2-aminomethyl-1,2,3,4-tetrahydroquinoline | 84393-46-4

• 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: 2-aminomethyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (1,2,3,4-tetrahydroquinolin-2-yl)methanamine；(+/-)-2-Aminomethyl-1,2,3,4-tetrahydro-chinolin；C-(1,2,3,4-tetrahydro-[2]quinolyl)-methylamine；C-(1,2,3,4-Tetrahydro-[2]chinolyl)-methylamin；1,2,3,4-tetrahydroquinolin-2-ylmethanamine
• CAS: 84393-46-4
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: NBDSHMSFKIDUPF-UHFFFAOYSA-N

物化性质

• 沸点：
  166-168 °C(Press: 11 Torr)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-aminomethyl-1,2,3,4-tetrahydroquinoline 以 乙醇 为溶剂， 反应 4.5h， 生成 1-(2-phenylethenyl)-3,3a,4,5-tetrahydroimidazo<1,5-a>quinoline
  参考文献：
  名称：

  Jones, Raymond C. F.; Smallridge, Mark J.; Chapleo, Christopher B., Journal of the Chemical Society. Perkin transactions I, 1990, # 2, p. 385 - 391

  摘要：

  DOI：
• 作为产物：
  描述：

  N-((1,2,3,4-tetrahydroquinolin-2-yl)methyl)benzamide 在 盐酸 作用下， 生成 2-aminomethyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  死于1-Benzoyl-2-cyan-1,2-dihydrochinolin的Hydrierung von。（Reissert'scherKörper）我

  摘要：

  DOI：

  10.1002/hlca.19370200128

文献信息

• Zinc(<scp>ii</scp>)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of<i>N</i>-propargylanilines with diverse carbon pronucleophiles: facile access to functionalized tetrahydroquinolines
  作者：Guangzhe Li、Chengdong Wang、Yueqing Li、Kun Shao、Guo Yu、Shisheng Wang、Xiuhan Guo、Weijie Zhao、Hiroyuki Nakamura

  DOI：10.1039/d0cc02921a

  日期：——

  Redox cross-dehydrogenative coupling ofN-propargylanilines with diverse carbon pronucleophiles offers a general and efficient synthetic method to construct functionalized tetrahydroquinolines.

  氧化还原交叉脱氢偶联法将各种碳原核亲核试剂与N-丙炔基苯胺进行偶联，提供了一种通用高效的合成方法，用于构建官能化四氢喹啉。
• 一类2-取代四氢喹啉化合物及其衍生物、制备方法和应用
  申请人：大连理工大学

  公开号：CN111233761B

  公开（公告）日：2022-01-14

  本发明属于药物与化工技术领域，涉及一类2‑取代四氢喹啉化合物及其衍生物、制备方法和应用。本发明制备得到的2‑取代四氢喹啉化合物及其衍生物，具有抗疟活性，可以作为多种药用关键中间体，可以应用于制备抗肿瘤药物和HIF‑1抑制剂，制备方法绿色、简化和高效。
• FUSED THIOPHENE DERIVATIVES AS MEK INHIBITORS
  申请人：Laing Victoria Elizabeth

  公开号：US20090264411A1

  公开（公告）日：2009-10-22

  A series of 4,5,6,7-tetrahydrothieno[2,3-c]azepin-8-one derivatives, and analogues thereof, which are substituted in the 2-position by a substituted anilino moiety, being selective inhibitors of human MEK (MAPKK) enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, proliferative (including oncological) and nociceptive conditions.

  一系列4,5,6,7-四氢噻吩[2,3-c]唑啉-8-酮衍生物及其类似物，在2位被取代的苯胺基团取代下，是选择性抑制人类MEK（MAPKK）酶的，因此在医学上具有益处，例如在治疗炎症、自身免疫、心血管、增生（包括肿瘤）和疼痛性疾病方面。
• Process for the production of CCR2 receptor antagonists and intermediates thereof
  申请人：BOEHRINGER INGELHEIM INTERNATIONAL GMBH

  公开号：EP2816040A1

  公开（公告）日：2014-12-24

  The present invention relates to a process for the production of novel antagonists for CCR2 (CC chemokine receptor 2) of formula (I) from 6-Chloro-pyrimidine-methanone intermediates. Formula (I): Specifically claimed 6-chloropyrimidine-methanone intermediates are:

  本发明涉及一种从 6-氯嘧啶-甲酮中间体生产式（I）的新型 CCR2（CC 趋化因子受体 2）拮抗剂的工艺。 式 (I)： 具体要求的 6-氯嘧啶-甲酮中间体是：
• Highly Potent and Selective MT₂ Melatonin Receptor Full Agonists from Conformational Analysis of 1-Benzyl-2-acylaminomethyl-tetrahydroquinolines
  作者：Gilberto Spadoni、Annalida Bedini、Simone Lucarini、Michele Mari、Daniel-Henri Caignard、Jean A. Boutin、Philippe Delagrange、Valeria Lucini、Francesco Scaglione、Alessio Lodola、Franca Zanardi、Daniele Pala、Marco Mor、Silvia Rivara

  DOI：10.1021/acs.jmedchem.5b01066

  日期：2015.9.24

  Molecular superposition models guided the design of novel melatonin receptor ligands characterized by a 2-acylaminomethyltetrahydroquinoline scaffold. Starting from the structure of N-anilinoethylamide ligands, the flexible chain was conformationally constrained to reproduce the bioactive conformation of melatonin. Structure activity relationships were investigated, focusing on the substituent at the nitrogen atom, the position of the methoxy group, and the replacement of the amide side chain by urea and thiourea groups. The compounds were tested for binding affinity and intrinsic activity at human MT1, and MT2 receptors. Structural optimization resulted in N-[(1-benzyl-1,2,3,4-tetrahydro-5-methoxyquinolin-2-yl)methyl]propionamide (UCM1014), with picomolar MT2 binding affinity (K-i = 0.001 nM), more than 10000-fold selectivity over the MT1 receptor, and a full agonist profile (GTP gamma S test), being the most potent MT2-selective full agonist reported to date. Molecular dynamics simulations provided a rationale for high binding affinity, stereoselectivity, and agonist behavior of these novel melatonin receptor ligands based on superposition models and conformational preference.