N-(((1R,2S,5S)-2-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)-N,4-dimethylbenzenesulfonamide | 1187848-53-8

• 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: N-(((1R,2S,5S)-2-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)-N,4-dimethylbenzenesulfonamide
• 英文别名: N-[[(1R,2S,5S)-2-hydroxy-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]methyl]-N,4-dimethylbenzenesulfonamide
• CAS: 1187848-53-8
• 化学式: C₁₈H₂₇NO₃S
• 分子量: 337.483
• InChiKey: YQENJAHCDQNVEC-YXJHDRRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(((1R,2S,5S)-2-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)-N,4-dimethylbenzenesulfonamide 在 氨 、 sodium 、 水 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 5.0h， 以37%的产率得到(1R,2S,5S)-6,6-dimethyl-2-((methylamino)methyl)bicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of new monoterpene β-amino alcohols

  摘要：

  The regio- and stereoselective osmium-catalysed aminohydroxylation of (+)-2-carene (99% ee), and (+)-3-carene (99% ee), (-)-beta-pinene (99% ee) and (-)-camphene (75% ee) with chloramine-T is described. The products beta-hydroxy-beta-toluenesulfonamides were reduced with sodium in liquid ammonia to give the corresponding beta-amino alcohols with 48-83% yields. The methylation-reduction of beta-hydroxy-beta-toluene-sulfonamides gave beta-methylamino alcohols with 33-55% yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.06.007
• 作为产物：
  描述：

  N-(((1R,2S,5S)-2-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)-4-methylbenzenesulfonamide 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以99%的产率得到N-(((1R,2S,5S)-2-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Stereoselective synthesis of new monoterpene β-amino alcohols

  摘要：

  The regio- and stereoselective osmium-catalysed aminohydroxylation of (+)-2-carene (99% ee), and (+)-3-carene (99% ee), (-)-beta-pinene (99% ee) and (-)-camphene (75% ee) with chloramine-T is described. The products beta-hydroxy-beta-toluenesulfonamides were reduced with sodium in liquid ammonia to give the corresponding beta-amino alcohols with 48-83% yields. The methylation-reduction of beta-hydroxy-beta-toluene-sulfonamides gave beta-methylamino alcohols with 33-55% yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.06.007