(E)-2-[(2-hydroxy-3-nitrocyclohex-2-en-1-yliden)methyl]-thiophene-3-carbaldehyde | 1316054-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-[(2-hydroxy-3-nitrocyclohex-2-en-1-yliden)methyl]-thiophene-3-carbaldehyde
• 英文别名: 2-[(E)-(2-hydroxy-3-nitrocyclohex-2-en-1-ylidene)methyl]thiophene-3-carbaldehyde
• CAS: 1316054-23-5
• 化学式: C₁₂H₁₁NO₄S
• 分子量: 265.29
• InChiKey: MDRHQRRZQODZOL-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-bis(hydroxymethyl)thiophene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 丙酮 为溶剂， 反应 27.5h， 生成 (E)-3-[(2-hydroxy-3-nitrocyclohex-2-en-1-yliden)methyl]-thiophene-2-carbaldehyde 、 (E)-2-[(2-hydroxy-3-nitrocyclohex-2-en-1-yliden)methyl]-thiophene-3-carbaldehyde
  参考文献：
  名称：

  Two chemodivergent anionic domino processes from cyclic α-nitroketones and aromatic aldehydes

  摘要：

  Treatment of cyclic alpha-nitroketones and aromatic 1,2-dialdehydes with DBU in tetrahydrofuran containing small amounts of water proceeded through two chemodivergent one-pot domino pathways, whose outcome depended on the ring size of the starting nitroketone. Thus, alpha-nitrocyclohexanone underwent diastereoselective alpha'-arylmethylenation reactions through a nitroaldol/aldol/reverse nitroaldol mechanism. On the other hand, alpha-nitrocycloheptanone and alpha-nitrocyclooctanone afforded 2-nitroindane-1,2-diols containing three contiguous stereocenters in a highly diastereoselective fashion through a nitroaldol/retro-Dieckmann/intramolecular nitroaldol process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.115

文献信息

• Two chemodivergent anionic domino processes from cyclic α-nitroketones and aromatic aldehydes
  作者：Giorgio Giorgi、Francisco J. Arroyo、Pilar López-Alvarado、J. Carlos Menéndez

  DOI：10.1016/j.tet.2011.05.115

  日期：2011.8

  Treatment of cyclic alpha-nitroketones and aromatic 1,2-dialdehydes with DBU in tetrahydrofuran containing small amounts of water proceeded through two chemodivergent one-pot domino pathways, whose outcome depended on the ring size of the starting nitroketone. Thus, alpha-nitrocyclohexanone underwent diastereoselective alpha'-arylmethylenation reactions through a nitroaldol/aldol/reverse nitroaldol mechanism. On the other hand, alpha-nitrocycloheptanone and alpha-nitrocyclooctanone afforded 2-nitroindane-1,2-diols containing three contiguous stereocenters in a highly diastereoselective fashion through a nitroaldol/retro-Dieckmann/intramolecular nitroaldol process. (C) 2011 Elsevier Ltd. All rights reserved.