(2R,3S)-2,3-epoxy-1-(2-pyrrolyl)-3-(1-naphthyl)-propan-1-one | 1285718-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S)-2,3-epoxy-1-(2-pyrrolyl)-3-(1-naphthyl)-propan-1-one
• 英文别名: [(2R,3S)-3-naphthalen-1-yloxiran-2-yl]-(1H-pyrrol-2-yl)methanone
• CAS: 1285718-98-0
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: CPLXKVMLABUPIN-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基吡咯 在 Methyl-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosido[2,3-h]-N-3-hydroxypropyl-1,4,7,10-tetraoxa-13-azacyclopentadecane 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 0.8h， 生成 (2S,3R)-2,3-epoxy-1-(2-pyrrolyl)-3-(1-naphthyl)-propan-1-one 、 (2R,3S)-2,3-epoxy-1-(2-pyrrolyl)-3-(1-naphthyl)-propan-1-one
  参考文献：
  名称：

  Enantioselective synthesis of heteroaromatic epoxyketones under phase-transfer catalysis using d-glucose- and d-mannose-based crown ethers

  摘要：

  Heteroaromatic epoxyketones have been synthesized in an asymmetric Darzens condensation of 2-chloroacetylfuran or 2- and 3-chloroacetylthiophene with aromatic aldehydes and in the enantioselective epoxidation of alpha,beta-enones with an N-methylpyrrole unit, in both cases in the presence of D-glucose- 1 or D-mannose-based 2 crown ethers as phase transfer catalysts. The use of D-glucose-based 1 lariat ether as the catalyst gave the best results. The alpha,beta-epoxyketones with a furan or a thiophene moiety were obtained in good enantioselectivities (up to 86% ee) as well as excellent diastereoselectivities (up to 98:2), but the epoxyketones with a pyrrole-ring were formed in the Darzens condensation in low yields and enantioselectivities. The epoxyketones with an N-methylpyrrole moiety isolated from the epoxidation of the corresponding alpha,beta-enones were obtained in significant enantioselectivities (in ee values up to 81%) in the presence of catalyst 1 under mild reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.001

文献信息

• Asymmetric C–C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers
  作者：Péter Bakó、Zsolt Rapi、György Keglevich、Tamás Szabó、Péter L. Sóti、Tamás Vígh、Alajos Grűn、Tamás Holczbauer

  DOI：10.1016/j.tetlet.2011.01.094

  日期：2011.3

  phase asymmetric Darzens condensations were promoted by d-glucose- and d-mannose-based crown ethers. The corresponding aromatic and heteroaromatic α,β-epoxyketones were obtained with moderate to high enantioselectivities (up to 96%) as well as diastereoselectivities (up to 98:2) under mild reaction conditions. The absolute configurations of several of the epoxyketones were determined by single crystal

  d-葡萄糖和d-甘露糖基冠醚促进了液相-液相不对称Darzens缩合反应。在温和的反应条件下，获得了具有中等至高对映选择性（最高96％）以及非对映选择性（最高98：2）的相应芳族和杂芳族α，β-环氧酮。通过单晶X射线分析确定几种环氧酮的绝对构型。乙酰氨基丙二酸二乙酯在反式-β-硝基烯烃中的迈克尔加成反应是在固-液两相系统中，在以d-葡萄糖为基础的冠状催化剂存在下，ee高达99％。
• Enantioselective synthesis of heteroaromatic epoxyketones under phase-transfer catalysis using d-glucose- and d-mannose-based crown ethers
  作者：Zsolt Rapi、Tamás Szabó、György Keglevich、Áron Szöllősy、László Drahos、Péter Bakó

  DOI：10.1016/j.tetasy.2011.07.001

  日期：2011.6

  Heteroaromatic epoxyketones have been synthesized in an asymmetric Darzens condensation of 2-chloroacetylfuran or 2- and 3-chloroacetylthiophene with aromatic aldehydes and in the enantioselective epoxidation of alpha,beta-enones with an N-methylpyrrole unit, in both cases in the presence of D-glucose- 1 or D-mannose-based 2 crown ethers as phase transfer catalysts. The use of D-glucose-based 1 lariat ether as the catalyst gave the best results. The alpha,beta-epoxyketones with a furan or a thiophene moiety were obtained in good enantioselectivities (up to 86% ee) as well as excellent diastereoselectivities (up to 98:2), but the epoxyketones with a pyrrole-ring were formed in the Darzens condensation in low yields and enantioselectivities. The epoxyketones with an N-methylpyrrole moiety isolated from the epoxidation of the corresponding alpha,beta-enones were obtained in significant enantioselectivities (in ee values up to 81%) in the presence of catalyst 1 under mild reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.