2-(2-methylbenzyl)-1,2,3,4-tetrahydroisoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-methylbenzyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(2-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline；2-[(2-methylphenyl)methyl]-3,4-dihydro-1H-isoquinoline
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: OIRNNCBLHZHTQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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-(2-methylbenzyl)-1,2,3,4-tetrahydroisoquinoline 在 三氟化硼乙醚 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以57%的产率得到1,2,3,4-四氢-1-[(2-甲基苯基)甲基]异喹啉
  参考文献：
  名称：

  BF 3络合的N-烯丙基和芳基四氢异喹啉的阴离子重排

  摘要：

  BF 3络合的N-烯丙基和N-苄基四氢异喹啉在-20°至0°的THF中与仲-BuLi反应，生成l-取代的四氢异喹啉。

  DOI：

  10.1016/0040-4039(95)01745-4
• 作为产物：
  描述：

  四氢异喹啉 、 2-甲基苄溴 在 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 mineral oil 为溶剂， 以88%的产率得到2-(2-methylbenzyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  亚磷酸二乙酯促进四氢异喹啉电化学氧化为 3,4-二氢异喹啉-1(2H)-酮

  摘要：

  已开发出一种亚磷酸二乙酯介导的电化学氧化策略，用于在温和条件下从四氢异喹啉合成 3,4-二氢异喹啉-1(2H)-酮。该协议为在未分割的单元格中构建 C=O 键提供了一种环保且简单的方法。

  DOI：

  10.1055/s-0039-1690704

文献信息

• Gold Catalyzed Photoredox C1‐Alkynylation of <i>N</i> ‐Alkyl‐1,2,3,4‐tetrahydroisoquinolines by 1‐Bromoalkynes with UVA LED Light
  作者：Yichao Zhao、Jianwen Jin、Philip Wai Hong Chan

  DOI：10.1002/adsc.201801289

  日期：2019.3.15

  A synthetic method that combines [Au2(μ‐dppm)2]Cl2 (dppm=bis(diphenylphosphanyl)methane) and UVA LED (LED=light emitting diode) light (365 nm) to catalyze the regioselective C1‐alkynylation of N‐alkyl‐1,2,3,4‐tetrahydroisoquinolines (THIQs) with alkynyl bromides is described. The reaction mechanism was delineated to involve a reductive quench pathway to generate the two posited radical species of the

  一种合成方法，将[Au 2（μ-dppm）2 ] Cl 2（dppm =双（二苯基膦基）甲烷）和UVA LED（LED =发光二极管）光（365 nm）结合起来，催化N的区域选择性C1-炔基化描述了烷基，1,2,3,4,4-四氢异喹啉（THIQs）与炔基溴化物的关系。划定了反应机理，涉及一个还原性淬灭途径，以生成含氮杂环和有机卤化物的两个正自由基基团。相反，自由基通过有人建议在类似1-碘炔的对照实验中使用氧化猝灭途径。这种碳-碳键形成策略的有用性还通过将其应用于阿片类镇痛药甲氧磷的形式合成和原小ber碱生物碱衍生物的合成而得到了证明。
• Designing analogs of ticlopidine, a wall teichoic acid inhibitor, to avoid formation of its oxidative metabolites
  作者：Maya A. Farha、Kalinka Koteva、Robert T. Gale、Edward W. Sewell、Gerard D. Wright、Eric D. Brown

  DOI：10.1016/j.bmcl.2013.12.069

  日期：2014.2

  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.
• 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.
• Diethyl Phosphite Promoted Electrochemical Oxidation of Tetrahydroisoquinolines to 3,4-Dihydroisoquinolin-1(2H)-ones
  作者：Wenxia Xie、Bowen Gong、Shulin Ning、Nian Liu、Zhuoqi Zhang、Xin Che、Lianyou Zheng、Jinbao Xiang

  DOI：10.1055/s-0039-1690704

  日期：2019.11

  A diethyl phosphite mediated electrochemical oxidation strategy for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones from tetrahydroisoquinolines under mild conditions has been developed. This protocol provides an environmentally friendly and simple way for the construction of C=O bonds in an undivided cell unit.

  已开发出一种亚磷酸二乙酯介导的电化学氧化策略，用于在温和条件下从四氢异喹啉合成 3,4-二氢异喹啉-1(2H)-酮。该协议为在未分割的单元格中构建 C=O 键提供了一种环保且简单的方法。