(+/-)-2-acetoxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione | 193540-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (+/-)-2-acetoxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione
• CAS: 193540-63-5
• 化学式: C₁₅H₁₅N₃O₄
• 分子量: 301.302
• InChiKey: MTLFQZYOMBEPLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.23
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2-acetoxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 72.0h， 生成 、
  参考文献：
  名称：

  1-Azafagomine: A Hydroxyhexahydropyridazine That Potently Inhibits Enzymatic Glycoside Cleavage

  摘要：

  Abstract(3,4‐trans‐4,5‐trans)‐4,5‐dihydroxy‐3‐hydroxymethylhexahydropyrida‐zine (16) was synthesized in four steps from 2,4‐pentadienol (22) and 4‐phenyl‐triazolin‐3,5‐dione (18) in an overall yield of 32%. In the first step a Diels‐Alder reaction between 18 and 22 gave (π)‐2‐hydroxymethyl‐8‐phenyl‐1,6,8‐triazabicyclo[4.3.0]non‐3‐ene‐7,9‐dione (23c) in 88% yield. Epoxidation of 23c with trifluoromethyl(methyl)dioxirane, generated in situ, gave the trans epoxide 24c in 62% yield. Hydrolysis of the epoxide with perchloric acid gave stereoselectively (2,3‐trans‐3,4‐trans)‐3,4‐dihydroxy‐2‐hydroxy‐methyl‐8‐phenyl‐1,6,8‐triazabicyclo[4.3.0]‐nonane‐7,9‐dione (26) in 73% yield. In the fourth and final step, hydrazinolysis of 26 gave 16 in 84% yield. Pyridazine 16 was found to be a potent inhibitor of α‐and β‐glucosidase, isomaltase and glyco‐gen phosphorylase, while galactosidases and α‐mannosidase were not inhibited. The inhibition of β‐glucosidase is independent of pH, and was found to be due to unprotonated 16.

  DOI：

  10.1002/chem.19970030616
• 作为产物：
  描述：

  4-苯基脲唑 在 吡啶 、 次氯酸叔丁酯 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 36.58h， 生成 (+/-)-2-acetoxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione
  参考文献：
  名称：

  1-Azafagomine: A Hydroxyhexahydropyridazine That Potently Inhibits Enzymatic Glycoside Cleavage

  摘要：

  Abstract(3,4‐trans‐4,5‐trans)‐4,5‐dihydroxy‐3‐hydroxymethylhexahydropyrida‐zine (16) was synthesized in four steps from 2,4‐pentadienol (22) and 4‐phenyl‐triazolin‐3,5‐dione (18) in an overall yield of 32%. In the first step a Diels‐Alder reaction between 18 and 22 gave (π)‐2‐hydroxymethyl‐8‐phenyl‐1,6,8‐triazabicyclo[4.3.0]non‐3‐ene‐7,9‐dione (23c) in 88% yield. Epoxidation of 23c with trifluoromethyl(methyl)dioxirane, generated in situ, gave the trans epoxide 24c in 62% yield. Hydrolysis of the epoxide with perchloric acid gave stereoselectively (2,3‐trans‐3,4‐trans)‐3,4‐dihydroxy‐2‐hydroxy‐methyl‐8‐phenyl‐1,6,8‐triazabicyclo[4.3.0]‐nonane‐7,9‐dione (26) in 73% yield. In the fourth and final step, hydrazinolysis of 26 gave 16 in 84% yield. Pyridazine 16 was found to be a potent inhibitor of α‐and β‐glucosidase, isomaltase and glyco‐gen phosphorylase, while galactosidases and α‐mannosidase were not inhibited. The inhibition of β‐glucosidase is independent of pH, and was found to be due to unprotonated 16.

  DOI：

  10.1002/chem.19970030616