N⁶-(3-methylbut-2-enyl)[2-3H]adenosine | 282107-00-0

• 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: N⁶-(3-methylbut-2-enyl)[2-3H]adenosine
• 英文别名: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylimino)-2-tritio-3H-purin-9-yl]oxolane-3,4-diol
• CAS: 282107-00-0
• 化学式: C₁₅H₂₁N₅O₄
• 分子量: 337.355
• InChiKey: USVMJSALORZVDV-JDAKZDBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁶-(3-methylbut-2-enyl)[2-3H]adenosine 在 三氟乙酸 作用下， 生成 N⁶-(3-methylbut-2-enyl)[2-3H]adenine
  参考文献：
  名称：

  N6-alkyladenosines and adenines labelled with tritium

  摘要：

  Catalytic dehalogenation of 2-chloroadenosine with tritium gas led to tritium labelled adenosine which was subsequently alkylated with (E)-4-t-butoxy-3-methylbut-2-enyl bromide or with 3-methylbut-2-enyl bromide to yield labelled (E)-N-6-(4-t-butoxy-3-methylbut-2-enyl)adenosine (<(2a)under bar>) and N-6-(3-methylbut-2-enyl)adenosine (<(2b)under bar>). Acidic hydrolysis of 2b gave N6-(3-methylbut-2-enyl)adenine while acidolysis of 2a with trifluoroacetic acid led to a mixture of (E)-zeatin riboside and (E)-zeatin. Hydrogenation of (Z/E)-zeatin riboside (H-3(2), PdO/BaSO4) afforded labelled dihydrozeatin riboside and, after hydrolysis, dihydrozeatin.

  DOI：

  10.1002/(sici)1099-1344(200004)43:5<523::aid-jlcr339>3.0.co;2-o
• 作为产物：
  描述：

  2-氯腺嘌呤核苷 在 Pd-BaSO₄ 氢氧化钾 、 超重氢 、 3 A molecular sieve 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 N⁶-(3-methylbut-2-enyl)[2-3H]adenosine
  参考文献：
  名称：

  N6-alkyladenosines and adenines labelled with tritium

  摘要：

  Catalytic dehalogenation of 2-chloroadenosine with tritium gas led to tritium labelled adenosine which was subsequently alkylated with (E)-4-t-butoxy-3-methylbut-2-enyl bromide or with 3-methylbut-2-enyl bromide to yield labelled (E)-N-6-(4-t-butoxy-3-methylbut-2-enyl)adenosine (<(2a)under bar>) and N-6-(3-methylbut-2-enyl)adenosine (<(2b)under bar>). Acidic hydrolysis of 2b gave N6-(3-methylbut-2-enyl)adenine while acidolysis of 2a with trifluoroacetic acid led to a mixture of (E)-zeatin riboside and (E)-zeatin. Hydrogenation of (Z/E)-zeatin riboside (H-3(2), PdO/BaSO4) afforded labelled dihydrozeatin riboside and, after hydrolysis, dihydrozeatin.

  DOI：

  10.1002/(sici)1099-1344(200004)43:5<523::aid-jlcr339>3.0.co;2-o

文献信息

• N6-alkyladenosines and adenines labelled with tritium
  作者：Jan Hanu?、V?ra Siglerov�、Miroslav Matucha

  DOI：10.1002/(sici)1099-1344(200004)43:5<523::aid-jlcr339>3.0.co;2-o

  日期：2000.4

  Catalytic dehalogenation of 2-chloroadenosine with tritium gas led to tritium labelled adenosine which was subsequently alkylated with (E)-4-t-butoxy-3-methylbut-2-enyl bromide or with 3-methylbut-2-enyl bromide to yield labelled (E)-N-6-(4-t-butoxy-3-methylbut-2-enyl)adenosine (<(2a)under bar>) and N-6-(3-methylbut-2-enyl)adenosine (<(2b)under bar>). Acidic hydrolysis of 2b gave N6-(3-methylbut-2-enyl)adenine while acidolysis of 2a with trifluoroacetic acid led to a mixture of (E)-zeatin riboside and (E)-zeatin. Hydrogenation of (Z/E)-zeatin riboside (H-3(2), PdO/BaSO4) afforded labelled dihydrozeatin riboside and, after hydrolysis, dihydrozeatin.