ethyl 2-((2S,4R,5S)-4-amino-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate | 1429516-69-7

• 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: ethyl 2-((2S,4R,5S)-4-amino-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate
• 英文别名: ethyl 2-[(2S,4R,5S)-4-amino-5-(3,5-dimethoxyphenyl)-1-(4-methylphenyl)sulfonylpyrrolidin-2-yl]acetate
• CAS: 1429516-69-7
• 化学式: C₂₃H₃₀N₂O₆S
• 分子量: 462.567
• InChiKey: RMJDOXUTMACQDT-LXBDKUERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-((2S,4R,5S)-4-amino-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate 在 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 ethyl 2-((2S,3aR,9bS)-4-benzyl-6,8-dimethoxy-1-tosyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]isoquinolin-2-yl)acetate
  参考文献：
  名称：

  A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade

  摘要：

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.

  DOI：

  10.1021/ol4006129
• 作为产物：
  描述：

  N-(3,5-dimethoxybenzylidene)-4-methylbenzenesulfonamide 在 palladium on activated charcoal 、 C₃₅H₄₇N₃O₂ 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 ethyl 2-((2S,4R,5S)-4-amino-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate
  参考文献：
  名称：

  A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade

  摘要：

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.

  DOI：

  10.1021/ol4006129

文献信息

• A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade
  作者：Tao Cheng、Sixuan Meng、Yong Huang

  DOI：10.1021/ol4006129

  日期：2013.4.19

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.