N²-cyclohexylpyridine-2,3-diamine | 41082-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N²-cyclohexylpyridine-2,3-diamine
• 英文别名: 3-amino-2-cyclohexylamino-pyridine；3-amino-2-cyclohexylaminopyridine；N²-cyclohexyl-pyridine-2,3-diyldiamine；N²-Cyclohexyl-pyridin-2,3-diyldiamin；N2-Cyclohexyl-2,3-pyridinediamine；2-(Cyclohexylamino)-3-aminopyridin；2-N-cyclohexylpyridine-2,3-diamine
• CAS: 41082-18-2
• 化学式: C₁₁H₁₇N₃
• 分子量: 191.276
• InChiKey: QXLDNORQKZJMBV-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  190 °C(Press: 12 Torr)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N²-cyclohexylpyridine-2,3-diamine 在 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 叔丁基锂 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， -78.0~110.0 ℃ 、200.0 kPa 条件下， 反应 2.48h， 生成 3-cyclohexyl-2-p-tolyl-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Microwave enhanced Suzuki coupling: a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines

  摘要：

  A modified approach for the synthesis of 3-substituted 2-aryl/heteroaryl imidazo[4,5-b]pyridines utilising palladium catalysed cross-coupling reactions under microwave enhanced conditions has been achieved. utilisation of (A-(ta)phos)(2)PdCl2-catalysed cross-coupling reactions enables rapid derivatization of this (imidazo[4,5-b]pyridines) pharmaceutically relevant core. This catalytic system is compatible with a broad spectrum of arylboronic acids electron rich, electron poor, and heteroarylboronic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.051
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、344.75 kPa 条件下， 生成 N²-cyclohexylpyridine-2,3-diamine
  参考文献：
  名称：

  Regioselective N-alkylation of some imidazole-containing heterocycles and their in vitro anticancer evaluation

  摘要：

  Imidazole-containing heterocycles: Imidazopyridines, imidazopyrimidines and imidazopyra-zines can exist more tautomeric forms than benzimidazoles. Their regioselectivities were determined for N-alkylations with 4-fluorobenzyl bromide under basic conditions (K2CO3) in DMF. We observed that, regioisomers were mainly formed as a mixture in this reaction and N-benzylation occurs at a higher ratio on six membered heterocycles. Their structural assignments were made with the use of two-dimensional H-1-H-1 NOE (nuclear overhauser effect spectroscopy, NOESY). Complementary structural informationwas provided by 2D-HMBC spectra of the compounds. Synthesized compounds were tested for in vitro cytotoxic activities against Human colon cancer cell line (HCT-116) and leukemia cell lines (K562 and HL-60) by MTT test. Among them, imidazopyridine analogue 10, bearing bromine atom at the C-6 position of the pyridine moiety, gave the lowest IC50 value with 6-7 mu g/mL against all three cancer cell lines. (C) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.127673

文献信息

• Imidazopyridine derivatives, preparation method and pharmaceutical compositions containing same
  申请人：Rault Sylvain

  公开号：US20060069117A1

  公开（公告）日：2006-03-30

  Compounds of formula (I): wherein: R 1 represents hydrogen, halogen, alkyl, polyhaloalkyl, cyano, nitro, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, R 2 represents hydrogen, alkyl, an optionally substituted aryl, optionally substituted heteroaryl, or R 20 —C(X)— wherein: R 20 represents alkyl, alkoxy, amino, alkylamino, dialkylamino, optionally substituted aryl or optionally substituted heteroaryl, X represents oxygen, sulphur, or NR 21 wherein R 21 represents hydrogen or alkyl, R 3 represents hydrogen atom or alkyl, n represents integer from 1 to 6 inclusive, the representation its enantiomers, diastereoisomers and also addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful as AMPK activators.

  化学式为（I）的化合物：其中：R1代表氢、卤素、烷基、多卤代烷基、氰基、硝基、羟基羧酸酯基、烷氧羧酸酯基、氨基羧酸酯基、烷基氨基羧酸酯基或二烷基氨基羧酸酯基，R2代表氢、烷基、可选取代芳基、可选取代杂环基或R20—C（X）—，其中：R20代表烷基、烷氧基、氨基、烷基氨基、二烷基氨基、可选取代芳基或可选取代杂环基，X代表氧、硫或NR21，其中R21代表氢或烷基，R3代表氢原子或烷基，n代表从1到6的整数，包括其对映体、非对映异构体以及与药学上可接受的酸或碱形成的加合物，以及含有它们的药物产品，其作为AMPK激活剂是有用的。
• Ethoxymethylenemalonates and Malononitriles (EMM reagents) as formic acid equivalents: Synthesis of fused-imidazoles under neutral or mildly acidic con
  作者：Barb E. Segelstein、Bert L. Chenard、John E. Macor、Ronald J. Post

  DOI：10.1016/s0040-4039(00)91957-9

  日期：1993.3

  The use of ethoxymethylenemalonates and malononitriles (EMM reagents)for the efficient synthesis of fused imidazoles and related compounds is described.
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