1-(氨甲基)-1,2,3,4-四氢异喹啉 | 84500-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 1-(氨甲基)-1,2,3,4-四氢异喹啉
• 英文名称: 1-(1,2,3,4-tetrahydro-1-isoquinolinyl)methanamine
• 英文别名: (1,2,3,4-tetrahydroisoquinolin-1-yl)methanamine；1-(aminomethyl)-1,2,3,4-tetrahydroisoquinoline；1-aminomethyl-1,2,3,4-tetrahydroisoquinoline；DC_BD245；C-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-methylamine；C-(1,2,3,4-tetrahydro-[1]isoquinolyl)-methylamine；1,2,3,4-Tetrahydroisoquinolylmethylamine；1,2,3,4-tetrahydroisoquinolin-1-ylmethanamine
• CAS: 84500-70-9；790152-57-7
• 化学式: C₁₀H₁₄N₂
• mdl: MFCD00600390
• 分子量: 162.235
• InChiKey: WZZJAYPARCLIPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：

  1-(氨甲基)-1,2,3,4-四氢异喹啉 在 吡啶 、 盐酸 、 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 吡喹酮
  参考文献：
  名称：

  氮与氮的Aza-Henry反应，这是一个尚未充分发现的转变

  摘要：

  进行了将硝基烷烃添加到硝酮中的综合研究。在大量过量的R–NO 2的存在下，以TMAF或TBD为碱，该反应被证明是有效的。相转移催化也得到可接受的产率。硝基乙烷或硝基丙烷提供可异构的非对映异构体的混合物。该反应被用于生物相关化合物的合成。

  DOI：

  10.1002/ejoc.201801823
• 作为产物：
  描述：

  2-benzyl-3,4-dihydroisoquinolin-2-ium bromide 在 palladium on activated charcoal aluminium hydride 、 氢气 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 36.0h， 生成 1-(氨甲基)-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines and their actions at adrenoceptors in vivo and in vitro

  摘要：

  An improved synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines has been developed by using aluminum hydride reduction of 1-cyano-1,2,3,4-tetrahydroisoquinolines. Three 1-(aminomethyl)-6,7-dihydroxytetrahydroisoquinolines were tested for actions at beta adrenoceptors in order to examine a proposed similarity between this series and the related phenylethanolamines. The aminomethyl, (isopropylamino)methyl, and (tert-butylamino)methyl derivatives all showed weak partial agonist activity at beta adrenoceptors and the first also showed weak alpha adrenoceptor agonist activity in vivo. Their low potency implies that the catechol group of THIQ sympathomimetics, such as trimetoquinol, binds differently from that of the natural catecholamines. The protonation behavior of representative aminomethyl-THIQ's was investigated by pKa measurement and 1H and 13C NMR, and the compounds were shown to be substantially monoprotonated, on the exocyclic nitrogen, at physiological pH.

  DOI：

  10.1021/jm00358a010

文献信息

• Synthesis and central nervous system properties of 2-[(alkoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines
  作者：Klaus Weinhardt、Colin C. Beard、Charles Dvorak、Michael Marx、John Patterson、Adolph Roszkowski、Margery Schuler、Stefan H. Unger、Paul J. Wagner、Marshall B. Wallach

  DOI：10.1021/jm00371a011

  日期：1984.5

  midazolines was prepared and evaluated for central nervous system (CNS) effects (antidepressant, anticonvulsant, muscle relaxant, and depressant) in animal models. Some separation of those CNS activities was achieved through substitutions on the phenyl and imidazoline moieties. Halo-substituted phenyl compounds were among the most potent antidepressants in this series, while imidazole N-alkylation

  制备了一系列2-[（（烷氧基羰基）氨基] -4（5）-苯基-2-咪唑啉，并在动物模型中评估了其对中枢神经系统（CNS）的影响（抗抑郁药，抗惊厥药，肌肉松弛药和抑郁药）。这些CNS活性的分离是通过苯基和咪唑啉部分的取代实现的。卤代苯基化合物是该系列中最有效的抗抑郁药，而咪唑N-烷基化所产生的化合物具有增强的抗抑郁作用（失去正翻反射，小鼠行为）。对2-[（（甲氧羰基）氨基] -4（5）-苯基-2-咪唑啉及其母体2-氨基-4（5）-苯基-2-咪唑啉对的体内和体外数据比较表明标题化合物是抑制去甲肾上腺素再摄取的2-氨基-4（5）-苯基-2-咪唑啉的前药。
• Mechanically activated ring-opening reactions of N-acyl-1,2,3,4-tetrahydroisoquinolines derived from the synthesis of praziquantel intermediate
  作者：Jingbo Yu、Zhi Wang、Yang Zhang、Weike Su

  DOI：10.1016/j.tet.2015.06.105

  日期：2015.9

  DDQ-promoted ring-opening reaction of N-chloroacetyl-tetrahydroisoquinoline under ball milling conditions was revealed during the synthesis of Praziquantel. A variety of N-acyl-tetrahydroisoquinolines were then tested to further investigate the reaction, and plausible reaction mechanism was proposed. Ball milling was demonstrated to be an efficient tool to promote this oxidative ring-opening reaction to give

  在吡喹酮的合成过程中，N-氯乙酰基-四氢异喹啉在球磨条件下发生了意想不到的DDQ促进的开环反应。然后测试了各种N-酰基-四氢异喹啉以进一步研究该反应，并提出了合理的反应机理。球磨被证明是一种有效的工具，可以促进这种氧化性开环反应，从而在较短的反应时间内以令人满意的产率提供具有良好选择性的产物。
• [EN] PIPERIDINYL AMINE COMPOUNDS FOR THE TREATMENT OF AUTOIMMUNE DISEASE<br/>[FR] COMPOSÉS DE PIPÉRIDINYL AMINE POUR LE TRAITEMENT D'UNE MALADIE AUTO-IMMUNE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021052892A1

  公开（公告）日：2021-03-25

  The present invention relates to compounds of formula (I), wherein R1, R2, R3, R4 and R5 are as described herein, and their pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

  本发明涉及公式（I）的化合物，其中R1、R2、R3、R4和R5如本文所述，并且它们的药用盐、对映体或二对映体，以及包括该化合物的组合物和使用该化合物的方法。
• Facile synthesis of vicinal diamines via oxidation of N-phenyltetrahydroisoquinolines with DDQ
  作者：Althea S.-K. Tsang、Matthew H. Todd

  DOI：10.1016/j.tetlet.2008.12.101

  日期：2009.3

  aromatic ring and the C1 carbon being stronger than with the N-aryl ring. Reduction of the β-nitroamines to the corresponding novel chiral vicinal diamines are straightforward. Examination of the reaction by 1H NMR spectroscopy suggested that the reaction proceeds via an iminium ion, which then reacts with nitromethane upon work-up. This information was used to shorten the required reaction time.

  N-苯基四氢异喹啉的氧化在DDQ中迅速发生。在环境条件下和在硝基甲烷的存在下，以良好至优异的产率分离出相应的β-硝基胺衍生物。异喹啉和N-苯基取代基的电子性质的变化表明，可以接受广泛的取代基，异喹啉芳族环和C1碳之间的电子连通比N-芳基环更强。将β-硝基胺还原为相应的新型手性邻二胺是直接的。用1检验反应1 H NMR光谱表明该反应通过亚胺离子进行，该亚胺离子随后在处理后与硝基甲烷反应。该信息用于缩短所需的反应时间。
• HETEROCYCLIC COMPOUNDS AND USE THEREOF
  申请人：National Health Research Institutes

  公开号：US20190077786A1

  公开（公告）日：2019-03-14

  Disclosed are compounds of formula (I) below or pharmaceutically acceptable salts thereof: in which each of variables R 1 -R 6 , L, m, and n is defined herein. Also disclosed are a method for treating an opioid receptor-associated condition with a compound of formula (I) and a pharmaceutical composition containing same.

  揭示了下面的化合物的结构式（I）或其药用盐：其中变量R1-R6、L、m和n在此处有定义。还揭示了使用结构式（I）的化合物治疗阿片受体相关疾病的方法，以及含有该化合物的药物组合物。