7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane | 884588-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane
• 英文别名: (7-aza-bicyclo[4.1.0]hept-7-yl)-(3,5-dinitro-phenyl)-methanone；7-Azabicyclo[4.1.0]heptan-7-yl-(3,5-dinitrophenyl)methanone
• CAS: 884588-09-4
• 化学式: C₁₃H₁₃N₃O₅
• 分子量: 291.263
• InChiKey: KWJNKJYVTMQZAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane 在 (1R,2R)-2-(tert-butyldiphenylsilyloxy)-N-(dipyrrolidin-1-ylmethylene)-2,3-dihydro-1H-inden-1-amine 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 72.75h， 生成 (R)-N-(cyclohex-2-enyl)-3,5-dinitrobenzamide
  参考文献：
  名称：

  Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

  摘要：

  一种氨基-吲哚衍生的手性胍被开发作为高效的Brønsted碱催化剂，用于与硫醇和氨基二硫酸作为核苷酸的meso-亚胺环的去对称化，提供高产率和对映选择性的1,2-双功能化开环产物。

  DOI：

  10.1039/c0cc05840h
• 作为产物：
  描述：

  trans-2-azido-1-cyclohexanol 、 3,5-二硝基苯甲酰氯 在 三苯基膦 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane
  参考文献：
  名称：

  α,α-二芳基-L-脯氨醇促进内消旋-N-酰基氮丙啶与苯硫醇的去对称化

  摘要：

  公开了 α,α-二芳基-L-脯氨醇以促进内消旋-N-酰基氮丙啶与苯硫醇的去对称化，从而以良好的收率和适中的对映选择性（高达 61 % ee）提供产品，可以大大提高到 > 90 % ee 单次重结晶后。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900095

文献信息

• Enantioselective ring-opening of aziridines
  申请人：Antilla Jon C.

  公开号：US20090030212A1

  公开（公告）日：2009-01-29

  A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst

  一种制备环氧丙烷和亲核试剂的亲核加成产物的方法，该方法包括在双芳基磷酸催化剂存在下处理环氧丙烷和亲核试剂。
• Mg^II -Catalyzed Desymmetrization Reaction of <i>meso</i> -Aziridines with Hydroxylamines: Synthesis of Novel Chiral 1,2-Diamine Skeletons
  作者：Dan Li、Dongxu Yang、Linqing Wang、Xihong Liu、Xianxing Jiang、Rui Wang

  DOI：10.1002/chem.201603898

  日期：2016.11.21

  for the first time. A series of novel chiral 1,2‐diamine skeletons were obtained in good yields and enantioselectivities. The reaction employed magnesium catalysis generated in situ from a simple oxazoline‐OH chiral ligand. Obviously, the diverse structures of the obtained chiral 1,2‐diamine compounds could allow them to be potential chiral ligands in future catalytic asymmetric synthesis studies.

  首次公开了Mg II催化的内消旋氮丙啶与羟胺的脱对称反应。以良好的收率和对映选择性获得了一系列新颖的手性1,2-二胺骨架。该反应采用由简单的恶唑啉-OH手性配体原位生成的镁催化。显然，获得的手性1,2-二胺化合物的不同结构可能使它们成为未来催化不对称合成研究中潜在的手性配体。
• Gram-Scale Preparation of VAPOL Hydrogenphosphate: A Structurally Distinct Chiral Brønsted Acid
  作者：William Wulff、Aman Desai、Li Huang、Gerald Rowland、Jon Antilla

  DOI：10.1055/s-0029-1218783

  日期：2010.6

  A detailed gram-scale synthesis of VAPOL hydrogenphosphate, a structurally distinct chiral Brønsted acid, is presented. The reaction utilizes commercially available starting materials, proceeds with high yields and has been reproduced numerous times at scale.

  本文详细介绍了VAPOL磷酸氢盐的克级合成，这是一种结构独特的布伦斯特手性酸。该反应利用市售的原料，收率高，并已多次大规模复制。
• Chiral Phosphoric Acid-Catalyzed Desymmetrization of <i>meso</i>-Aziridines with Functionalized Mercaptans
  作者：Shawn E. Larson、Juan C. Baso、Guilong Li、Jon C. Antilla

  DOI：10.1021/ol902123h

  日期：2009.11.19

  Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction.
• Studies on the true catalyst in the phosphate-promoted desymmetrization of meso-aziridines with silylated nucleophiles
  作者：Giorgio Della Sala

  DOI：10.1016/j.tet.2012.10.068

  日期：2013.1

  Significant amounts of metal phosphate impurities have been detected by NMR spectroscopy and ICP-OES analysis of synthetic, as well as purchased, samples of VAPOL hydrogen phosphate purified on silica gel. The previously reported VAPOL hydrogen phosphate-catalyzed desymmetrization of meso-aziridines with different silylated compounds, has been re-examined. While metal-free phosphoric acid exhibited low activity and enantioselectivity, calcium and magnesium phosphate salts proved to be the true catalysts in these related processes. Reproducible high enantioselectivities were obtained in the ring-opening of cyclic meso-aziridines with Me3SiX (X=SPh, SePh, N-3) employing a 1:1 mixture of calcium and magnesium VAPOL phosphates. The reaction has been successfully extended to Me3SiSBn, Me3SiSMe and Me3SiNCS, giving ring-opened products in high yield and unprecedented moderate to good enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.