2-氯-1,4-二-n-丙氧基苯 | 916791-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-氯-1,4-二-n-丙氧基苯
• 中文别名: 1-氯-2,5-二-N-丙氧基苯
• 英文名称: 2-chloro-1,4-dipropoxybenzene
• 英文别名: 1-chloro-2,5-dipropoxybenzene
• CAS: 916791-98-5
• 化学式: C₁₂H₁₇ClO₂
• mdl: MFCD00048688
• 分子量: 228.719
• InChiKey: SWQFWWUXVCCQSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  306.6±22.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  2-氯-1,4-二-n-丙氧基苯 在 HNO₃-SiO₂ 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 1-(4-chloro-2,5-dipropoxyphenyl)-3-(3-propoxypropyl)thiourea
  参考文献：
  名称：

  Structure–activity relationship studies of 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, a non-nucleoside reverse transcriptase inhibitor of human immunodeficiency virus type-1

  摘要：

  The reverse transcriptase (RT) of the human immunodeficiency virus type-1 (HIV-1) is still a prime target for drug development due to the continuing need to block drug-resistant RT mutants by new inhibitors. We have previously identified 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, compound 1, as a potent RI inhibitor from an available chemical library. Here, we further modified this compound to study structure activity relationships when replacing various groups in the molecule. Different functional groups were systematically introduced on the aromatic ring and the aliphatic chain of the compound was modified. The effect of these modifications on viral infectivity was then evaluated. The most potent compound found was propyl 4-(amino-N-(4-chloro-2,5-dimethoxyphenyl)methanethioamino)butanoate, 45c, which inhibited infectivity with a calculated IC50 of about 1.1 mu M. Docking studies identified potential important interactions between the top scoring ligands and HIV-1 RT, and the predicted relative affinity of the ligands was found to be in agreement with the experimental results. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.003
• 作为产物：
  描述：

  1-碘代丙烷 、 氯氢醌 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以87%的产率得到2-氯-1,4-二-n-丙氧基苯
  参考文献：
  名称：

  Structure–activity relationship studies of 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, a non-nucleoside reverse transcriptase inhibitor of human immunodeficiency virus type-1

  摘要：

  The reverse transcriptase (RT) of the human immunodeficiency virus type-1 (HIV-1) is still a prime target for drug development due to the continuing need to block drug-resistant RT mutants by new inhibitors. We have previously identified 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, compound 1, as a potent RI inhibitor from an available chemical library. Here, we further modified this compound to study structure activity relationships when replacing various groups in the molecule. Different functional groups were systematically introduced on the aromatic ring and the aliphatic chain of the compound was modified. The effect of these modifications on viral infectivity was then evaluated. The most potent compound found was propyl 4-(amino-N-(4-chloro-2,5-dimethoxyphenyl)methanethioamino)butanoate, 45c, which inhibited infectivity with a calculated IC50 of about 1.1 mu M. Docking studies identified potential important interactions between the top scoring ligands and HIV-1 RT, and the predicted relative affinity of the ligands was found to be in agreement with the experimental results. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.003

文献信息

• METHOD FOR PRODUCING BIARYL COMPOUND
  申请人：Sato Koichi

  公开号：US20100087680A1

  公开（公告）日：2010-04-08

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种制备双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱的存在下，将芳香有机化合物与选自芳香基有机硼化合物和硼氧化物化合物组的至少一种化合物反应。
• PROCESS FOR PRODUCING BIARYL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1914221A1

  公开（公告）日：2008-04-23

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种生产双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱存在下，使芳香族有机化合物与至少一种选自由芳香族有机硼化合物和硼氧化合物组成的组中的化合物反应。
• Structure–activity relationship studies of 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, a non-nucleoside reverse transcriptase inhibitor of human immunodeficiency virus type-1
  作者：Michal Weitman、Keti Lerman、Abraham Nudelman、Dan Thomas Major、Amnon Hizi、Alon Herschhorn

  DOI：10.1016/j.ejmech.2010.11.003

  日期：2011.2

  The reverse transcriptase (RT) of the human immunodeficiency virus type-1 (HIV-1) is still a prime target for drug development due to the continuing need to block drug-resistant RT mutants by new inhibitors. We have previously identified 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, compound 1, as a potent RI inhibitor from an available chemical library. Here, we further modified this compound to study structure activity relationships when replacing various groups in the molecule. Different functional groups were systematically introduced on the aromatic ring and the aliphatic chain of the compound was modified. The effect of these modifications on viral infectivity was then evaluated. The most potent compound found was propyl 4-(amino-N-(4-chloro-2,5-dimethoxyphenyl)methanethioamino)butanoate, 45c, which inhibited infectivity with a calculated IC50 of about 1.1 mu M. Docking studies identified potential important interactions between the top scoring ligands and HIV-1 RT, and the predicted relative affinity of the ligands was found to be in agreement with the experimental results. (C) 2010 Elsevier Masson SAS. All rights reserved.