7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]hept-3-ene

• 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]hept-3-ene
• 英文别名: 7-Azabicyclo[4.1.0]hept-3-en-7-yl-(3,5-dinitrophenyl)methanone
• 化学式: C₁₃H₁₁N₃O₅
• 分子量: 289.247
• InChiKey: VIDBNXIBXCGQED-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：
  0.31
• 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]hept-3-ene 在 6-deoxy-6-(diphenylphosphoryl)-arabino-hexitol-based ligand 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 2,6-二甲基苯酚 、 yttrium(III) isopropoxide 、 叠氮基三甲基硅烷 、 碘 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 53.0h， 生成 tert-butyl (1R,5S,6S)-6-acetylamino-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-ene-4-carboxylate
  参考文献：
  名称：

  Second Generation Catalytic Asymmetric Synthesis of Tamiflu:  Allylic Substitution Route

  摘要：

  Catalytic asymmetric synthesis of Tamiflu, an important antiinfluenza drug, was achieved. After the catalytic enantioselective desymmetrization of meso-aziridine 3 with TMSN3, using a Y catalyst (1 mol %) derived from ligand 2, an allylic oxygen function and C1 unit on the CC double bond were introduced through cyanophosphorylation of enone and allylic substitution with an oxygen nucleophile. This second generation route of Tamiflu is more practical than our previously reported route.

  DOI：

  10.1021/ol062663c
• 作为产物：
  描述：

  7-azabicyclo[4.1.0]hept-3-ene 、 3,5-二硝基苯甲酰氯 在 3,5-二硝基苯甲酰氯 作用下， 以85% over two steps的产率得到7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]hept-3-ene
  参考文献：
  名称：

  J. Am. Chem. Soc. 2006, 128, 6312-6313

  摘要：

  DOI：

文献信息

• Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines
  作者：Yan Zhang、Choon Wee Kee、Richmond Lee、Xiao Fu、Julian Ying-Teck Soh、Esther Mun Foong Loh、Kuo-Wei Huang、Choon-Hong Tan

  DOI：10.1039/c0cc05840h

  日期：——

  An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities.

  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。
• 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.
• J. Org. Chem. 2004, 69, 6128-6130
  作者：

  DOI：——

  日期：——
• Org. Lett. 2007, 9, 259-262
  作者：

  DOI：——

  日期：——
• Second Generation Catalytic Asymmetric Synthesis of Tamiflu:  Allylic Substitution Route
  作者：Tsuyoshi Mita、Nobuhisa Fukuda、Francesc X. Roca、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ol062663c

  日期：2007.1.1

  Catalytic asymmetric synthesis of Tamiflu, an important antiinfluenza drug, was achieved. After the catalytic enantioselective desymmetrization of meso-aziridine 3 with TMSN3, using a Y catalyst (1 mol %) derived from ligand 2, an allylic oxygen function and C1 unit on the CC double bond were introduced through cyanophosphorylation of enone and allylic substitution with an oxygen nucleophile. This second generation route of Tamiflu is more practical than our previously reported route.