N-benzyl-1-(quinolin-2-yl)methanamine | 1042792-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-benzyl-1-(quinolin-2-yl)methanamine
• 英文别名: N-(quinol-2-ylmethyl)-N-benzylamine；N-(quinolin-2-ylmethyl)-N-benzylamine；1-phenyl-N-(quinolin-2-ylmethyl)methanamine
• CAS: 1042792-12-0
• 化学式: C₁₇H₁₆N₂
• mdl: MFCD12630898
• 分子量: 248.327
• InChiKey: CYUODQHXXAEAOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 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-benzyl-1-(quinolin-2-yl)methanamine 在 碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1-phenyl-3-(phenylthio)imidazo[1,5-a]quinoline
  参考文献：
  名称：

  甲基N-杂芳族化合物与胺和氨基酸的电催化分子间C（sp 3）-H / N-H偶联：咪唑基融合N-杂环化合物的获得

  摘要：

  通过阳极氧化，开发了一种有效的NH 4 I介导的甲基N-杂芳族化合物与胺/氨基酸的分子间环化反应，提供了多种具有良好至优异收率的官能化的咪唑并合的N-杂环。该协议的实用性通过容易获得的起始材料，广泛的底物范围，耐水性，可扩展性以及电解产物的多种转化得到证明。

  DOI：

  10.1021/acs.orglett.8b02578
• 作为产物：
  描述：

  1-phenyl-N-(quinolin-2-ylmethylene)methanamine 在 盐酸 、 甲醇 、 三甲氧基磷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 N-benzyl-1-(quinolin-2-yl)methanamine
  参考文献：
  名称：

  新型喹啉-2、-3 和 4-基-（氨基）甲基膦酸酯：酸性条件下喹啉-2 和-4 衍生物中CP 键断裂的合成和研究

  摘要：

  介绍了新的喹啉-（氨基）甲基膦酸、它们的膦酸酯和氧化膦的合成。通过将磷物质亲核加成到喹啉衍生的希夫碱上，有效地获得了所需的新化合物。此外，发现用 HCl 水溶液加热 quinolin-2 和 quinolin-4-yl-(amino)-methylphosphonates 会导致它们分解，导致 CP 键断裂，排斥含磷片段，并形成相应的仲喹啉-2 和喹啉-4-烷基胺。假设了这种裂解的两种替代机制途径。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:617–624, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20704

  DOI：

  10.1002/hc.20704

文献信息

• Redox‐Neutral Metal‐Free Three‐Component Carbonylative Dearomatization of Pyridine Derivatives with CO ₂
  作者：Alessandro Cerveri、Stefano Pace、Magda Monari、Marco Lombardo、Marco Bandini

  DOI：10.1002/chem.201904359

  日期：2019.12.2

  methodology enables the realization of densely functionalized imidazo-pyridinones in high yields (up to 93 %) and excellent chemoselectivity. Combined computational and experimental investigations revealed an unprecedented RCOCl/TBD concerted electrophilic activation of carbon dioxide.

  吡啶-2-甲胺的TBD（1,3,5-三氮杂双环癸-5-烯）辅助的三组分羰基化是通过CO2作为良性CO替代物记录的。氧化还原中性方法能够以高收率（高达93％）和优异的化学选择性实现稠密官能化的咪唑并吡啶酮。组合的计算和实验研究表明，前所未有的RCOCl / TBD协同作用了二氧化碳的亲电活化。
• Synthesis of Cyanide-Functionalized Imidazo[1,5-a]quinolines via Copper-Mediated Aerobic Three-Component Cyclizations
  作者：Cheng-Tao Feng、Hong-Juan Wei、Jing Li、Ya Peng、Kun Xu

  DOI：10.1002/adsc.201801060

  日期：2018.12.21

  A three‐component cyclization of 2‐methylquinolines, trimethylsilyl cyanide, and alkylamines or α‐amino acids mediated by CuSO4 was developed. By employing oxygen as the clean oxidant, cyanated imidazo[1,5‐a]quinolines were constructed with high efficiency for the first time. The loading of CuSO4 could be lowered to 20 mol% with a slightly diminished yield. The synthetic utility of this method is further

  开发了由CuSO 4介导的2-甲基喹啉，三甲基甲硅烷基氰化物和烷基胺或α-氨基酸的三组分环化反应。通过使用氧气作为清洁氧化剂，首次高效率构建了氰化咪唑并[1,5-a]喹啉。CuSO 4的载量可以降低到20摩尔％，收率略有下降。克级合成和敏感官能团的耐受性进一步突出了该方法的合成效用。
• CHROMANYLUREA COMPOUNDS THAT INHIBIT VANILLOID RECEPTOR SUBTYPE 1 (VR1) RECEPTOR AND USES THEREOF
  申请人：Gomtsyan Arthur

  公开号：US20110152250A1

  公开（公告）日：2011-06-23

  Compounds that are antagonists of the VR1 receptor, having formula (I) or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A 1 , A 2 , A 3 , A 4 , R 7 , R 8 , R 9 , X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.

  具有以下式子（I）或其药学上可接受的盐、前药或前药的盐的拮抗VR1受体的化合物，在其中A1、A2、A3、A4、R7、R8、R9、X、Y、Z、L、n和m如本文所定义，并且在抑制VR1受体有益于预防或改善疾病。
• Allosteric Functional Switch of Neurokinin A-Mediated Signaling at the Neurokinin NK2 Receptor: Structural Exploration
  作者：Céline Valant、Emeline Maillet、Jean-Jacques Bourguignon、Bernard Bucher、Valérie Utard、Jean-Luc Galzi、Marcel Hibert

  DOI：10.1021/jm900671k

  日期：2009.10.8

  The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: resting-inactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while CAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator.
• Electrocatalytic Three-Component Reaction: Synthesis of Cyanide-Functionalization Imidazo-Fused <i>N</i>-Heterocycles
  作者：Peng Qian、Zhenghong Zhou、Kangfei Hu、Jiawei Wang、Zhibin Li、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.orglett.9b02317

  日期：2019.8.16

  An electrochemical three-component cyclization was developed under metal-free conditions, which provides a novel and facile approach for the construction of cyanide-functionalization imidazo-fused N-heterocycles. A variety of cyanide-functionalization imidazo-fused N-hetero-cycles can be obtained from easily available methyl N-heteroaromatics, primary alkylamines, and trimethylsilyl cyanide with good to excellent yields. The reaction features a broad scope of substrates, scalability, and mild conditions.