2-Bis-<2-hydroxyethyl>-aminomethyl-thiophen | 7006-62-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Bis-<2-hydroxyethyl>-aminomethyl-thiophen
• 英文别名: 2-Di-<2-hydroxy-ethyl>-aminomethyl-thiophen；2--thiophen；bis-(2-hydroxy-ethyl)-[2]thienylmethyl-amine；Bis-(2-hydroxy-aethyl)-[2]thienylmethyl-amin；2-[2-Hydroxyethyl(thiophen-2-ylmethyl)amino]ethanol
• CAS: 7006-62-4
• 化学式: C₉H₁₅NO₂S
• mdl: MFCD16151953
• 分子量: 201.29
• InChiKey: LJOYLVVARBBLHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Bis-<2-hydroxyethyl>-aminomethyl-thiophen 在 rubidium carbonate 、 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 9-nitro-2-(2,4,6-triisopropylphenyl)-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 24.0h， 生成 (E)-2-((3-(4-fluorophenyl)acryloyl)oxy)-N-(2-hydroxyethyl)-N-(thiophen-2-ylmethyl)ethan-1-amine oxide
  参考文献：
  名称：

  10.1002/anie.202404979

  摘要：

  AbstractThe control of noncarbon stereogenic centers is of profound importance owing to their enormous interest in bioactive compounds and chiral catalyst or ligand design for enantioselective synthesis. Despite various elegant approaches have been achieved for construction of S‐, P‐, Si‐ and B‐stereocenters over the past decades, the catalyst‐controlled strategies to govern the formation of N‐stereogenic compounds have garnered less attention. Here, we disclose the first organocatalytic approach for efficient access to a wide range of nitrogen‐stereogenic compounds through a desymmetrization approach. Intriguingly, the pro‐chiral remote diols, which are previously not well addressed with enantiocontrol, are well differentiated by potent chiral carbene‐bound acyl azolium intermediates. Preliminary studies shed insights on the critical importance of the ionic hydrogen bond (IHB) formed between the dimer aggregate of diols to afford the chiral N‐oxide products that feature a tetrahedral nitrogen as the sole stereogenic element with good yields and excellent enantioselectivities. Notably, the chiral N‐oxide products could offer an attractive strategy for chiral ligand design and discovery of potential antibacterial agrochemicals.

  DOI：

  10.1002/anie.202404979
• 作为产物：
  描述：

  2-氯甲基噻吩 、 二乙醇胺 生成 2-Bis-<2-hydroxyethyl>-aminomethyl-thiophen
  参考文献：
  名称：

  Nitrogen Mustards

  摘要：

  DOI：

  10.1021/ja01152a023

文献信息

• Nitrogen Mustards
  作者：Evelyn Wilson、Max Tishler

  DOI：10.1021/ja01152a023

  日期：1951.8
• 10.1002/anie.202404979
  作者：Luo, Zhongfu、Liao, Minghong、Li, Wei、Zhao, Sha、Tang, Kun、Zheng, Pengcheng、Chi, Yonggui Robin、Zhang, Xinglong、Wu, Xingxing

  DOI：10.1002/anie.202404979

  日期：——

  AbstractThe control of noncarbon stereogenic centers is of profound importance owing to their enormous interest in bioactive compounds and chiral catalyst or ligand design for enantioselective synthesis. Despite various elegant approaches have been achieved for construction of S‐, P‐, Si‐ and B‐stereocenters over the past decades, the catalyst‐controlled strategies to govern the formation of N‐stereogenic compounds have garnered less attention. Here, we disclose the first organocatalytic approach for efficient access to a wide range of nitrogen‐stereogenic compounds through a desymmetrization approach. Intriguingly, the pro‐chiral remote diols, which are previously not well addressed with enantiocontrol, are well differentiated by potent chiral carbene‐bound acyl azolium intermediates. Preliminary studies shed insights on the critical importance of the ionic hydrogen bond (IHB) formed between the dimer aggregate of diols to afford the chiral N‐oxide products that feature a tetrahedral nitrogen as the sole stereogenic element with good yields and excellent enantioselectivities. Notably, the chiral N‐oxide products could offer an attractive strategy for chiral ligand design and discovery of potential antibacterial agrochemicals.