(6-氨基-7H-嘌呤-8-基)甲醇 | 30466-95-6

• 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: (6-氨基-7H-嘌呤-8-基)甲醇
• 英文名称: 6-Amino-8-hydroxymethylpurin
• 英文别名: 8-Hydroxymethyl-9H-adenin；(6-amino-7(9)H-purin-8-yl)-methanol；(6-amino-7H-purin-8-yl)methanol
• CAS: 30466-95-6
• 化学式: C₆H₇N₅O
• mdl: MFCD00985243
• 分子量: 165.154
• InChiKey: ZPWCPESWVACHTD-UHFFFAOYSA-N

物化性质

• 沸点：
  579.1±40.0 °C(Predicted)
• 密度：
  1.691±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (6-氨基-7H-嘌呤-8-基)甲醇 在 吡啶 作用下， 反应 20.0h， 以61%的产率得到Acetic acid 6-amino-7H-purin-8-ylmethyl ester
  参考文献：
  名称：

  Synthesis of 4,6-diamino-5-(polyhydroxyalkylamido)pyrimidines: conformation of the sugar chain

  摘要：

  Condensation of 4,5,6-triaminopyrimidine with ethyl glycolate, D-ribono-1,4-lactone, D-allono-1,4-lactone, D-glucono-1,5-lactone, and L-gulono-1,4-lactone led to the corresponding 4,6-diamino-5-(hydroxyalkylamido)pyrimidines (1a-e). The conformations in acidic aqueous solution of these acyclic carbohydrate derivatives were determined from the proton-proton NMR coupling constants at 300 MHz. The polyhydroxyalkyl chain of compounds 1b-e adopt sickle conformations in order to avoid the 1,3-parallel interactions between hydroxyl groups present in the planar zigzag conformer. Cyclization of 4,6-diamino-5-(hydroxyacetamido)pyrimidine (1a) afforded 8-(hydroxymethyl)adenine (2a), which was acetylated to give 2f. The C-13 NMR spectra of compounds 1a-e and 2a and f are also reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00078-0
• 作为产物：
  描述：

  N-(4,6-diamino-pyrimidin-5-yl)-2-hydroxy-acetamide 以 neat (no solvent) 为溶剂， 以40%的产率得到(6-氨基-7H-嘌呤-8-基)甲醇
  参考文献：
  名称：

  Synthesis of 4,6-diamino-5-(polyhydroxyalkylamido)pyrimidines: conformation of the sugar chain

  摘要：

  Condensation of 4,5,6-triaminopyrimidine with ethyl glycolate, D-ribono-1,4-lactone, D-allono-1,4-lactone, D-glucono-1,5-lactone, and L-gulono-1,4-lactone led to the corresponding 4,6-diamino-5-(hydroxyalkylamido)pyrimidines (1a-e). The conformations in acidic aqueous solution of these acyclic carbohydrate derivatives were determined from the proton-proton NMR coupling constants at 300 MHz. The polyhydroxyalkyl chain of compounds 1b-e adopt sickle conformations in order to avoid the 1,3-parallel interactions between hydroxyl groups present in the planar zigzag conformer. Cyclization of 4,6-diamino-5-(hydroxyacetamido)pyrimidine (1a) afforded 8-(hydroxymethyl)adenine (2a), which was acetylated to give 2f. The C-13 NMR spectra of compounds 1a-e and 2a and f are also reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00078-0

文献信息

• SCHWARTZ, ALAN W., ADV. SPACE RES., 9,(1989) N, C. 77-81
  作者：SCHWARTZ, ALAN W.

  DOI：——

  日期：——
• SCHWARTZ, ALAN W.;BAKKER, C. G., SCIENCE, 245,(1989) N922, C. 1102
  作者：SCHWARTZ, ALAN W.、BAKKER, C. G.

  DOI：——

  日期：——
• Synthesis of 4,6-diamino-5-(polyhydroxyalkylamido)pyrimidines: conformation of the sugar chain
  作者：Derek Horton、Oscar Varela

  DOI：10.1016/s0008-6215(98)00078-0

  日期：1998.3

  Condensation of 4,5,6-triaminopyrimidine with ethyl glycolate, D-ribono-1,4-lactone, D-allono-1,4-lactone, D-glucono-1,5-lactone, and L-gulono-1,4-lactone led to the corresponding 4,6-diamino-5-(hydroxyalkylamido)pyrimidines (1a-e). The conformations in acidic aqueous solution of these acyclic carbohydrate derivatives were determined from the proton-proton NMR coupling constants at 300 MHz. The polyhydroxyalkyl chain of compounds 1b-e adopt sickle conformations in order to avoid the 1,3-parallel interactions between hydroxyl groups present in the planar zigzag conformer. Cyclization of 4,6-diamino-5-(hydroxyacetamido)pyrimidine (1a) afforded 8-(hydroxymethyl)adenine (2a), which was acetylated to give 2f. The C-13 NMR spectra of compounds 1a-e and 2a and f are also reported. (C) 1998 Elsevier Science Ltd. All rights reserved.