2-羟基嘌呤 | 2308-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-羟基嘌呤
• 中文别名: 1,3-二氢-2H-嘌呤-2-酮
• 英文名称: 2-Hydroxypurine
• 英文别名: 2-Hydroxypurin；3,7-dihydropurin-2-one
• CAS: 2308-57-8
• 化学式: C₅H₄N₄O
• mdl: MFCD00055969
• 分子量: 136.113
• InChiKey: CRIZPXKICGBNKG-UHFFFAOYSA-N

物化性质

• 密度：
  1.89±0.1 g/cm3(Predicted)
• 溶解度：
  0.02 M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-羟基嘌呤 在 magnesium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 1,9-Dihydro-1,9-bis[(tert-butyldimethylsilyloxy)methyl]-6-[2-(phenyl)ethyl]-2H-purin-2-one
  参考文献：
  名称：

  Synthesis of 6-substituted purin-2-ones with potential cytokinin activity

  摘要：

  通过将格氏试剂完全区域选择性地加成到 N-保护的嘌呤-2-酮上，然后进行后气化和脱保护，制备出了 6-取代的嘌呤-2-酮。目标化合物可被视为强效细胞分裂素反式玉米素和苄基氨基嘌呤（BAP）的类似物，而且大多数 BAP 类似物都能诱导萝卜子叶重量增长。受 N 保护的 (E)-6-styrylpurin-2-one 在普通日光下会发生从头到尾的 [2+2] 二聚反应，生成 1α、2α、3β、4β 取代的环丁烷 15。在紫外线照射下，反式化合物异构化为相应的顺式异构体。化合物 15 的结构是在 150 K 温度下通过单晶 X 射线衍射方法确定的。

  DOI：

  10.1039/b101327k

文献信息

• Regiochemistry in addition of Grignard reagents to N,N′-dibenzylated 2-purinones
  作者：Geir Andresen、Lise-Lotte Gundersen、Frode Rise

  DOI：10.1016/0040-4020(96)00779-x

  日期：1996.9

  1,3-, 1,7-, 1,9- and 3,7-dibenzylpurin-2-one form stable adducts when reacted with Grignard reagents. Reaction took place in the purine 6- or 8-position, and substantial differences in the regiochemical outcome of the reactions were found among the isomers. Several new classes of purinones are described here for the first time. The structure elucidations of the products were accomplished by HETCOR

  当与格氏试剂反应时，1,3-，1,7-，1,9-和3,7-二苄基嘌呤-2-酮形成稳定的加合物。反应发生在嘌呤6或8位，异构体之间反应的区域化学结果存在实质性差异。这里首次描述了几种新的嘌呤类。通过HETCOR，COLOC，GA-HMQC和GA-HMBC NMR光谱对产物进行结构阐明。
• Johns, Journal of Biological Chemistry, 1912, vol. 11, p. 77
  作者：Johns

  DOI：——

  日期：——
• Regioselective addition of Grignard reagents to a 2-oxopurinium salt
  作者：Geir Andresen、Lise-Lotte Gundersen、Max Lundmark、Frode Rise、Staffan Sundell

  DOI：10.1016/0040-4020(95)00080-r

  日期：1995.3

  Treatment of 6-ethoxy-1,3,6,7-tetrahydro-1,3,7-tribanzyl-2H-purin-2-one with trimethyl-chlorosilane gave a stable tribenzylated 2-oxopurinium salt, which selectively added Grignard reagents in the 6-position. The structure of the adducts were established from long range HETCOR NMR experiments.
• 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.
• Purine studies. Part I. Stability to acid and alkali. Solubility. Ionization. Comparison with pteridines
  作者：Adrien Albert、D. J. Brown

  DOI：10.1039/jr9540002060

  日期：——

表征谱图