3-methylxanthine | 3080-28-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3-methylxanthine
• 英文别名: 3-Methylxanthosine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methylpurine-2,6-dione
• CAS: 3080-28-2
• 化学式: C₁₁H₁₄N₄O₆
• 分子量: 298.255
• InChiKey: GYVBAVMQKDJAFI-KQYNXXCUSA-N

物化性质

• 熔点：
  200 °C (decomp)
• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-methylxanthine 在 盐酸 作用下， 以 水 为溶剂， 生成 3-甲基黄嘌呤
  参考文献：
  名称：

  Itaya, Taisuke; Harada, Tsunehiro, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 5, p. 1235 - 1238

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-(methylamino)imidazole-4-carboxamide 在 sodium hydroxide 、 sodium acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 3-methylxanthine
  参考文献：
  名称：

  Itaya, Taisuke; Harada, Tsunehiro, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 5, p. 1235 - 1238

  摘要：

  DOI：

文献信息

• High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries
  作者：Brett C. Bookser、Nicholas B. Raffaele

  DOI：10.1021/jo061885l

  日期：2007.1.1

  [GRAPHICS]The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 degrees C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield +/- SD was 26 +/- 16%, and the average purity +/- SD was 95 +/- 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.
• ITAYA, TAISUKE;HARADA, TSUNEHIRO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1235-1238
  作者：ITAYA, TAISUKE、HARADA, TSUNEHIRO

  DOI：——

  日期：——