trans-(+)-2,3-epoxy-1-(3-thienyl)-3-phenylpropan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-(+)-2,3-epoxy-1-(3-thienyl)-3-phenylpropan-1-one
• 英文别名: [(2S,3R)-3-phenyloxiran-2-yl]-thiophen-3-ylmethanone
• 化学式: C₁₃H₁₀O₂S
• 分子量: 230.287
• InChiKey: ROQYJBKGFQTVNA-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙酰基噻吩 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 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 trans-(+)-2,3-epoxy-1-(3-thienyl)-3-phenylpropan-1-one 、 trans-(+)-2,3-epoxy-1-(3-thienyl)-3-phenylpropan-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

• Julia, Sebastian; Guixer, Joan; Masana, Jaume, Journal of the Chemical Society. Perkin transactions I, 1982, p. 1317 - 1324
  作者：Julia, Sebastian、Guixer, Joan、Masana, Jaume、Rocas, Jose

  DOI：——

  日期：——
• 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.