(4S,5S)-5,8-dimethyl-4-hydroxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione | 204331-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并哒嗪类
• 英文名称: (4S,5S)-5,8-dimethyl-4-hydroxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione
• 英文别名: (5S,6S)-6-hydroxy-2,5-dimethyl-5,6-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
• CAS: 204331-76-0
• 化学式: C₈H₁₁N₃O₃
• 分子量: 197.194
• InChiKey: BXGLRNBDXFWSLF-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5,8-dimethyl-4-hydroxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione 在 四氧化锇 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 34.0h， 生成 (5S,6R,7R,8R)-6-(tert-Butyl-dimethyl-silanyloxy)-7,8-dihydroxy-2,5-dimethyl-tetrahydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
  参考文献：
  名称：

  Asymmetric synthesis of (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine: a formal synthesis of 1-azagulofagomine analogues

  摘要：

  The stereoselective synthesis of (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine from [(S)R]-(1E,3E)-1-p-tolylsulfinyl-1,3-pentadiene is reported. The domino reaction of the 1-sulfinyldiene with 1,2,4-triazoline-3,5-dione (a hetero Diels-Alder, sulfoxide-sulfenate rearrangement, and sulfenate hydrolysis), eis-dihydroxylation of the resulting alkene and hydrazinolysis with elimination of a N-methylurazol residue are the key steps of the sequence. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.037
• 作为产物：
  描述：

  在 三甲氧基磷 作用下， 生成 (4S,5S)-5,8-dimethyl-4-hydroxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione
  参考文献：
  名称：

  Short enantioselective approach to substituted triazolopyridazines from [(S)R]-1-(1E, 3E)-1-p-tolylsulfinyl-1,3-pentadiene

  摘要：

  Enantiomerically pure hydroxy substituted triazolopyridazine 5a was obtained in one pot under mild conditions by reaction of (+)-(R)-(1E,3E)-1-(p-tolylsulfinyl)-1,3-pentadiene and 4-methyl-1,2,4-triazoline-3,5-dione in the presence of P(OMe)(3). The process involved a tandem Diels-Alder cycloaddition/sulfoxide-sulfenate rearrangement and trapping of the intermediate sulfenate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10776-6