1-(1-benzyl-2,5-dimethyl-1H-pyrrol-3-yl)-ethanone | 132752-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-benzyl-2,5-dimethyl-1H-pyrrol-3-yl)-ethanone
• 英文别名: Ethanone, 1-[2,5-dimethyl-1-(phenylmethyl)-1H-pyrrol-3-yl]-；1-(1-benzyl-2,5-dimethylpyrrol-3-yl)ethanone
• CAS: 132752-04-6
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: KOHUIOAOLBFZFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-acetylhex-5-yn-2-one 在 吡啶 、 4 A molecular sieve 、 copper dichloride 作用下， 以 甲醇 、 苯 为溶剂， 生成 1-(1-benzyl-2,5-dimethyl-1H-pyrrol-3-yl)-ethanone
  参考文献：
  名称：

  一种合成1,2,3,5-四取代吡咯的新方法

  摘要：

  在与伯胺的反应中，2-炔丙基-1,3-二羰基衍生物，即相应的枯草烯和含二乙氧基磷酰氧基的物质，被转化为相应的1,2,3,5-四取代的吡咯。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:220–225, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20265

  DOI：

  10.1002/hc.20265

文献信息

• Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds
  作者：Ayhan S Demir、Idris M Akhmedov、Özge Sesenoglu

  DOI：10.1016/s0040-4020(02)01298-x

  日期：2002.12

  2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into β-enamino, β-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared

  将2-（2-溴烯丙基）-1,3-二羰基化合物转化为β-烯氨基，β-肼基酸酯和酮，然后进行碱促进的环化反应，从而形成相应的1,2,3,5-四取代吡咯。1,2,4-和1,2,3,4-取代的吡咯也作为次要产物被分离出来。从2-（2-溴烯丙基）-环己烷-1，3-二酮开始，以高收率制备相应的四氢吲哚酮。
• Synthesis of N-substituted pyrrole and tetrahydroindole derivatives from alkenyl β-dicarbonyl compounds
  作者：Helena M.C Ferraz、Fernando L.C Pereira、Fátima S Leite、Marta R.S Nunes、M.Elena Payret-Arrúa

  DOI：10.1016/s0040-4020(99)00625-0

  日期：1999.9

  to the formation of the corresponding pyrrole or tetrahydroindole derivatives. In the absence of base, the iodo-β-enamino esters 5 and 7 underwent spontaneous aromatization after dehydroiodination, furnishing the 4, 5, 6, 7-N-substituted-tetrahydroindoles 19 and 20. All the elimination reactions proceeded smoothly, in yields ranging from 71% to 99%. Starting from the β-allyl-dimedone 21, it was possible

  一系列烯基取代的β-烯氨基酯和酮的碘环化，然后碱促进的脱氢碘化作用，导致形成相应的吡咯或四氢吲哚衍生物。在不存在碱的情况下，碘代-β-烯氨基酯5和7在脱氢碘化后进行自发芳构化，得到4、5、6、7 -N-取代的四氢吲哚19和20。所有消除反应均进行顺利，产率为71％至99％。从β-烯丙基二甲酮21开始，可以以中等的总产率制备氧代四氢吲哚24。
• Gold‐Catalyzed Sequential Amination/Annulation Reactions of 2‐Propynyl‐1,3‐dicarbonyl Compounds
  作者：Antonio Arcadi、Sabrina Di Giuseppe、Fabio Marinelli、Elisabetta Rossi

  DOI：10.1002/1615-4169(200107)343:5<443::aid-adsc443>3.0.co;2-#

  日期：2001.7

  The gold(III)-catalyzed sequential amination/annulation reaction of 2-propynyl-1,3-dicarbonyl compounds 1 with primary amines 2 produces 1,2,3,5-substituted pyrroles 4 in moderate to high yields.
• Silver-catalysed hydroamination: synthesis of functionalised pyrroles
  作者：Ross S. Robinson、Martin C. Dovey、David Gravestock

  DOI：10.1016/j.tetlet.2004.07.019

  日期：2004.8

  It has been shown that functionalised pyrroles can be efficiently prepared using a two-step sequence. This sequence involves the propargylation of secondary enaminones using n-BuLi and propargyl bromide, followed by intramolecular hydroamination catalysed by silver nitrate. The hydroamination can be carried out at room temperature (overnight) or in a domestic microwave oven (60s). (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Functionalized Pyrroles by Reaction of 3,4‐Diacetylhexane‐2,5‐dione with Primary Amines in Water
  作者：Issa Yavari、Maryam Sabbaghan

  DOI：10.1080/00397910701316144

  日期：2007.6.1