methyl 5-(S)-[2-(R)-(methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate | 418759-12-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-(S)-[2-(R)-(methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate
• 英文别名: methyl-5-(S)-[2-(S)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate；methyl (3S)-3-[(2S)-2-methoxycarbonylpyrrolidine-1-carbonyl]-2-(4-methylphenyl)-3,4-dihydropyrazole-5-carboxylate
• CAS: 418759-12-3
• 化学式: C₁₉H₂₃N₃O₅
• 分子量: 373.409
• InChiKey: KZCUBZWSXXCEFP-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 5-(S)-[2-(R)-(methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以75%的产率得到(3S)-3-[(2S)-2-carboxypyrrolidine-1-carbonyl]-2-(4-methylphenyl)-3,4-dihydropyrazole-5-carboxylic acid
  参考文献：
  名称：

  Diastereoselective cycloadditions of nitrilimines to enantiopure acrylamides

  摘要：

  The diastereoselective cycloaddition of the nitrilimine 2 with enantiopure acrylamides 3 was exploited to obtain enantiopure 4,5-dihydropyrazoles 4 and 5. Basic hydrolysis of the cycloadducts gave the dicarboxy derivatives 6 and 7 or 8 and 9, which are of potential interest as new chiral building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00258-6
• 作为产物：
  描述：

  methyl 2-chloro-2-(4-methylphenyl-hydrazono)acetate 、 N-acryloyl-L-proline methyl ester 在 silver(I) acetate 作用下， 以 甲苯 为溶剂， 反应 23.0h， 生成 methyl 5-(S)-[2-(S)-(methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate 、 methyl 5-(S)-[2-(R)-(methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate
  参考文献：
  名称：

  Diastereoselective cycloadditions of nitrilimines to enantiopure acrylamides

  摘要：

  The diastereoselective cycloaddition of the nitrilimine 2 with enantiopure acrylamides 3 was exploited to obtain enantiopure 4,5-dihydropyrazoles 4 and 5. Basic hydrolysis of the cycloadducts gave the dicarboxy derivatives 6 and 7 or 8 and 9, which are of potential interest as new chiral building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00258-6

文献信息

• The diastereoisomers methyl 5-(<i>S</i>)-[2-(<i>R</i>)/(<i>S</i>)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate
  作者：Tullio Pilati、Gianluigi Casalone

  DOI：10.1107/s0108270101021552

  日期：2002.3.15

  The title diastereoisomers, methyl 5-(S)-[2-(S)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methyl- phenyl)-4,5-dihydropyrazole-3-carboxylate and methyl 5-(S)[2-(R)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcar- bonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxyl- ate, both C19H23N3O5, have been studied in two crystalline forms. The first form, methyl 5-(S)-[2-(S)-methoxycarbonyl)2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)- 4,5-dihydropyrazole-3-carboxylate-methyl 5-(S)-[2-(R)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate (1/1), 2(S),5(S)-C19H23N3O5.2(R),5(S)-C19H23N3O5, contains both S,S and S,R isomers, while the second, methyl 5-(S)-[2-(S)methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]- 1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate, 2(S),5(S)-C19H23N3O5, is the pure S,S isomer. The S,S isomers in the two structures show very similar geometries, the maximum difference being about 15degrees on one torsion angle. The differences between the S,S and S,R isomers, apart from those due to the inversion of one chiral centre, are more remarkable, and are partially due to a possible rotational disorder of the 2-(methoxycarbonyl)tetrahydropyrrole group.
• Diastereoselective cycloadditions of nitrilimines to enantiopure acrylamides
  作者：Luisa Garanti、Giorgio Molteni、Tullio Pilati

  DOI：10.1016/s0957-4166(02)00258-6

  日期：2002.7

  The diastereoselective cycloaddition of the nitrilimine 2 with enantiopure acrylamides 3 was exploited to obtain enantiopure 4,5-dihydropyrazoles 4 and 5. Basic hydrolysis of the cycloadducts gave the dicarboxy derivatives 6 and 7 or 8 and 9, which are of potential interest as new chiral building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.