(4S,5S)-5,8-dimethyl-4-tert-butyldimethylsilyloxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione | 690995-59-6

• 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-tert-butyldimethylsilyloxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione
• 英文别名: (5S,6S)-6-[tert-butyl(dimethyl)silyl]oxy-2,5-dimethyl-5,6-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
• CAS: 690995-59-6
• 化学式: C₁₄H₂₅N₃O₃Si
• 分子量: 311.456
• InChiKey: CPZBUTMWLAWCGT-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5,8-dimethyl-4-tert-butyldimethylsilyloxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione 在 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 44.0h， 生成 (2S,3S,4R,5S)-5,8-dimethyl-2,3-O-isopropylidene-4-tert-butyldimethylsilyloxy-1,6,8-triazobicyclo[4,3,0]nonan-7,9-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：

  叔丁基二甲硅基三氟甲磺酸酯 、 (4S,5S)-5,8-dimethyl-4-hydroxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以57%的产率得到(4S,5S)-5,8-dimethyl-4-tert-butyldimethylsilyloxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-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

文献信息

• Asymmetric synthesis of (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine: a formal synthesis of 1-azagulofagomine analogues
  作者：Y. Arroyo、J.F. Rodrı́guez、M. Santos、M.A. Sanz Tejedor、I. Vaca、J.L. Garcı́a Ruano

  DOI：10.1016/j.tetasy.2004.01.037

  日期：2004.3

  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.