N-But-3-enyl-N-[(1S,4S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohept-2-enyl]-2-nitro-benzenesulfonamide | 482376-67-0

• 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-But-3-enyl-N-[(1S,4S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohept-2-enyl]-2-nitro-benzenesulfonamide
• CAS: 482376-67-0
• 化学式: C₂₃H₃₆N₂O₆SSi
• 分子量: 496.7
• InChiKey: KEIBQKSSDDHMND-AQNXPRMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  109.98
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-But-3-enyl-N-[(1S,4S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohept-2-enyl]-2-nitro-benzenesulfonamide 在 吡啶 、 Grubbs catalyst first generation 、 potassium carbonate 、 甲基磺酰氯 、 苯硫酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 84.5h， 生成 benzyl (6S)-6-[2-[tert-butyl(dimethyl)silyl]oxy-3-[(6S)-1-phenylmethoxycarbonyl-3,6-dihydro-2H-pyridin-6-yl]propyl]-3,6-dihydro-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Anaferine Dihydrochloride by a Ruthenium-Catalysed Tandem Ring Rearrangement Metathesis

  摘要：

  A stereoselective synthesis of (-)-anaferine dihydrochloride has been developed. The bis(tetrahydropyridine) system 10 was formed by a tandem ring rearrangement metathesis of the chiral bis(but-3-enylamino)cycloheptene derivative 9. (-)-Anaferine dihydrochloride was obtained in 23% overall yield in eleven steps and its absolute configuration was confirmed as (R,R) by this total synthesis.

  DOI：

  10.1002/1099-0690(200208)2002:16<2855::aid-ejoc2855>3.0.co;2-1
• 作为产物：
  描述：

  (-)-(1S,3S,5S)-5-[N-(but-3-enyl)-N-(2-nitrobenzenesulfonyl)amino]-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enyl acetate 在 甲醇 、 potassium cyanide 作用下， 反应 15.0h， 以96%的产率得到N-But-3-enyl-N-[(1S,4S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohept-2-enyl]-2-nitro-benzenesulfonamide
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Anaferine Dihydrochloride by a Ruthenium-Catalysed Tandem Ring Rearrangement Metathesis

  摘要：

  A stereoselective synthesis of (-)-anaferine dihydrochloride has been developed. The bis(tetrahydropyridine) system 10 was formed by a tandem ring rearrangement metathesis of the chiral bis(but-3-enylamino)cycloheptene derivative 9. (-)-Anaferine dihydrochloride was obtained in 23% overall yield in eleven steps and its absolute configuration was confirmed as (R,R) by this total synthesis.

  DOI：

  10.1002/1099-0690(200208)2002:16<2855::aid-ejoc2855>3.0.co;2-1