(2S,4R)-1,2-dibenzyloxycarbonyl-4-(1H-imidazol-1-carbonyloxy)pyrrolidine | 1393739-72-4

• 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: (2S,4R)-1,2-dibenzyloxycarbonyl-4-(1H-imidazol-1-carbonyloxy)pyrrolidine
• 英文别名: dibenzyl (2S,4R)-4-(imidazole-1-carbonyloxy)pyrrolidine-1,2-dicarboxylate
• CAS: 1393739-72-4
• 化学式: C₂₄H₂₃N₃O₆
• 分子量: 449.463
• InChiKey: WNCBDSZTKYYQMS-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1,2-dibenzyloxycarbonyl-4-(1H-imidazol-1-carbonyloxy)pyrrolidine 、 6(I)-amino-6(I)-deoxy-(2I-VII),3(I-VII),6(II-VII)-eicosakis-O-benzyl-β-cyclodextrin 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以83%的产率得到6(I)-[(2S,4R)-1,2-dibenzyloxycarbonylpyrrolidin-4-yl]-oxycarbonylamino-6(I)-deoxy-2(I-VII),3(I-VII),6(II-VII)-eicosakis-obenzyl-β-cyclodextrin
  参考文献：
  名称：

  Proline–cyclodextrin conjugates: synthesis and evaluation as catalysts for aldol reaction in water

  摘要：

  The synthesis of six conjugates of L-proline and beta-cyclodextrin and their evaluation as catalysts of aldol reaction in water are described. The results indicated that the nature of the linker between proline and beta-cyclodextrin is important for catalytic activity: the one with the most flexible linker gave the best results. Inhibition experiments showed that the cavity of beta-cyclodextrin plays a role in the catalysis. Permethylation of the cyclodextrin hydroxyl groups led to higher conversion rates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.089
• 作为产物：
  描述：

  (2s,4r)-1,2-二苄氧羰基-4-羟基吡咯烷 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到(2S,4R)-1,2-dibenzyloxycarbonyl-4-(1H-imidazol-1-carbonyloxy)pyrrolidine
  参考文献：
  名称：

  Proline–cyclodextrin conjugates: synthesis and evaluation as catalysts for aldol reaction in water

  摘要：

  The synthesis of six conjugates of L-proline and beta-cyclodextrin and their evaluation as catalysts of aldol reaction in water are described. The results indicated that the nature of the linker between proline and beta-cyclodextrin is important for catalytic activity: the one with the most flexible linker gave the best results. Inhibition experiments showed that the cavity of beta-cyclodextrin plays a role in the catalysis. Permethylation of the cyclodextrin hydroxyl groups led to higher conversion rates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.089

文献信息

• Proline–cyclodextrin conjugates: synthesis and evaluation as catalysts for aldol reaction in water
  作者：Elisa G. Doyagüez、Alfonso Fernández-Mayoralas

  DOI：10.1016/j.tet.2012.06.089

  日期：2012.9

  The synthesis of six conjugates of L-proline and beta-cyclodextrin and their evaluation as catalysts of aldol reaction in water are described. The results indicated that the nature of the linker between proline and beta-cyclodextrin is important for catalytic activity: the one with the most flexible linker gave the best results. Inhibition experiments showed that the cavity of beta-cyclodextrin plays a role in the catalysis. Permethylation of the cyclodextrin hydroxyl groups led to higher conversion rates. (C) 2012 Elsevier Ltd. All rights reserved.