(3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine | 28941-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine
• 英文别名: L-Xylo-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazin；(4R,5R,6S)-6-methyl-1,4,5,6-tetrahydropyridazine-4,5-diol
• CAS: 28941-20-0
• 化学式: C₅H₁₀N₂O₂
• 分子量: 130.147
• InChiKey: OYLDNGRPKQPFAY-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine 生成 1.4-Bis-acetamino-2,3-di-O-acetyl-1,4,5-tridesoxy-L-xylit
  参考文献：
  名称：

  Paulsen,H.; Steinert,G., Chemische Berichte, 1970, vol. 103, p. 1834 - 1845

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S,5S)-5,8-dimethyl-4-hydroxy-1,6,8-triazobicyclo[4,3,0]non-2-ene-7,9-dione 在 Oxone 、 1,1,1-三氟丙酮 、 碳酸氢钠 、 对甲苯磺酸 、 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 33.0h， 生成 (3S,4R,5R)-4,5-dihydroxy-3-methyl-2,3,4,5-tetrahydropyridazine
  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

• Paulsen,H.; Steinert,G., Chemische Berichte, 1970, vol. 103, p. 1834 - 1845
  作者：Paulsen,H.、Steinert,G.

  DOI：——

  日期：——
• 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.