2-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline | 72809-43-9

• 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-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(2-chloro-benzyl)-1,2,3,4-tetrahydro-isoquinoline；2-(2-Chlorbenzyl)-1,2,3,4-tetrahydro-isochinolin；Cambridge id 5260510；2-[(2-chlorophenyl)methyl]-3,4-dihydro-1H-isoquinoline
• CAS: 72809-43-9
• 化学式: C₁₆H₁₆ClN
• 分子量: 257.763
• InChiKey: FFVHTUGWVKEQQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline 在 四乙基对甲苯磺酸铵 、 亚磷酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以52%的产率得到2-(2-chlorobenzyl)-3,4-dihydroisoquinolin-1(2H)-one
  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
• 作为产物：
  描述：

  四氢异喹啉 、 2-氯苄溴 在 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 mineral oil 为溶剂， 以96%的产率得到2-(2-chlorobenzyl)-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

• Efficient Synthesis of <i>N</i>-Alkyl Tetrahydroisoquinolines by Reductive Amination
  作者：Sukanta Bhattacharyya、Hephzibah Kumpaty

  DOI：10.1055/s-2005-872081

  日期：——

  An expedient access to diverse N-alkyl 1,2,3,4-tetrahydroisoquinolines is reported by reductive amination of aldehydes and ketones with tetrahydroisoquinoline (THIQ) in the presence of Ti(Oi-Pr) 4 and NaBH 4 . The N-alkyl THIQ products were rapidly purified by flow-through catch and release technique using commercially available polymer-supported sulfonic acid, MP-TsOH columns.

  据报道，在 Ti(Oi-Pr) 4 和 NaBH 4 存在下，用四氢异喹啉 (THIQ) 对醛和酮进行还原胺化，可以方便地获得多种 N-烷基 1,2,3,4-四氢异喹啉。N-烷基 THIQ 产品通过流通捕​​获和释放技术使用市售的聚合物负载磺酸 MP-TsOH 柱快速纯化。
• 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.
• US4261998A
  申请人：——

  公开号：US4261998A

  公开（公告）日：1981-04-14
• US4678792A
  申请人：——

  公开号：US4678792A

  公开（公告）日：1987-07-07