3,4-diisopropyl 2-methyl (2S,3S,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate | 1062148-79-1

• 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: 3,4-diisopropyl 2-methyl (2S,3S,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate
• 英文别名: 3,4-diisopropyl 2-methyl (2S,3S,4S,5R)-5-phenyl-2,3,4-pyrrolidinetricarboxylate；2-O-methyl 3-O,4-O-dipropan-2-yl (2S,3S,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate
• CAS: 1062148-79-1
• 化学式: C₂₀H₂₇NO₆
• 分子量: 377.437
• InChiKey: CFOZKZLEEWCINP-QAETUUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  富马酸二异丙酯 、 [(苯基甲亚基)氨基]乙酸甲酯 在 (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine 、 silver perchlorate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 3,4-diisopropyl 2-methyl (2S,3S,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylate 、 3,4-diisopropyl 2-methyl (2R,3R,4R,5S)-5-phenyl-2,3,4-pyrrolidinetricarboxylate
  参考文献：
  名称：

  手性亚磷酰胺-银(I)配合物催化偶氮甲碱叶立德和烯烃的对映选择性1,3-偶极环加成合成脯氨酸

  摘要：

  这项工作得到了西班牙教育部长 (MEC) DGES (Consolider INGENIO 2010 CSD2007-00006、CTQ2007-62771/BQU 和 CTQ2004-00808/BQU) 和阿利坎特大学的支持。

  DOI：

  10.1002/ejoc.200900774

文献信息

• Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions
  作者：Carmen Nájera、M. de Gracia Retamosa、José M. Sansano、Abel de Cózar、Fernando P. Cossío

  DOI：10.1016/j.tetasy.2008.12.021

  日期：2008.12

  The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the experimentally observed high enantio- and endo-selectivity through a very asynchronous transition state. (C) 2009 Elsevier Ltd. All rights reserved.
• Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
  作者：Ihssene Chabour、Luis M. Castelló、Juan Mancebo-Aracil、María Martín-Rodríguez、María de Gracia Retamosa、Carmen Nájera、José M. Sansano

  DOI：10.1016/j.tetasy.2017.08.011

  日期：2017.10

  The asymmetric 1,3-dipolar cycloaddition of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite 14 center dot AgClO4 complex. (C) 2017 Elsevier Ltd. All rights reserved.
• Catalytic Enantioselective 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides and Alkenes by Using Phosphoramidite-Silver(I) Complexes
  作者：Carmen Nájera、M. de Gracia Retamosa、José M. Sansano

  DOI：10.1002/anie.200801690

  日期：2008.7.28