N-苄基-3-吡啶胺 | 114081-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-3-吡啶胺
• 英文名称: N-(3-pyridine)benzylamine
• 英文别名: N-benzylpyridin-3-amine；N-benzyl-3-aminopyridine；3-(benzylamino)pyridine；N-benzylpyridine-3-amine；N-benzyl-(3-pyridyl)amine；N-(3-pyridyl)-benzylamine
• CAS: 114081-08-2
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: SQMRJGGCCLWSQR-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  330.8±17.0 °C(Predicted)
• 密度：
  1.131±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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  N-苄基-3-吡啶胺 在 sodium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 2.5h， 生成 4-(N-benzyl-N-pyridin-3-ylaminomethyl)-2-(2-methylphenyl)benzoic acid
  参考文献：
  名称：

  Second-Generation Peptidomimetic Inhibitors of Protein Farnesyltransferase Demonstrating Improved Cellular Potency and Significant in Vivo Efficacy

  摘要：

  The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core aryl ring resulted in inhibitors of equal or less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumorderived cell line.

  DOI：

  10.1021/jm9901935
• 作为产物：
  描述：

  1-phenyl-N-(pyridine-3-yl)methaneimine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-苄基-3-吡啶胺
  参考文献：
  名称：

  Second-Generation Peptidomimetic Inhibitors of Protein Farnesyltransferase Demonstrating Improved Cellular Potency and Significant in Vivo Efficacy

  摘要：

  The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core aryl ring resulted in inhibitors of equal or less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumorderived cell line.

  DOI：

  10.1021/jm9901935

文献信息

• A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization–Fluorination of Dithiocarbamates
  作者：Kiyoshi Kanie、Katsuya Mizuno、Manabu Kuroboshi、Tamejiro Hiyama

  DOI：10.1246/bcsj.71.1973

  日期：1998.8

  conditions. When this reaction was applied to dithiocarbamates ArN(R)CS2Me at higher temperatures, the trifluoromethylation was accompanied by halogen substitution at the p-position of the Ar group. The synthesis of trifluoromethyl-substituted adenosine is also described.

  三氟甲胺很容易从二硫代氨基甲酸酯通过由四丁基二氢三氟化铵和 N-卤代酰亚胺组成的试剂系统在温和条件下合成。当该反应在较高温度下应用于二硫代氨基甲酸酯 ArN(R)CS2Me 时，三氟甲基化伴随着 Ar 基团对位的卤素取代。还描述了三氟甲基取代的腺苷的合成。
• Tungsten‐Catalyzed Direct <i>N</i> ‐Alkylation of Anilines with Alcohols
  作者：Xiao‐Bing Lan、Zongren Ye、Chenhui Yang、Weikang Li、Jiahao Liu、Ming Huang、Yan Liu、Zhuofeng Ke

  DOI：10.1002/cssc.202002830

  日期：2021.2.5

  tungsten‐catalyzed N‐alkylation reaction of anilines with primary alcohols via BH/HA. This phosphine‐free W(phen)(CO)4 (phen=1,10‐phenthroline) system was demonstrated as a practical and easily accessible in‐situ catalysis for a broad range of amines and alcohols (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system can tolerate numerous functional groups,

  非贵金属介导化学的实施是均相催化的主要目标。作为一种简单，可持续的合成方法，借用氢/氢自转移（BH / HA）反应在非贵金属催化剂的开发中引起了极大的关注。在此，我们报道了苯胺与伯醇通过BH / HA的钨催化N烷基化反应。这种无膦的W（phen）（CO）4（phen = 1,10-吩咯啉）系统被证明是一种实用且易于就地获得的系统催化作用的胺和醇种类繁多（多达49个实例，包括16个以前未公开的产品）。值得注意的是，该钨系统可以耐受许多官能团，特别是具有位阻取代基或杂原子的具有挑战性的底物。还提供了基于实验和计算研究的力学见解。
• [(PPh₃)₂NiCl₂]-Catalyzed C–N Bond Formation Reaction via Borrowing Hydrogen Strategy: Access to Diverse Secondary Amines and Quinolines
  作者：S. N. R. Donthireddy、Vipin K. Pandey、Arnab Rit

  DOI：10.1021/acs.joc.1c00510

  日期：2021.5.7

  mono-N-alkylation of (hetero)aromatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine (5b) and mepyramine (5c), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy

  发现可商购的[（PPh 3）2 NiCl 2 ]是一种有效的催化剂，用于（杂）芳族胺的单N-烷基化，它利用醇来传递各种仲胺，包括药物中间体氯吡胺（5b）和甲吡胺（5c），通过借用氢的策略，收率极高（高达97％）。该方法在1 mol％的低催化剂负载量和较短的反应时间下，具有广泛的底物范围，具有优异的活性（TON高达10000）。此外，该策略还成功地沿无受体脱氢途径获得了各种喹啉衍生物。
• Palladium-Catalyzed<i>N-</i>Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology
  作者：Xiaochun Yu、Lan Jiang、Qiang Li、Yuanyuan Xie、Qing Xu

  DOI：10.1002/cjoc.201200462

  日期：2012.10

  reactions of amines/amides with alcohols in the past. By employing the aerobic relay race methodology with Pd‐catalyzed aerobic alcohol oxidation being a more effective protocol for alcohol activation, ligand‐free homogeneous palladiums are successfully used as active catalysts in the dehydrative N‐alkylation reactions, giving high yields and selectivities of the alkylated amides and amines. Mechanistic

  可能是因为均相钯催化剂不是典型的借用氢催化剂，因此配体在常规厌氧条件下不能有效活化催化剂，因此过去从未将其用于胺/酰胺与醇的N-烷基化反应中。通过采用好氧接力竞赛方法，并以Pd催化的好氧醇氧化作为更有效的醇活化方案，无配体的均相钯已成功地用作脱水N-烷基化反应中的活性催化剂，从而提供了高收率和高选择性的烷基化酰胺和胺。机理研究表明，该反应很可能是通过我们最近发现并提出的新型中继竞争机制进行的。
• Copper-catalyzed direct amination of benzylic hydrocarbons and inactive aliphatic alkanes with arylamines
  作者：Hua Yao、Bo Xie、Xiaoyang Zhong、Shengzhou Jin、Sen Lin、Zhaohua Yan

  DOI：10.1039/d0ob00491j

  日期：——

  A new synthetic method toward direct C-N bond formation through saturated C-H amination of benzylic hydrocarbons and inactive aliphatic alkanes with primary aromatic amines under an inexpensive catalyst/oxidant (Cu/DTBP) system has been developed. Both aminopyridines and anilines could react smoothly with primary and secondary benzylic C-H substrates or cyclohexane to form the corresponding aromatic

  在廉价的催化剂/氧化剂（Cu / DTBP）系统下，已经开发出一种新的合成方法，该方法可通过苄基烃和惰性脂肪族烷烃与伯芳族胺的饱和CH胺化直接形成CN键。氨基吡啶和苯胺均可与伯和仲苄基CH底物或环己烷顺利反应，以中等至良好的收率形成相应的芳族仲胺。该协议的优点是宽泛的官能团耐受性和使用现成的原料。