(2S,3S,7aR)-2,3-Bis-(4-nitro-phenyl)-hexahydro-pyrrolo[2,1-b]oxazole | 117772-78-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3S,7aR)-2,3-Bis-(4-nitro-phenyl)-hexahydro-pyrrolo[2,1-b]oxazole
• 英文别名: rel-(2R,3R,7aS)-Hexahydro-2,3-bis(4-nitrophenyl)pyrrolo[2,1-b]oxazole；(2S,3S,7aR)-2,3-bis(4-nitrophenyl)-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b][1,3]oxazole
• CAS: 117772-78-8
• 化学式: C₁₈H₁₇N₃O₅
• 分子量: 355.35
• InChiKey: KBBLTOXLZJCAJA-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 L-脯氨酸 在 1,3-双[3,5-双(三氟甲基)苯基]硫脲 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以40%的产率得到(2S,3S,7aR)-2,3-Bis-(4-nitro-phenyl)-hexahydro-pyrrolo[2,1-b]oxazole
  参考文献：
  名称：

  脯氨酸催化的简单直接羟醛反应对手性环己酮的高度对映和非对映选择性有机催化脱对称

  摘要：

  醛醇缩合不对称的灵丹妙药：我们描述了脯氨酸催化的4取代环己酮的不对称化的简便方法，它使用不同的氢键供体作为助催化剂（参见方案），从而显着提高了脯氨酸在不对称化反应中的催化效率。

  DOI：

  10.1002/chem.200900488

文献信息

• Functionalization of an sp3 C–H bond via a redox-neutral domino reaction: diastereoselective synthesis of hexahydropyrrolo[2,1-b]oxazoles
  作者：Matiur Rahman、Avik Kumar Bagdi、Subhajit Mishra、Alakananda Hajra

  DOI：10.1039/c4cc00454j

  日期：——

  A diastereoselective synthesis of pyrrolidinooxazolidines was achieved by a metal-free, base-promoted reaction of pyrrolidine and aromatic aldehydes under microwave irradiation. The rare functionalization of an sp3 C–H bond probably results from an in situ generated azomethine ylide that undergoes cycloaddition with aldehydes.

  在微波辐照下，通过无金属、碱促进的吡咯烷和芳香醛反应，实现了吡咯烷类噁唑烷的非对映选择性合成。sp3 CâH 键的罕见官能化可能是由原位生成的偶氮甲基醯胺与醛发生环化反应的结果。
• Forte, Maurizio; Orsini, Fulvia; Pelizzoni, Francesca, Gazzetta Chimica Italiana, 1985, vol. 115, # 10, p. 569 - 572
  作者：Forte, Maurizio、Orsini, Fulvia、Pelizzoni, Francesca

  DOI：——

  日期：——
• Seebach’s oxazolidinone is a good catalyst for aldol reactions
  作者：Carles Isart、Jordi Burés、Jaume Vilarrasa

  DOI：10.1016/j.tetlet.2008.07.028

  日期：2008.9

  Seebach's proline-derived oxazolidinone 2d overcomes (S)-proline and is at least as efficient as (S)-5(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examined. A quick exchange takes place between 2d and carbonyl Compounds that gives new bicyclic oxazolidinones, in equilibrium with the very minor active species (enamines). Maximum yields of the aldols (beta-hydroxy ketones) were achieved after 1-4 h when, with proline, they are attained after 30-48 h. (c) 2008 Elsevier Ltd. All rights reserved.
• 1,3 Dipolar cycloadditions of azomethine ylides with aromatic aldehydes. syntheses of 1-oxapyrrolizidines and 1,3-oxazolidines.
  作者：F. Orsini、F. Pelizzoni、M. Forte、R. Destro、P. Gariboldi

  DOI：10.1016/s0040-4020(01)85842-7

  日期：1988.1
• Cerium(IV) oxide as a neutral catalyst for aldehyde-induced decarboxylative coupling of l-proline with triethyl phosphite and nitromethane
  作者：Habib Firouzabadi、Nasser Iranpoor、Arash Ghaderi、Maryam Ghavami

  DOI：10.1016/j.tetlet.2012.08.012

  日期：2012.10

  The application of cerium(IV) oxide (CeO2) as a neutral and heterogeneous catalyst for aldehyde-induced decarboxylative coupling of L-proline with triethyl phosphite and nitromethane is described. In addition, a [3+2] cycloaddition reaction of the in situ generated 1,3-dipolar intermediate with benzaldehyde in the absence of a nucleophile is also reported. (C) 2012 Published by Elsevier Ltd.