N-(2-甲氧基苯基)吡啶-3-胺 | 1028223-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-(2-甲氧基苯基)吡啶-3-胺
• 英文名称: N-(3-pyridyl)-o-anisidine
• 英文别名: N-methyl-N-phenylpyridin-3-amine；N-(2-methoxyphenyl)pyridin-3-amine；N-(2-Methoxyphenyl)pyridin-3-amine
• CAS: 1028223-83-7
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: DJZOPDXEAZIAOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  340.6±22.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-(iodopentyl) cyclohexane 、 N-(2-甲氧基苯基)吡啶-3-胺 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 生成 N-(5-cyclohexylpentyl)-N-(2-methoxyphenyl)pyridin-3-amine
  参考文献：
  名称：

  Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens

  摘要：

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.10.065
• 作为产物：
  描述：

  3-氯吡啶 、 邻甲氧基苯胺 在 dicyclohexyl-[2-(2,6-dimethoxyphenyl)-3H-inden-1-yl]phosphane 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以49%的产率得到N-(2-甲氧基苯基)吡啶-3-胺
  参考文献：
  名称：

  在无溶剂和含水条件下，芳基氯化物和杂芳基氯化物在布赫瓦尔德-哈特维格交叉偶联反应中应用2-芳基茚基膦配体

  摘要：

  使用Pd（dba）2 /配体1催化系统开发了一种有效的无溶剂方案，用于芳基和杂芳基氯化物与伯胺和仲胺的布赫瓦尔德-哈特维格交叉偶联反应。值得注意的是，催化体系还可以在水性条件下有效地催化反应。

  DOI：

  10.1039/c7ob01199g

文献信息

• Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure–Activity Relationships
  作者：Qilong Shen、Tokutaro Ogata、John F. Hartwig

  DOI：10.1021/ja077074w

  日期：2008.5.1

  chelating alkylphosphines for the amination of heteroaryl and aryl chlorides, bromides, and iodides. In the presence of this catalyst, aryl and heteroaryl chlorides, bromides, and iodides react with many primary amines in high yields with part-per-million quantities of palladium precursor and ligand. Many reactions of primary amines with both heteroaryl and aryl chlorides, bromides, and iodides occur to

  我们描述了对一类高效和选择性催化剂的配体结构和活性之间的范围和关系的系统研究，该催化剂包含空间位阻螯合烷基膦，用于杂芳基和芳基氯化物、溴化物和碘化物的胺化。在这种催化剂的存在下，芳基和杂芳基氯化物、溴化物和碘化物与许多伯胺以高产率反应，并产生百万分之几的钯前体和配体。伯胺与杂芳基和芳基氯化物、溴化物和碘化物的许多反应在 0.0005-0.05 mol% 的催化剂下完成。将这种催化剂在这些负载下与伯胺偶联的反应性与由受阻单膦和卡宾生成的催化剂进行比较，这些数据说明了螯合的好处。对活性最高的催化剂结构变体的研究表明，双齿结构中的刚性主链、强电子供体和严重的阻碍都有助于其高反应性。因此，这些配合物构成了芳基卤化物胺化的第四代催化剂，其活性与基于单膦和卡宾的催化剂相辅相成。
• Carbene adduct of cyclopalladated ferrocenylimine-assisted synthesis of aminopyridine derivatives by the amination of chloropyridines with primary and secondary amines
  作者：Bing Mu、Jingya Li、Yangjie Wu

  DOI：10.1002/aoc.3026

  日期：2013.9

  on Buchwald–Hartwig aminations. Using 1 mol% N‐heterocyclic carbene adduct of cyclopalladated ferrocenylimine in the presence of 1.5 equiv. tBuOK as base in dioxane at 110°C offered moderate to excellent yields in the reaction of chloropyridines with primary and secondary amines, including sterically hindered amines and alkyl amines.

  基于布赫瓦尔德-哈特维格胺的胺化反应，提出了一种高效，简单的合成氨基吡啶衍生物的方法。在1.5当量的情况下，使用1 mol％的N-杂环卡宾环合钯的二茂铁亚胺加成物。吨丁醇钾作为在110℃下基在二恶烷中的氯吡啶与伯和仲胺反应提供中度至良好的产率，包括空间位阻胺和烷基胺。
• Solvent-Free Buchwald–Hartwig Amination of Heteroaryl Chlorides by <i>N</i>-Heterocyclic Carbene–Palladium Complex (SIPr)^Ph2Pd(cin)Cl at Room Temperature
  作者：Jia-Sheng Ouyang、Xinhuan Zhang、Bendu Pan、Haobin Zou、Albert S. C. Chan、Liqin Qiu

  DOI：10.1021/acs.orglett.3c02651

  日期：2023.10.20

  Using the robust N-heterocyclic carbene–palladium complex (SIPr)Ph2Pd(cin)Cl, a highly efficient and easy-to-operate method has been developed at room temperature for the solvent-free Buchwald–Hartwig amination of heteroaryl chlorides with various amines. The amount of catalyst can be as low as 0.05 wt %. The system was demonstrated on 47 substrates and successfully applied to the synthesis of commercial

  使用稳健的N -杂环卡宾-钯配合物 (SIPr) Ph2 Pd(cin)Cl，在室温下开发了一种高效且易于操作的方法，用于杂芳基氯与各种化合物的无溶剂 Buchwald-Hartwig 胺化胺类。催化剂的量可以低至0.05wt%。该系统在47种底物上进行了验证，并成功应用于商业药物和候选药物的高产率合成。此外，该方案可用于制备多克规模的苯胺衍生物，而不会损失产量。
• Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens
  作者：Tryphon K. Mazu、Jagan R. Etukala、Xue Y. Zhu、Melissa R. Jacob、Shabana I. Khan、Larry A. Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2010.10.065

  日期：2011.1

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.
• Application of a 2-aryl indenylphosphine ligand in the Buchwald–Hartwig cross-coupling reactions of aryl and heteroaryl chlorides under the solvent-free and aqueous conditions
  作者：Yan Liu、Jia Yuan、Zi-Fei Wang、Si-Hao Zeng、Meng-Yue Gao、Mei-Lin Ruan、Jian Chen、Guang-Ao Yu

  DOI：10.1039/c7ob01199g

  日期：——

  An efficient solvent-free protocol for the Buchwald–Hartwig cross-coupling reaction of aryl and heteroaryl chlorides with primary and secondary amines using the Pd(dba)2/ligand 1 catalytic system has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.

  使用Pd（dba）2 /配体1催化系统开发了一种有效的无溶剂方案，用于芳基和杂芳基氯化物与伯胺和仲胺的布赫瓦尔德-哈特维格交叉偶联反应。值得注意的是，催化体系还可以在水性条件下有效地催化反应。