1-(1-β-D-galactopyranosyloxy)phthalazine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-β-D-galactopyranosyloxy)phthalazine
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-phthalazin-1-yloxyoxane-3,4,5-triol
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: YXKFCOVTCNLYMQ-LARJDALCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(2H)-酞嗪酮 在 四氯化锡 三乙胺 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 1-(1-β-D-galactopyranosyloxy)phthalazine
  参考文献：
  名称：

  Synthesis and structural characterization of 1-(d-glycosyloxy)phthalazines

  摘要：

  Coupling of the trimethylsilyl derivative of (2H)phthalazin-1-one with 1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranose and 1,2,3,4,6-penta-O-acetyl-alpha-D-galactopyranose in the presence of stannic chloride gave the respective glycosides, 2-(per-O-acetyl-D-glycosyloxy)phthalazines, which upon deacetylation gave the respective unprotected analogues. Under the same conditions 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose gave 1-(2,3,5-tri-O-acetyl-alpha-D-ribofuranosyloxy)phthalazine. Electrospray mass spectrometry aided the structural characterization of this series of 1-(D-glycosylyloxy)phthalazines. Low energy collisionally-induced dissociation tandem mass spectrometry of the protonated molecules confirmed the MS fragmentation routes and the structural identities of this novel series of glycosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.016

文献信息

• Synthesis and structural characterization of 1-(d-glycosyloxy)phthalazines
  作者：Abdellfattah Z Haikal、El Sayed H El Ashry、Joseph Banoub

  DOI：10.1016/j.carres.2003.08.016

  日期：2003.10

  Coupling of the trimethylsilyl derivative of (2H)phthalazin-1-one with 1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranose and 1,2,3,4,6-penta-O-acetyl-alpha-D-galactopyranose in the presence of stannic chloride gave the respective glycosides, 2-(per-O-acetyl-D-glycosyloxy)phthalazines, which upon deacetylation gave the respective unprotected analogues. Under the same conditions 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose gave 1-(2,3,5-tri-O-acetyl-alpha-D-ribofuranosyloxy)phthalazine. Electrospray mass spectrometry aided the structural characterization of this series of 1-(D-glycosylyloxy)phthalazines. Low energy collisionally-induced dissociation tandem mass spectrometry of the protonated molecules confirmed the MS fragmentation routes and the structural identities of this novel series of glycosides. (C) 2003 Elsevier Ltd. All rights reserved.