(R)-(+)-1-[2,5-dimethyl-1-(1-phenyl-ethyl)-1H-pyrrol-3-yl]ethanone | 369657-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-1-[2,5-dimethyl-1-(1-phenyl-ethyl)-1H-pyrrol-3-yl]ethanone
• 英文别名: Ethanone, 1-[2,5-dimethyl-1-[(1R)-1-phenylethyl]-1H-pyrrol-3-yl]-；1-[2,5-dimethyl-1-[(1R)-1-phenylethyl]pyrrol-3-yl]ethanone
• CAS: 369657-07-8
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: TVFZWKHIVNLBRD-GFCCVEGCSA-N

物化性质

• 沸点：
  367.0±37.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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 、 R(+)-alpha-甲基苄胺 在 sodium tetrachloroaurate(III) 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (R)-(+)-1-[2,5-dimethyl-1-(1-phenyl-ethyl)-1H-pyrrol-3-yl]ethanone
  参考文献：
  名称：

  Gold‐Catalyzed Sequential Amination/Annulation Reactions of 2‐Propynyl‐1,3‐dicarbonyl Compounds

  摘要：

  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.

  DOI：

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

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。
• 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.
• Conversion of homochiral amines and α-amino esters to their chiral 1,2,3,5-substituted pyrrole derivatives via gold-catalysed amination/annulation reactions of 2-propynyl-1,3-dicarbonyl compounds
  作者：Antonio Arcadi、Sabrina Di Giuseppe、Fabio Marinelli、Elisabetta Rossi

  DOI：10.1016/s0957-4166(01)00468-2

  日期：2001.10

  Homochiral primary amines, amino alcohols and alpha -amino esters have been reacted with 2-propynyl-1,3-dicarbonyl compounds under gold catalysis leading to 1,2,5-trisubstituted 3-acylpyrrole derivatives in moderate to high yields and high enantiomeric excess. (C) 2001 Elsevier Science Ltd. All rights reserved.