3-chloro-5-iodo-2-methoxybenzoic acid | 350236-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-5-iodo-2-methoxybenzoic acid
• CAS: 350236-34-9
• 化学式: C₈H₆ClIO₃
• 分子量: 312.491
• InChiKey: GIRUDVVCUMEHRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-己炔酸甲酯 、 sodium methylate 、 蛋白银染试剂盒 、 3-chloro-5-iodo-2-methoxybenzoic acid 以79.0 mg的产率得到3-Chloro-2-methoxy-5-[(Z)-5-methoxycarbonyl-1-(4-methoxy-3-methoxycarbonyl-phenyl)-pent-1-enyl]-benzoic acid methyl ester
  参考文献：
  名称：

  Solid-Phase Synthesis of the Alkenyldiarylmethane (ADAM) Series of Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  The Sonogashira and Stille cross-coupling reactions have been employed in the synthesis of several non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the alkenyldiarylmethane (ADAM) series. The synthesis has been carried out both in solution and on a solid support. In contrast to previous syntheses of NNRTIs in the ADAM series, the present strategy allows the incorporation of differently substituted aromatic rings in a stereochemically defined fashion. The most potent of the new ADAMs inhibited the cytopathic effect of HIV-1(RF) in CEM-SS cell culture with an EC50 value of 20 nM.

  DOI：

  10.1021/jo0100291
• 作为产物：
  描述：

  methyl 3-chloro-5-iodo-2-methoxybenzoate 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到3-chloro-5-iodo-2-methoxybenzoic acid
  参考文献：
  名称：

  Solid-Phase Synthesis of the Alkenyldiarylmethane (ADAM) Series of Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  The Sonogashira and Stille cross-coupling reactions have been employed in the synthesis of several non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the alkenyldiarylmethane (ADAM) series. The synthesis has been carried out both in solution and on a solid support. In contrast to previous syntheses of NNRTIs in the ADAM series, the present strategy allows the incorporation of differently substituted aromatic rings in a stereochemically defined fashion. The most potent of the new ADAMs inhibited the cytopathic effect of HIV-1(RF) in CEM-SS cell culture with an EC50 value of 20 nM.

  DOI：

  10.1021/jo0100291