1,6-anhydro-2-(dicyanomethylene)-2,3-dideoxy-4-S-ethyl-4-thio-β-D-erythro-hexopyranose | 221089-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-2-(dicyanomethylene)-2,3-dideoxy-4-S-ethyl-4-thio-β-D-erythro-hexopyranose
• CAS: 221089-18-5
• 化学式: C₁₁H₁₂N₂O₂S
• 分子量: 236.294
• InChiKey: SRXCHVRWEOXYII-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  66.04
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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 2.5h， 生成 (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：

  丙二腈 、 1,6-anhydro-3-deoxy-4-S-ethyl-4-thio-β-D-erythro-hexopyranos-2-ulose 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以62%的产率得到1,6-anhydro-2-(dicyanomethylene)-2,3-dideoxy-4-S-ethyl-4-thio-β-D-erythro-hexopyranose
  参考文献：
  名称：

  Synthesis of Push-Pull Derivatives of Levoglucosenone as Precursors of Annellated Pyranosides

  摘要：

  1,6-Anhydro-3-deoxy-4-S-ethyl-4-thio-beta-D-erythro-hexopyranos-2-ulose (2) reacted with carbon disulphide and iodomethane to furnish 1,6-anhydro-3-[bis(methylthio)methylene]-3-deoxy-4-S-ethyl-4-thio-beta-D-erythro-hexopyranos-2-ulose (3). Treatment of 2 with dimethylformamide dimethyl acetal yielded 1,6-anhydro-3-deoxy-3-(dimethylaminomethylene)-4-S-ethyl-4-thio-beta-D-erythro-hexopyranos-2-ulose (4). The reactions of 3 with malononitrile and hydrazine hydrate furnished 1,6-anhydro-3-[bis-(methylthio)methylene]-2-(dicyanomethylene)-2,3-dideoxy-4-S-ethyl-4-thio-beta-D-erythro-hexopyranose (7) and (1R,7R,8R)-2,3,5,6(2,4,5,6)-tetradehydro-7-ethylthio-5- methylthio-3,4-diaza-10,11-dioxatricyclo[6.2.1.0(2,6)]undecane (8a, b), respectively.

  DOI：

  10.1080/07328309908543979