(2S,4R)-1,2-dibenzyloxycarbonyl-4-(prop-2-yn-1-yloxy)pyrrolidine | 1207279-60-4

• 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-(prop-2-yn-1-yloxy)pyrrolidine
• 英文别名: dibenzyl (2S,4R)-4-prop-2-ynoxypyrrolidine-1,2-dicarboxylate
• CAS: 1207279-60-4
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: RLWXJDCJFLXDES-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1,2-dibenzyloxycarbonyl-4-(prop-2-yn-1-yloxy)pyrrolidine 、 6A-叠氮基-6A-脱氧-β-环糊精 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以75%的产率得到6(I)-[[(2S,4R)-1,2-dibenzyloxycarbonylpyrrolidin-4-yl]4-oxymethyl]-1H-1,2,3-triazol-1-yl-6(I)-deoxy-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 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.33h， 以75%的产率得到(2S,4R)-1,2-dibenzyloxycarbonyl-4-(prop-2-yn-1-yloxy)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

• Synthesis of new ionic-liquid-tagged organocatalysts and their application in stereoselective direct aldol reactions
  作者：Sadaf S. Khan、Jabbar Shah、Jürgen Liebscher

  DOI：10.1016/j.tet.2010.04.115

  日期：2010.7

  and subsequent N-methylation. These products were applied as ionic-liquid-tagged organocatalysts in asymmetric direct aldol reactions. Remarkably, a lysine-derived conjugate performed better than proline derivatives. Evidence was found that IL-tagging improved the catalytic performance. Recycling of the organocatalyst was easily possible by extraction of products.

  通过铜催化的炔-叠氮化物环加成反应和随后的N-甲基化反应，在氨基酸上形成1,2,3-三唑鎓单元，从而合成了新的氨基酸1,2,3-三唑鎓共轭物。这些产物在不对称直接羟醛反应中用作离子液体标记的有机催化剂。值得注意的是，赖氨酸衍生的缀合物的性能优于脯氨酸衍生物。有证据表明IL标记改善了催化性能。通过提取产物很容易实现有机催化剂的再循环。
• 1,2,3-Triazolium-Tagged Prolines and Their Application in Asymmetric Aldol and Michael Reactions
  作者：Jürgen Liebscher、Jabbar Shah、Sadaf Khan、Haiko Blumenthal

  DOI：10.1055/s-0029-1217039

  日期：2009.12

  Novel 1,2,3-triazolium-tagged proline derivatives were synthesized by copper-catalyzed click-reaction of alkynes with azides and N-alkylation of the resulting 1,2,3-triazoles. They were applied as recyclable organocatalysts in direct asymmetric aldol and Michael reactions with high enantioselectivity and diastereoselectivity. These catalysts performed better than (S)-proline itself; that is to say

  通过炔烃与叠氮化物的铜催化点击反应和所得1,2,3-三唑的N-烷基化反应，合成了新的1,2,3-三唑鎓标记的脯氨酸衍生物。它们被用作具有高对映选择性和非对映选择性的直接不对称羟醛和迈克尔反应中的可回收有机催化剂。这些催化剂的性能优于（S）-脯氨酸本身。也就是说，存在三唑鎓和脯氨酸部分的协同作用。反应可以在常规溶剂中或在离子液体中进行。催化剂易于回收再利用多次。 Aldol反应-Michael反应-不对称合成-有机催化-离子液体-点击反应
• Corrigendum to “Synthesis of new ionic-liquid-tagged organocatalysts and their application in stereoselective direct aldol reactions” [Tetrahedron 66 (27–28) (2010) 5082–5088]
  作者：Sadaf S. Khan、Jabbar Shah、Jürgen Liebscher

  DOI：10.1016/j.tet.2010.09.107

  日期：2010.11
• 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.