methyl 7-(4-methylphenyl)-1-(4-chlorophenyl)-6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl 7-(4-methylphenyl)-1-(4-chlorophenyl)-6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylate
• 英文别名: methyl 1-(4-chlorophenyl)-6,8-dioxo-7-(4-tolyl)-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylate；methyl 6a-(4-chlorophenyl)-5-(4-methylphenyl)-4,6-dioxo-1,3a-dihydropyrrolo[3,4-c]pyrazole-3-carboxylate
• 化学式: C₂₀H₁₆ClN₃O₄
• 分子量: 397.818
• InChiKey: YWMVQUPTAZPIKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7-(4-methylphenyl)-1-(4-chlorophenyl)-6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylate 在 氯 作用下， 以 1,2-二氯乙烷 为溶剂， 以91%的产率得到(1R,5R,6R)-6-Chloro-1-(4-chloro-phenyl)-2,4-dioxo-3-p-tolyl-3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid methyl ester
  参考文献：
  名称：

  摘要：

  Substituted 2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylic acid esters react with chlorine and bromine to give the corresponding 4-halo-2,3,7-triazabicyclo[3.3.0]oct-2-ene-4-carboxylates. Heating of the latter to 120 degreesC under reduced pressure leads to elimination of nitrogen molecule and formation of 6-halo-3-azabicyclo[3.1.0]hexane-5-carboxylates.

  DOI：

  10.1023/a:1012354223760

文献信息

• A new synthetic route to substituted 1-fluoro-1-cyclopropanecarboxylates
  作者：Alexander P. Molchanov、Alexander V. Stepakov、Vitalii M. Boitsov、Rafael R. Kostikov

  DOI：10.1016/s0022-1139(01)00560-7

  日期：2002.3

  Substituted 6-fluoro-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylates were obtained as a mixture of the exo- and endo-isomers by reaction of substituted 6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-3-en-4-carboxylates with N-fluoropyridinium tetrafluoroborate.

  取代的6-氟-2,4-二氧代-3-氮杂双环得到作为混合物[3.1.0]己烷-6-羧酸盐外-和内-异构体通过的反应取代的6,8-二氧代-2,3- ，N-氟吡啶鎓四氟硼酸酯具有7，7-三氮杂双环[3.3.0] oct-3-en-4-羧酸盐。
• ——
  作者：A. P. Molchanov

  DOI：10.1023/a:1023407032225

  日期：——

  Substituted methyl 2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylates and 1,2,7-triazaspiro[4.4]-non-2-ene-3-carboxylates react with N-iodosuccinimide (or the system iodine-silver trifluoroacetate) to give, respectively, methyl 6-iodo-3-azabicyclo[3.1.0]hexane-6-carboxylates or methyl 1-iodo-4,6-dioxo-5-azaspiro-[2.4]heptane-1-carboxylates as mixtures of exo and endo isomers.
• ——
  作者：A. P. Molchanov、A. V. Stepakov、V. M. Boitsov、J. Kopf、R. R. Kostikov

  DOI：10.1023/a:1022575932070

  日期：——

  Substituted 6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylates react with N-fluoropyridinium tetrafluoroborate to give mixtures of exo and endo isomers of 6-fluoro-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylates. Analogous reaction of 6,8-dioxo-1,2,7-triazaspiro[4.4]non-2-ene-3-carboxylates results in formation of syn,anti-isomeric 1-fluoro-4,6-dioxo-5-azaspiro[2.4]heptane-1-carboxylates.