(4-azido-3-iodophenyl)-butyric anhydride | 161084-84-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4-azido-3-iodophenyl)-butyric anhydride
• 英文别名: 4-(4-Azido-3-iodophenyl)butanoyl 4-(4-azido-3-iodophenyl)butanoate
• CAS: 161084-84-0
• 化学式: C₂₀H₁₈I₂N₆O₃
• 分子量: 644.21
• InChiKey: HLXCNJSVPCFQLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-二脱氧腺苷 、 (4-azido-3-iodophenyl)-butyric anhydride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 120.0h， 以90%的产率得到3'-<(4-azido-3-iodophenyl)-butyryl>-2',5'-dideoxyadenosine
  参考文献：
  名称：

  Synthesis of Iodo-aryl-azido Adenosine Analogs as Affinity Ligands for Adenylyl Cyclase

  摘要：

  Potential affinity probes for adenylyl cyclase were synthesized that take advantage of the enzyme's sensitivity to ''P''-site-mediated inhibition by 2',5'-dideoxyadenosine analogs and its tolerance for large 3'-ribose substitutions. We report the synthesis of a series of 3'-substituted 2',5'-dideoxyadenosine analogs. The syntheses involved the intermediate formation of symmetric anhydrides that were then coupled to 2',5'-dideoxyadenosine by base-catalyzed esterification at the 3'-ribose position.

  DOI：

  10.1080/15257779408010676
• 作为产物：
  描述：

  (4-azido-3-iodophenyl)-butyric acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4-azido-3-iodophenyl)-butyric anhydride
  参考文献：
  名称：

  Synthesis of Iodo-aryl-azido Adenosine Analogs as Affinity Ligands for Adenylyl Cyclase

  摘要：

  Potential affinity probes for adenylyl cyclase were synthesized that take advantage of the enzyme's sensitivity to ''P''-site-mediated inhibition by 2',5'-dideoxyadenosine analogs and its tolerance for large 3'-ribose substitutions. We report the synthesis of a series of 3'-substituted 2',5'-dideoxyadenosine analogs. The syntheses involved the intermediate formation of symmetric anhydrides that were then coupled to 2',5'-dideoxyadenosine by base-catalyzed esterification at the 3'-ribose position.

  DOI：

  10.1080/15257779408010676