2'-deoxy-N⁶-(naphthalen-1-ylmethy)adenosine | 292862-90-9

• 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: 2'-deoxy-N⁶-(naphthalen-1-ylmethy)adenosine
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-[6-(naphthalen-1-ylmethylamino)purin-9-yl]oxolan-3-ol
• CAS: 292862-90-9
• 化学式: C₂₁H₂₁N₅O₃
• 分子量: 391.429
• InChiKey: QYIINNFPQOVCHD-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-deoxy-N⁶-(naphthalen-1-ylmethy)adenosine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2'-deoxy-5-O-(4,4'-dimethoxytrityl)-N⁶-(naphthalen-1-ylmethy)adenosine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  1H-苯并三唑作为合成辅助剂在 N6-(芳甲基)-2'-脱氧腺苷的简便途径中：插入三向连接的 DNA 嵌入剂

  摘要：

  The 2'-deoxy-N-6-(naphthalen-1-ylmethyl)-(5a) and N-6-(pyren-1-ylntethyl)adenosine (5b) were synthesized in two steps from 2'-deoxyadenosine and the adequate arenecarbaldehyde with 1H-benzotriazole as a synthetic auxiliary (Scheme). When the N-6-(arylmethyl)-2'-deoxyadenosines were inserted into the junction region of a DNA three-way junction, its thermal stability increased.

  DOI：

  10.1002/1522-2675(20000705)83:7<1408::aid-hlca1408>3.0.co;2-u
• 作为产物：
  描述：

  2'-脱氧腺苷 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.0h， 生成 2'-deoxy-N⁶-(naphthalen-1-ylmethy)adenosine
  参考文献：
  名称：

  1H-苯并三唑作为合成辅助剂在 N6-(芳甲基)-2'-脱氧腺苷的简便途径中：插入三向连接的 DNA 嵌入剂

  摘要：

  The 2'-deoxy-N-6-(naphthalen-1-ylmethyl)-(5a) and N-6-(pyren-1-ylntethyl)adenosine (5b) were synthesized in two steps from 2'-deoxyadenosine and the adequate arenecarbaldehyde with 1H-benzotriazole as a synthetic auxiliary (Scheme). When the N-6-(arylmethyl)-2'-deoxyadenosines were inserted into the junction region of a DNA three-way junction, its thermal stability increased.

  DOI：

  10.1002/1522-2675(20000705)83:7<1408::aid-hlca1408>3.0.co;2-u

文献信息

• 1H-Benzotriazole as Synthetic Auxiliary in a Facile Route to N6-(Arylmethyl)-2′-deoxyadenosines: DNA Intercalators Inserted into Three-Way Junctions
  作者：Sherif A. El-Kafrawy、Magdy A. Zahran、Erik B. Pedersen、Claus Nielsen

  DOI：10.1002/1522-2675(20000705)83:7<1408::aid-hlca1408>3.0.co;2-u

  日期：2000.7.5

  The 2'-deoxy-N-6-(naphthalen-1-ylmethyl)-(5a) and N-6-(pyren-1-ylntethyl)adenosine (5b) were synthesized in two steps from 2'-deoxyadenosine and the adequate arenecarbaldehyde with 1H-benzotriazole as a synthetic auxiliary (Scheme). When the N-6-(arylmethyl)-2'-deoxyadenosines were inserted into the junction region of a DNA three-way junction, its thermal stability increased.