(1R,7R,8R)-4-amino-7-ethylsulfanyl-10,11-dioxa-5-thiatricyclo[6.2.1.0^2,6]undeca-2(6),3-diene-3-carbonitrile | 246148-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R,7R,8R)-4-amino-7-ethylsulfanyl-10,11-dioxa-5-thiatricyclo[6.2.1.0^2,6]undeca-2(6),3-diene-3-carbonitrile
• CAS: 246148-09-4
• 化学式: C₁₁H₁₂N₂O₂S₂
• 分子量: 268.36
• InChiKey: YAVDCHKIUPIFGA-AZTOOPQRSA-N

反应信息

• 作为反应物：
  描述：

  原甲酸三乙酯 、 (1R,7R,8R)-4-amino-7-ethylsulfanyl-10,11-dioxa-5-thiatricyclo[6.2.1.0^2,6]undeca-2(6),3-diene-3-carbonitrile 在 氨 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以68%的产率得到(1R,11R,12R)-11-ethylsulfanyl-5,7-diaza-14,15-dioxa-9-thiatetracyclo[10.2.1.0^2,10.0^3,8]pentadeca-2(10),3(8),4,6-tetraen-4-ylamine
  参考文献：
  名称：

  Synthesis of Anellated Pyranose Derivatives on the Basis of Levoglucosenone

  摘要：

  1,6-Anhydro-2-(dicyanomethylene)-2,3-dideoxy-4-S-ethyl-4-thio-beta-D-erythro-hexopyranose (1) reacted with tosyl azide or sulfur and triethylamine to furnish the 5-aza-10,11-dioxatricyclo[6.2.1.0(2,6)]undeca-2(6),3-diene-3-carbonitrile 2 and the 10,11-dioxa-5-thiatricyclo[6.2.1.0(2,6)]undeca-2(6),3-diene-3-carbonitrile 3, respectively. The reactions of 1 with arylisothiocyanates furnished the 11,12-dioxa-5-thiatricyclo[7.2.1.0(2,7)]dodeca-2(7),3 -diene-3-carbonitriles 4 and 5. 3 underwent cyclization with triethyl orthoformate and ammonia or hydrazine hydrate to afford the 5,7-diaza-14,15-dioxa-9-thiatetracyclo[10.2.1.0(2,10).0(3.8)]pentadecatetra(tri)enes 7 and 8, respectively.

  DOI：

  10.1080/07328309908544040
• 作为产物：
  描述：

  1,6-anhydro-2-(dicyanomethylene)-2,3-dideoxy-4-S-ethyl-4-thio-β-D-erythro-hexopyranose 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以58%的产率得到(1R,7R,8R)-4-amino-7-ethylsulfanyl-10,11-dioxa-5-thiatricyclo[6.2.1.0^2,6]undeca-2(6),3-diene-3-carbonitrile
  参考文献：
  名称：

  Synthesis of Anellated Pyranose Derivatives on the Basis of Levoglucosenone

  摘要：

  1,6-Anhydro-2-(dicyanomethylene)-2,3-dideoxy-4-S-ethyl-4-thio-beta-D-erythro-hexopyranose (1) reacted with tosyl azide or sulfur and triethylamine to furnish the 5-aza-10,11-dioxatricyclo[6.2.1.0(2,6)]undeca-2(6),3-diene-3-carbonitrile 2 and the 10,11-dioxa-5-thiatricyclo[6.2.1.0(2,6)]undeca-2(6),3-diene-3-carbonitrile 3, respectively. The reactions of 1 with arylisothiocyanates furnished the 11,12-dioxa-5-thiatricyclo[7.2.1.0(2,7)]dodeca-2(7),3 -diene-3-carbonitriles 4 and 5. 3 underwent cyclization with triethyl orthoformate and ammonia or hydrazine hydrate to afford the 5,7-diaza-14,15-dioxa-9-thiatetracyclo[10.2.1.0(2,10).0(3.8)]pentadecatetra(tri)enes 7 and 8, respectively.

  DOI：

  10.1080/07328309908544040