2-Phenyl-2,5-dihydrothiophene-3-carbaldehyde | 1417794-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Phenyl-2,5-dihydrothiophene-3-carbaldehyde
• 英文别名: 2-phenyl-2,5-dihydrothiophene-3-carbaldehyde
• CAS: 1417794-97-8
• 化学式: C₁₁H₁₀OS
• 分子量: 190.266
• InChiKey: LZRDLFFYSDKMGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴代硝基甲烷 、 2-Phenyl-2,5-dihydrothiophene-3-carbaldehyde 在 DL-脯氨酸 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 16.17h， 以68%的产率得到6-nitro-2-phenyl-3-thiabicyclo[3.1.0]hexane-1-carbaldehyde
  参考文献：
  名称：

  Diastereoselective nitrocyclopropanation of 2,5-dihydrothiophene-3-carbaldehydes

  摘要：

  An unprecedented domino Michael/alpha-alkylation reaction between 2,5-dihydrothiophene-3-carbaldehydes and bromonitromethane is presented. This process, efficiently catalyzed by DL-proline in the presence of MeOH/NaOAc system, provides access to novel 6-nitro-3-thiabicyclo[3.1.0]hexane-1-carbaldehyde derivatives in good yields with good to excellent diastereoselectivities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.134
• 作为产物：
  描述：

  1,4-二硫-2,5-二醇 、 肉桂醛 在 四氢吡咯 、 苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.17h， 以75%的产率得到2-Phenyl-2,5-dihydrothiophene-3-carbaldehyde
  参考文献：
  名称：

  Diastereoselective nitrocyclopropanation of 2,5-dihydrothiophene-3-carbaldehydes

  摘要：

  An unprecedented domino Michael/alpha-alkylation reaction between 2,5-dihydrothiophene-3-carbaldehydes and bromonitromethane is presented. This process, efficiently catalyzed by DL-proline in the presence of MeOH/NaOAc system, provides access to novel 6-nitro-3-thiabicyclo[3.1.0]hexane-1-carbaldehyde derivatives in good yields with good to excellent diastereoselectivities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.134

文献信息

• Diastereoselective nitrocyclopropanation of 2,5-dihydrothiophene-3-carbaldehydes
  作者：Carmela De Risi、Simonetta Benetti、Marco Fogagnolo、Valerio Bertolasi

  DOI：10.1016/j.tetlet.2012.10.134

  日期：2013.1

  An unprecedented domino Michael/alpha-alkylation reaction between 2,5-dihydrothiophene-3-carbaldehydes and bromonitromethane is presented. This process, efficiently catalyzed by DL-proline in the presence of MeOH/NaOAc system, provides access to novel 6-nitro-3-thiabicyclo[3.1.0]hexane-1-carbaldehyde derivatives in good yields with good to excellent diastereoselectivities. (C) 2012 Elsevier Ltd. All rights reserved.