(2S,4S)-4-azido-1-benzyloxycarbonyl-2-tert-butylaminocarbonylpyrrolidine | 176047-29-3

• 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: (2S,4S)-4-azido-1-benzyloxycarbonyl-2-tert-butylaminocarbonylpyrrolidine
• 英文别名: (2S,4S)-4-azido-1-benzyloxycarbonyl-2-(t-butylaminocarbonyl)pyrrolidine；benzyl (2S,4S)-4-azido-2-(tert-butylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 176047-29-3
• 化学式: C₁₇H₂₃N₅O₃
• 分子量: 345.401
• InChiKey: OBVGHHPUEYRDDQ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-azido-1-benzyloxycarbonyl-2-tert-butylaminocarbonylpyrrolidine 在 palladium on activated charcoal 氢气 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 35.0h， 生成 (2S,4S)-2-tert-butylaminocarbonyl-4-(3-triethoxysilylpropylaminocarbonylamino)pyrrolidine
  参考文献：
  名称：

  固定脯氨酸在介孔载体上的不对称羟醛反应

  摘要：

  已经研究了在加热和微波的辅助下，使用固定化脯氨酸固定在介孔载体上羟丙酮与不同醛的醛醇缩合反应。发现在亲水性和疏水性溶剂中，MCM-41上均质化的L-脯氨酸催化醛醇缩合反应，并且在某些情况下提供了与均相催化剂互补的立体选择性。该多相催化剂可以重复使用而不会显着损失立体选择性。

  DOI：

  10.1002/adsc.200505058
• 作为产物：
  描述：

  (2S,4R)-1-benzyloxycarbonyl-2-tert-butylaminocarbonyl-4-hydroxypyrrolidine 在 sodium azide 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 (2S,4S)-4-azido-1-benzyloxycarbonyl-2-tert-butylaminocarbonylpyrrolidine
  参考文献：
  名称：

  固定脯氨酸在介孔载体上的不对称羟醛反应

  摘要：

  已经研究了在加热和微波的辅助下，使用固定化脯氨酸固定在介孔载体上羟丙酮与不同醛的醛醇缩合反应。发现在亲水性和疏水性溶剂中，MCM-41上均质化的L-脯氨酸催化醛醇缩合反应，并且在某些情况下提供了与均相催化剂互补的立体选择性。该多相催化剂可以重复使用而不会显着损失立体选择性。

  DOI：

  10.1002/adsc.200505058

文献信息

• Heterogenised catalysts on zeolites. Synthesis of new chiral Rh(I) complexes with (2S,4R)-trans-4-RCOO-2-(t-butylaminocarbonyl) pyrrolidines and (2S,4S)-cis-4-RCONH-2-(t-butylaminocarbonyl) pyrrolidines. Heterogenisation on silica and a USY-zeolite and study of the role of support on their catalytic profile in hydrogenation of olefins
  作者：A. Corma、M. Iglesias、F. Mohino、F. Sánchez

  DOI：10.1016/s0022-328x(97)00321-5

  日期：1997.10

  Novel chiral ligands (2S,4R)-2-(t-butylaminocarbonyl)-4-[3-(alkylaminocarbonyl)propanoyloxy]pyrrolidine and (2S,4S)-cis-4-(alkylaminocarbonylamino)-2-(t-butyl-aminocarbonyl)pyrrolidine (4a,b; 9a,b), (a: alkyl = t-butyl; b: alkyl = 3-triethoxysilylpropyl) and their rhodium complexes were synthesised and characterised. The reactions of [Rh(cod)Cl}(2)] and [RhCl(PPh3)(3)] with the chiral ligands in the presence of a non-coordinating anion (PF6-) gave the cationic complexes [Rh(L-2)(ligand)][PF6] (L-2 = cod, PPh3). The structures of these complexes were elucidated by elemental analyses, IR spectroscopy and H-1, C-13 and P-31 NMR measurements. The metal complexes bearing a triethoxysilyl group were covalently bonded to silica and modified USY-zeolite and Rh-heterogenised complexes were obtained. A comparative study (homogeneous versus supported) was made for the catalytic activity in hydrogenation reactions. (C) 1997 Elsevier Science S.A.
• New mono- and polyazafulleroids C60(NR)n (n=1,2,4,6) derived from a chiral azide containing N- and O-donor groups, and reactivity with [RhCl(CO)2]2
  作者：Marta Iglesias、Berta Gómez-Lor、Amelia Santos

  DOI：10.1016/s0022-328x(99)00657-9

  日期：2000.4

  Reactions in a 1:1 molar ratio of the chiral azide (2S,4S)-4-azido-1-benzyloxycarbonyl-2-((t)butylaminocarbonyl)pyrrolidine (N3R, R = C17H23N2O3, 1) with C-60 in ClPh, in the temperature range 100- 132 degrees C, lead to mixtures of mono- and polyazafulleroid species of general formula C-60(NR)(n) (n = 1, 2, 4), with a composition depending on the reaction conditions, and with a yield in the most substituted polyazafulleroids that increases with the concentration of reactants. However the reaction in a 1:6 molar ratio (fullerene-azide 1) leads only to hexaazafulleroids C-60(NR)(6). AU mono- and polyazafulleroids C-60(NR)(n) react with [Rh(CO)(2)Cl](2) to give complexes of composition C-60(NR)(n)[Rh(CO)(2)Cl](n), which could be used as catalysts in asymmetric hydrogenation of prochiral olefins. (C) 2000 Elsevier Science S.A. All rights reserved.
• Asymmetric Aldol Reaction Using Immobilized Proline on Mesoporous Support
  作者：Félix Calderón、Raquel Fernández、Félix Sánchez、Alfonso Fernández-Mayoralas

  DOI：10.1002/adsc.200505058

  日期：2005.8

  The aldol reaction of hydroxyacetone with different aldehydes using immobilized proline on a mesoporous support, assisted by heat and microwaves, has been explored. It was found that heterogenized L-proline on MCM-41 catalyzed aldol reactions in both hydrophilic and hydrophobic solvents, and provided stereoselectivities in some cases complementary to the homogeneous catalyst. The heterogeneous catalysts

  已经研究了在加热和微波的辅助下，使用固定化脯氨酸固定在介孔载体上羟丙酮与不同醛的醛醇缩合反应。发现在亲水性和疏水性溶剂中，MCM-41上均质化的L-脯氨酸催化醛醇缩合反应，并且在某些情况下提供了与均相催化剂互补的立体选择性。该多相催化剂可以重复使用而不会显着损失立体选择性。