(E)-4-t-butoxy-3-methylbut-2-enyl bromide | 282106-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-t-butoxy-3-methylbut-2-enyl bromide
• 英文别名: 4-t-Butoxy-3-methyl-trans-but-2-enylbromide；(E)-4-bromo-2-methyl-1-[(2-methylpropan-2-yl)oxy]but-2-ene
• CAS: 282106-98-3
• 化学式: C₉H₁₇BrO
• 分子量: 221.137
• InChiKey: IBEFZZJUQBQAQW-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-t-butoxy-3-methylbut-2-enyl bromide 在 3 A molecular sieve 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[(E)-4-hydroxy-3-methylbut-2-enyl]imino-2-tritio-3H-purin-9-yl]oxolane-3,4-diol
  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：

  叔丁醇 、 天然橡胶 在 tert-butyl hypobromite 作用下， 反应 4.0h， 生成 (E)-4-t-butoxy-3-methylbut-2-enyl bromide
  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.