(5S)-2-hydroxy-5-(2-hydroxyethyl)-N'-(4-methoxy-2,3,6-trimethylphenyl)sulfonylpyrrolidine-1-carboximidamide | 316830-92-9

• 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: (5S)-2-hydroxy-5-(2-hydroxyethyl)-N'-(4-methoxy-2,3,6-trimethylphenyl)sulfonylpyrrolidine-1-carboximidamide
• CAS: 316830-92-9
• 化学式: C₁₇H₂₇N₃O₅S
• 分子量: 385.484
• InChiKey: XWZAUQLPFMQSEY-CFMCSPIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酰丙酮苄酯 、 (5S)-2-hydroxy-5-(2-hydroxyethyl)-N'-(4-methoxy-2,3,6-trimethylphenyl)sulfonylpyrrolidine-1-carboximidamide 在 2,2,2-三氟乙醇 、 乙酸吗啉 作用下， 反应 48.0h， 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 在 lead(IV) acetate 、 四氧化锇 、 N-甲基吲哚酮 、 氨 、 silver nitrate 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 21.0h， 生成 (5S)-2-hydroxy-5-(2-hydroxyethyl)-N'-(4-methoxy-2,3,6-trimethylphenyl)sulfonylpyrrolidine-1-carboximidamide
  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

文献信息

• Tuning Stereoselection in Tethered Biginelli Condensations. Synthesis of <i>cis</i>- or <i>trans</i>-1-Oxo- and 1-Iminohexahydropyrrolo[1,2-<i>c</i>]pyrimidines
  作者：Andrew I. McDonald、Larry E. Overman

  DOI：10.1021/jo981972g

  日期：1999.3.1

  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).