2-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline | 1415507-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(naphthalen-2-ylmethyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1415507-70-8
• 化学式: C₂₀H₁₉N
• 分子量: 273.378
• InChiKey: JDIHSDYOQSSTDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline 以 乙腈 为溶剂， 反应 3.0h， 生成 methyl-(2-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate
  参考文献：
  名称：

  Tropylium促进的四氢异喹啉的氧化功能化。

  摘要：

  四氢异喹啉（THIQ）框架的结构修饰因其在杂环和药物化学中的核心作用而引起有机化学家的极大兴趣。在这里，我们证明了一种有效的无金属方法，可用于THIQs在C1位置的氧化功能化，适用于各种C–C偶联反应。这些反应通过涉及对乙铵离子的氢化物提取进行，然后用亲核试剂淬灭生成的亚胺中间体，从而以优异的效率和令人感兴趣的选择性提供了THIQ衍生物。

  DOI：

  10.1021/acs.joc.7b02584
• 作为产物：
  描述：

  四氢异喹啉 、 2-(氯甲基)萘 以 乙腈 为溶剂， 以80%的产率得到2-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Designing analogs of ticlopidine, a wall teichoic acid inhibitor, to avoid formation of its oxidative metabolites

  摘要：

  The thienopyridine antiplatelet agent, ticlopidine and its analog, clopidogrel, have been shown to potentiate the action of beta-lactam antibiotics, reversing the methicillin-resistance phenotype of methicillin- resistant Staphylococcus aureus (MRSA), in vitro. Interestingly, these thienopyridines inhibit the action of TarO, the first enzyme in the synthesis of wall teichoic acid, an important cell wall polymer in Gram-positive bacteria. In the human body, both ticlopidine and clopidogrel undergo a rapid P450-dependent oxidation into their respective antiplatelet-active metabolites, resulting in very low plasma concentrations of intact drug. Herein, a series of analogs of ticlopidine and clopidogrel that would avoid oxidative metabolism were designed, prepared and evaluated as inhibitors of TarO. Specifically, we replaced the P450-labile thiophene ring of ticlopidine and clopidogrel to a more stable phenyl group to generate 2-(2-chlorobenzyl)-1,2,3,4-tetrahydro-isoquinoline) (6) and (2-chloro-phenyl)-(3,4-dihydro-1H-isoquinolin- 2-yl)-acetic acid methyl ester (22), respectively. The latter molecules displayed inhibitory activity against TarO and formed the basis of a library of analogs. Most synthesized compounds exhibited comparable efficacy to ticlopidine and clopidogrel. So far, it was introduction of a trifluoromethyl group to compound 6, to generate 2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline (13) that exhibited enhanced activity against TarO. Compound 13 represents a novel stable inhibitor of TarO with synergistic impact on b-lactam antibiotics against MRSA and low potential for P-450 metabolism. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.069

文献信息

• Synthesis of tertiary amines by direct Brønsted acid catalyzed reductive amination
  作者：Mohanad A. Hussein、An H. Dinh、Vien T. Huynh、Thanh Vinh Nguyen

  DOI：10.1039/d0cc02955f

  日期：——

  reductive amination reaction of carbonyl compounds. Despite developments of numerous new reductive amination methods in the past few decades, this reaction generally requires non-atom-economic processes with harsh conditions and toxic transition-metal catalysts. Herein, we report simple yet practical protocols using triflic acid as a catalyst to efficiently promote the direct reductive amination reactions

  叔胺是合成化学中普遍存在的有价值的化合物，在有机催化，有机金属配合物，生物过程和药物化学中具有广泛的应用。合成叔胺最常用的途径之一是羰基化合物的还原胺化反应。尽管在过去的几十年中已经开发了许多新的还原胺化方法，但是该反应通常需要具有苛刻条件的非原子经济过程和有毒的过渡金属催化剂。在本文中，我们报告了使用三氟甲磺酸作为催化剂以有效地促进羰基化合物在各种基材上的直接还原胺化反应的简单而实用的方案。还包括该新方法在产生有价值的杂环骨架和多胺中的应用。
• CORROSION INHIBITION
  申请人：SCHLUMBERGER TECHNOLOGY CORPORATION

  公开号：US20180312980A1

  公开（公告）日：2018-11-01

  A corrosion inhibiting compound with a general structure A-B or A-X-B for inhibition of corrosion of steel in acidic solution. A comprises a heterocyclic ring system having a plurality of cyclic Carbon atoms and at least one cyclic Nitrogen atom, wherein the at least one cyclic Nitrogen atom is neutral under neutral conditions and protonatable under acidic conditions. B comprises at least two unsaturated Carbon atoms. B may comprise a ring system or a polymerisable group.

  一种具有一般结构A-B或A-X-B的防腐蚀化合物，用于抑制钢材在酸性溶液中的腐蚀。A包括具有多个环状碳原子和至少一个环状氮原子的杂环系统，其中至少一个环状氮原子在中性条件下是中性的，在酸性条件下可以质子化。B包括至少两个不饱和碳原子。B可以包括一个环系统或一个可聚合基团。
• Corrosion inhibition
  申请人：SCHLUMBERGER TECHNOLOGY CORPORATION

  公开号：US10982337B2

  公开（公告）日：2021-04-20

  A corrosion inhibiting compound with a general structure A-B or A-X-B for inhibition of corrosion of steel in acidic solution. A comprises a heterocyclic ring system having a plurality of cyclic Carbon atoms and at least one cyclic Nitrogen atom, wherein the at least one cyclic Nitrogen atom is neutral under neutral conditions and protonatable under acidic conditions. B comprises at least two unsaturated Carbon atoms. B may comprise a ring system or a polymerisable group.

  一种具有一般结构 A-B 或 A-X-B 的缓蚀化合物，用于抑制钢在酸性溶液中的腐蚀。A 包括一个杂环环系，该环系具有多个环状碳原子和至少一个环状氮原子，其中至少一个环状氮原子在中性条件下呈中性，在酸性条件下可质子化。B 包括至少两个不饱和碳原子。B 可包括一个环系统或一个可聚合基团。
• NOVEL ANTIBACTERIAL COMBINATION THERAPY
  申请人：Brown Eric D.

  公开号：US20140088069A1

  公开（公告）日：2014-03-27

  An antibacterial composition is provided including a combination of a β-lactam antibiotic that has a binding affinity for bacterial penicillin-binding protein 2; and a non-antibiotic compound which may be a thienopyridine or a non-thienopyridine compound. A method of treatment using the composition is also provided.
• [EN] NOVEL ANTIBACTERIAL COMBINATION THERAPY<br/>[FR] NOUVEAU TRAITEMENT COMBINÉ ANTIBACTÉRIEN
  申请人：UNIV MCMASTER

  公开号：WO2012162814A1

  公开（公告）日：2012-12-06

  An antibacterial composition is provided including a combination of a β-lactam antibiotic that has a binding affinity for bacterial penicillin-binding protein 2; and a non-antibiotic compound which may be a thienopyridine or a non-thienopyridine compound. A method of treatment using the composition is also provided.