N-[1-[(S)-1-(2-Hydroxy-ethyl)-5-methyl-hex-4-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide | 221493-39-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-[1-[(S)-1-(2-Hydroxy-ethyl)-5-methyl-hex-4-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide
• CAS: 221493-39-6
• 化学式: C₂₁H₃₄N₂O₄S₂
• 分子量: 442.644
• InChiKey: WYFGWFHUAPTMIO-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  87.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[1-[(S)-1-(2-Hydroxy-ethyl)-5-methyl-hex-4-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide 在 lead(IV) acetate 、 四氧化锇 、 N-甲基吲哚酮 、 2,2,2-三氟乙醇 、 氨 、 乙酸吗啉 、 silver nitrate 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 67.0h， 生成 benzyl (4aR,7S)-7-(2-hydroxyethyl)-1-(4-methoxy-2,3,6-trimethylphenyl)sulfonylimino-3-methyl-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-c]pyrimidine-4-carboxylate
  参考文献：
  名称：

  Tuning Stereoselection in Tethered Biginelli Condensations. Synthesis of cis- or trans-1-Oxo- and 1-Iminohexahydropyrrolo[1,2-c]pyrimidines

  摘要：

  Stereoselection in tethered Biginelli condensations can be tuned to give either the cia or trans stereoisomer of 1-oxohexahydropyrrolo[1,2-c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).

  DOI：

  10.1021/jo981972g
• 作为产物：
  描述：

  (S)-3-amino-7-methyl-6-octen-1-ol 、 S,S-dimethyl N-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-carbonimidodithioate 以 苯 为溶剂， 反应 2.0h， 以77%的产率得到N-[1-[(S)-1-(2-Hydroxy-ethyl)-5-methyl-hex-4-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide
  参考文献：
  名称：

  Tuning Stereoselection in Tethered Biginelli Condensations. Synthesis of cis- or trans-1-Oxo- and 1-Iminohexahydropyrrolo[1,2-c]pyrimidines

  摘要：

  Stereoselection in tethered Biginelli condensations can be tuned to give either the cia or trans stereoisomer of 1-oxohexahydropyrrolo[1,2-c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).

  DOI：

  10.1021/jo981972g