N-[2-(3-methylphenyl)ethoxy]phthalimide | 191473-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-[2-(3-methylphenyl)ethoxy]phthalimide
• 英文别名: 2-[2-(3-Methylphenyl)ethoxy]isoindole-1,3-dione
• CAS: 191473-35-5
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: YVIWJQFUBKPJJH-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±48.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(3-methylphenyl)ethoxy]phthalimide 在 一水合肼 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 [2-(3-methylphenyl)ethoxy]amine
  参考文献：
  名称：

  钯(II)催化芳烃的远程元C-H功能化，通过多任务草酰胺作为连接剂实现

  摘要：

  已经建立了使用腈模板作为导向基团在含有草酰胺的芳烃中进行间位-C-H键的钯催化烯化反应。该方法表现出高间位选择性并耐受不同的官能团，例如苄氧基酰胺和烯烃底物。以良好的收率获得了所需的产物。这种方法能够对天然产物和药物进行修饰，并且也适用于克级。此外，通过选择性裂解酰胺键或O-N键，可以轻松去除定向模板，以获得间位官能化的羟胺和苯甲醇。所提出的方法对于新药的设计具有巨大的潜力。

  DOI：

  10.1021/acs.orglett.3c01101
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 3-甲基苯乙醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以96%的产率得到N-[2-(3-methylphenyl)ethoxy]phthalimide
  参考文献：
  名称：

  Synthesis and Anti-HIV-1 Activity of a Series of 1-Alkoxy-5-alkyl-6-(arylthio)uracils

  摘要：

  A series of 1-alkoxy-5-alkyl-6-(arylthio)uracils was synthesized and tested for their ability to inhibit HIV-1 replication. Treatment of 2-alkyl-3,3-bis(methylthio)acryloyl chlorides (5a-e) with AgOCN in benzene followed by reaction of the resulting isocyanates 6a-e with an appropriate alkoxyamine gave N-alkoxy-N'-((2-alkyl-3,3-bis(methylthio (10a-z) in good to excellent yields. Cyclization of 10a-z in AcOH containing st catalytic amount of p-TsOH produced 1-alkaxy-5-alkyl-6-(methylthio)uracils (11a-z). Oxidation of 11a-z with 3-chloroperoxybenzoic acid in CH2Cl2 resulted in high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils (12a-x and 12z) and 1-(benzyloxy)-6-(methylsulfinyl)thymine (12y), which were subsequently reacted with an appropriate arenethiol in ethanolic NaOH solution to afford 1-alkoxy-5-alkyl-6-(arylthio)uracils (14-49). Substitution at the 3- and 5-positions of the C-6-(phenylthio) ring by two methyl groups significantly increased its original anti-HIV-l activity (EC50: 6-((3,5-dimethylphenyl)thio)-5-isopropyl-1-propoxyuracil (18), 0.064 mu M; 6-((3,5-dimethylphenyl)thio)-1-(3-hydroxypropoxy)-5-isopropyluracil (23), 0.19 mu M). Among the various alkoxy substituents at the N-1, the propoxy group was the most beneficial for improving the anti-HIV-1 activity. The 1-propoxy derivative 18 proved to be the most potent inhibitor of HIV-1 replication, followed by the 1-(3-hydroxypropoxy) derivative 23. Introduction of an isopropyl group at C-5 of the uracil base also remarkably enhanced the activity. When compound 18 was incubated with a rat liver homogenate preparation, no metabolite was observed, thus confirming the metabolic stability of the N-O bond in these 1-alkoxyuracils.

  DOI：

  10.1021/jm9607921

文献信息

• Synthesis and Anti-HIV-1 Activity of a Series of 1-Alkoxy-5-alkyl-6-(arylthio)uracils
  作者：Dae-Kee Kim、Jongsik Gam、Young-Woo Kim、Jinsoo Lim、Hun-Taek Kim、Key H. Kim

  DOI：10.1021/jm9607921

  日期：1997.7.1

  A series of 1-alkoxy-5-alkyl-6-(arylthio)uracils was synthesized and tested for their ability to inhibit HIV-1 replication. Treatment of 2-alkyl-3,3-bis(methylthio)acryloyl chlorides (5a-e) with AgOCN in benzene followed by reaction of the resulting isocyanates 6a-e with an appropriate alkoxyamine gave N-alkoxy-N'-((2-alkyl-3,3-bis(methylthio (10a-z) in good to excellent yields. Cyclization of 10a-z in AcOH containing st catalytic amount of p-TsOH produced 1-alkaxy-5-alkyl-6-(methylthio)uracils (11a-z). Oxidation of 11a-z with 3-chloroperoxybenzoic acid in CH2Cl2 resulted in high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils (12a-x and 12z) and 1-(benzyloxy)-6-(methylsulfinyl)thymine (12y), which were subsequently reacted with an appropriate arenethiol in ethanolic NaOH solution to afford 1-alkoxy-5-alkyl-6-(arylthio)uracils (14-49). Substitution at the 3- and 5-positions of the C-6-(phenylthio) ring by two methyl groups significantly increased its original anti-HIV-l activity (EC50: 6-((3,5-dimethylphenyl)thio)-5-isopropyl-1-propoxyuracil (18), 0.064 mu M; 6-((3,5-dimethylphenyl)thio)-1-(3-hydroxypropoxy)-5-isopropyluracil (23), 0.19 mu M). Among the various alkoxy substituents at the N-1, the propoxy group was the most beneficial for improving the anti-HIV-1 activity. The 1-propoxy derivative 18 proved to be the most potent inhibitor of HIV-1 replication, followed by the 1-(3-hydroxypropoxy) derivative 23. Introduction of an isopropyl group at C-5 of the uracil base also remarkably enhanced the activity. When compound 18 was incubated with a rat liver homogenate preparation, no metabolite was observed, thus confirming the metabolic stability of the N-O bond in these 1-alkoxyuracils.
• Palladium(II)-Catalyzed Remote <i>meta</i>-C–H Functionalization of Arenes Enabled by Multitasking Oxyamides as the Linker
  作者：Yue-Lu Zhu、Qiu-Xue Sun、Jin-Shuo Feng、You-Dong Shao、Jiao Chen

  DOI：10.1021/acs.orglett.3c01101

  日期：2023.6.23

  A palladium-catalyzed olefination of meta-C–H bonds in arenes containing oxyamides using a nitrile template as the directing group has been established. The methodology exhibited high meta-selectivity and tolerated different functional groups such as benzyloxyamides and olefin substrates. The desired products were obtained in good yields. This approach enabled the modification of natural products and

  已经建立了使用腈模板作为导向基团在含有草酰胺的芳烃中进行间位-C-H键的钯催化烯化反应。该方法表现出高间位选择性并耐受不同的官能团，例如苄氧基酰胺和烯烃底物。以良好的收率获得了所需的产物。这种方法能够对天然产物和药物进行修饰，并且也适用于克级。此外，通过选择性裂解酰胺键或O-N键，可以轻松去除定向模板，以获得间位官能化的羟胺和苯甲醇。所提出的方法对于新药的设计具有巨大的潜力。