N-o-tolyl-3-aminopyridine

• 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: N-o-tolyl-3-aminopyridine
• 英文别名: Pyridin-3-yl-o-tolyl-amine；[3]pyridyl-o-tolyl-amine；N-(2-methylphenyl)pyridin-3-amine
• 化学式: C₁₂H₁₂N₂
• mdl: MFCD09908111
• 分子量: 184.241
• InChiKey: AGLLDRVVVSMSDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(iodopentyl) cyclohexane 、 N-o-tolyl-3-aminopyridine 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 生成
  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 、 邻甲苯胺 在 C₄₈H₅₆ClN₃Pd 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到N-o-tolyl-3-aminopyridine
  参考文献：
  名称：

  健壮的对乙酰氨基咪唑亚丙基四环四环化合物：高效的N-杂芳基氯化物胺化催化剂

  摘要：

  已经成功开发了一系列健壮的N杂环卡宾Palladacycles。这些显示出高催化活性和对具有挑战性的N-杂芳基氯化物的选择性。不同的伯胺和仲胺与该催化体系完全相容。值得注意的是，在我们的催化转化中使用伯胺时，没有检测到双胺化产物。此外，该协议已成功扩展到合成罗格列酮，一种用于糖尿病的临床药物，突出了其潜在的药物可行性。

  DOI：

  10.1002/asia.201700877

文献信息

• Hypervalent Iodine(III) in Direct Oxidative Amination of Arenes with Heteroaromatic Amines
  作者：Srimanta Manna、Polina O. Serebrennikova、Irina A. Utepova、Andrey P. Antonchick、Oleg N. Chupakhin

  DOI：10.1021/acs.orglett.5b02320

  日期：2015.9.18

  coupling of electron-rich arenes with amino derivatives of electron-deficient heterocycles providing rapid access to scaffolds of bioactive compounds and is based on the application of the hypervalent iodine(III) reagent as an oxidant. Regioselective functionalization of C–H bonds of arenes by the formation of C–N bonds under organocatalytic conditions was demonstrated.

  已经开发了在无金属条件下胺化简单的非官能化芳烃的新颖，温和且实用的方法。该方法允许将富电子芳烃与缺电子杂环的氨基衍生物偶联，从而快速进入生物活性化合物的支架，并且基于高价碘（III）试剂作为氧化剂的应用。证明了在有机催化条件下，通过形成C–N键，芳烃的C–H键具有区域选择性功能。
• Biphenyl sulfonic acid ligands for catalytic C-N cross coupling of aryl halides with anilines and secondary amines
  作者：Bärbel Wittel、Till Vogel、Heiko Scharl、Sven Nerdinger、Bernd Lehnemann、Andreas Meudt、Victor Snieckus

  DOI：10.1016/j.bmc.2018.07.028

  日期：2018.8

  The use of two biphenyl sulfonic acid ligands for the catalytic C-N cross coupling of aryl halides with anilines, 3-aminopyridine, and secondary amines is reported. Our results represent a significant improvement compared to state of the art methods especially with regards to the removal of palladium.

  据报道，使用两种联苯磺酸配体将芳基卤化物与苯胺，3-氨基吡啶和仲胺进行CN交叉催化交联。与现有技术方法相比，我们的结果代表了重大改进，尤其是在去除钯方面。
• Well-defined NHC–Pd(II)–Im (NHC=N-heterocyclic carbene; Im=1-methylimidazole) complex catalyzed C–N coupling of primary amines with aryl chlorides
  作者：Lei Zhu、Yue-Mei Ye、Li-Xiong Shao

  DOI：10.1016/j.tet.2012.01.008

  日期：2012.3

  We report herein a well-defined NHC-Pd(II)-Im(NHC=N-heterocyclic carbene; Im=1-methylimidazole) complex catalyzed C-N coupling of primary amines with aryl chlorides. Under the optimal reaction conditions, a variety of primary amines can be coupled with aryl chlorides to give the amination products in good to high yields within 4 h. It is worthy of noting here that the NHC-Pd(II)-Im complex showed especially high catalytic activity toward challenging sterically hindered substrates including both of aryl amines and aryl chlorides. In addition, alkyl amines were also proved to be suitable reaction partners to give the corresponding amination products in good to high yields. (C) 2012 Elsevier Ltd. All rights reserved.
• �ber das 9-Methyl-3-carbolin und das 6-Methyl-3-carbolin
  作者：K. Eiter、Angela Nezval

  DOI：10.1007/bf00903042

  日期：——
• PEPTIDE INHIBITORS OF SELECTIN BINDING
  申请人：CENTOCOR INC.

  公开号：EP0656904A1

  公开（公告）日：1995-06-14