, a general, efficient and experimentally simple one‐pot method for the preparation of 1,4‐dienes and trienes is developed. A possible mechanism of the transformation is proposed.

  首次报道了烯丙基溴化溴作为亲核试剂和单电子转移（SET）试剂在α-卤代，γ-卤代-α，β-不饱和酮和酯与烯丙基溴化reaction的反应中的用途在本文中。从综合的角度出发，开发了一种通用，高效且实验简单的一锅法制备1,4-二烯和三烯的方法。提出了一种可能的转化机制。
• Enantioselective conjugate hydrosilylation of α,β-unsaturated ketones
  作者：Huan Yang、Guanglin Weng、Dongmei Fang、Changjiang Peng、Yuanyuan Zhang、Xiaomei Zhang、Zhouyu Wang

  DOI：10.1039/c9ra01180c

  日期：——

  Enantioselective conjugate hydrosilylation of β,β-disubstituted α,β-unsaturated ketones was realized. In the presence of a chiral picolinamide–sulfonate Lewis base catalyst, the reactions provided various chiral ketones bearing a chiral center at the β-position in up to quantitative yields with moderate enantioselectivities.

  实现了β,β-二取代的α,β-不饱和酮的对映选择性共轭氢化硅烷化。在手性吡啶甲酰胺-磺酸盐路易斯碱催化剂的存在下，反应提供了各种在β位带有手性中心的手性酮，其产率高达定量，具有中等的对映选择性。
• Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives
  作者：L. M. Potikha、V. A. Kovtunenko、A. V. Turov、G. V. Palamarchuk、R. I. Zubatyuk、O. V. Shishkin

  DOI：10.1007/s10593-009-0269-8

  日期：2009.3

  The direction of the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one (γ-bromodypnone) with hydrazines depends on the nature of the substituent they contain. Reaction with 1-methylhydrazinium hydrosulfate gives 1-methyl-3,5-diphenylpyridazin-1-ium bromide but carboxylic acid hydrazides give N-(2,4-diphenyl-1H-pyrrol-1-yl)carboxylic acid amides. γ-Bromodypnone and phenylhydrazine give both 1,3,5-triphenyl-1

  4-溴-1,3-二苯基-2-丁烯-1-酮（γ-溴代嘧啶酮）与肼的反应方向取决于它们所含取代基的性质。与1-甲基肼基硫酸氢盐反应得到1-甲基-3,5-二苯基吡啶并嗪-1-溴化物，而羧酸酰肼得到N-（2,4-二苯基-1H-吡咯-1-基）羧酸酰胺。γ-溴代苯醌和苯肼可同时生成1,3,5-三苯基-1,4-二氢哒嗪和N，2,4-三苯基-1H-吡咯-1-胺（15％）。1-（2,4-二硝基苯基）肼得到（Z）-4-溴-1,3-二苯基-2-丁烯-1-酮的2,4-二硝基苯基hydr。2,4-二苯基-1H-吡咯-1-胺与芳族醛的缩合容易生成N-（芳基亚甲基）-2,4-二苯基-1H-吡咯-1-胺，与甲基碘烷基化得到N，N-二甲基-2,4-二苯基-1H-吡咯-1-胺。
• Synthesis, structure, and properties of 1,3,5-triarylpyridazines
  作者：L. M. Potikha、V. A. Kovtunenko、A. V. Turov

  DOI：10.1007/s10593-009-0354-z

  日期：2009.7

  Treatment of gamma-bromodypnone with arylhydrazines gives differently structured products, i.e. gamma-bromodypnone hydrazones, 1-aryl-3,5-diphenyl-1,4-dihydropyridazines, 1-aryl-3,5-diphenyl-1,6-dihydropyridazines, and aromatic 1,3,5-triarylpyridazinium salts. We have studied the pattern of formation of all of the products and their properties. Heating an alcohol solution of 1,3,5-triphenyl-1,4-dihydropyridazine gives N,2,4-triphenyl-1H-pyrrole-1-amine or to a 1,3,5-triphenylpyridazinium salt dependent upon the acidity of the medium. The product of addition of HBr to the 1,6-dihydropyridazine system is 5-bromo-1-( 4-nitrophenyl)-3,5-diphenyl-1,4,5,6-tetrahydropyridazine.
• Synthesis of 11-methyl-7,9-diphenyl-6H,11H-azepino[2,1-b]-5-benzimidazolium bromide
  作者：V. A. Kovtunenko、L. M. Potikha、A. R. Turelyk、A. V. Turov

  DOI：10.1007/s10593-008-0088-3

  日期：2008.5