(2R)-2-deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene | 94885-54-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R)-2-deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene
• CAS: 94885-54-8
• 化学式: C₉H₉NO₂S
• 分子量: 196.234
• InChiKey: DCCSWNQBUXUGBQ-DUVJLBCISA-N

反应信息

• 作为反应物：
  描述：

  (2R)-2-deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 43.0h， 以24%的产率得到(1S,2R)-2-deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene-1-oxide
  参考文献：
  名称：

  Magnetic resonance study of diastereomeric interactions of nitroaromatic sulfxides with alcohols in solution

  摘要：

  AbstractThe synthesis of optically active (1R,2R)‐ and (1S,2R)‐2‐deuterio‐2,3‐dihydro‐2‐methyl‐6‐nitrobenzothiophene‐1‐oxide (3 and 4) is described. Several racemic aryl methyl carbinols in the presence of 3 or 4 give different chemical shifts for enantiomeric CH, CH3 and OH protons. These chemical shift differences are larger than those observed in analogous sulfoxide–alcohol pairs without nitro groups. Quinine and cinchonidine cause observable non‐equivalence of methylene and aromatic protons in racemic 4. The magnitude of the diastereomeric shift difference is sensitive to temperature, solvent, concentration, nature of the π system and steric effects.

  DOI：

  10.1002/mrc.1270220902
• 作为产物：
  描述：

  (2R)-2-deuterio-2,3-dihydro-2,S-dimethyl-6-nitrobenzothiophene perchlorate 在 potassium bromide 作用下， 反应 0.33h， 以100%的产率得到(2R)-2-deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene
  参考文献：
  名称：

  Magnetic resonance study of diastereomeric interactions of nitroaromatic sulfxides with alcohols in solution

  摘要：

  AbstractThe synthesis of optically active (1R,2R)‐ and (1S,2R)‐2‐deuterio‐2,3‐dihydro‐2‐methyl‐6‐nitrobenzothiophene‐1‐oxide (3 and 4) is described. Several racemic aryl methyl carbinols in the presence of 3 or 4 give different chemical shifts for enantiomeric CH, CH3 and OH protons. These chemical shift differences are larger than those observed in analogous sulfoxide–alcohol pairs without nitro groups. Quinine and cinchonidine cause observable non‐equivalence of methylene and aromatic protons in racemic 4. The magnitude of the diastereomeric shift difference is sensitive to temperature, solvent, concentration, nature of the π system and steric effects.

  DOI：

  10.1002/mrc.1270220902