4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline | 25771-98-6

• 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: 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 4-(4-chloro-phenyl)-2-methyl-1,2,3,4-tetrahydro-isoquinoline；2-Methyl-4-p-chlorphenyl-1,2,3,4-tetrahydroisochinolin；4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1H-isoquinoline
• CAS: 25771-98-6
• 化学式: C₁₆H₁₆ClN
• 分子量: 257.763
• InChiKey: UIVAIANIXTWVHO-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：
  1
• 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：

  4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 在 Chiracel AD column 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 (4S)-4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1H-isoquinoline 、 (4R)-4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors

  摘要：

  Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.050
• 作为产物：
  描述：

  苯亚甲基甲胺 在 sodium tetrahydroborate 、 硫酸 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 22.33h， 生成 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors

  摘要：

  Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.050

文献信息

• Synthesis of 6,12-Methanodibenzo[<i>c</i>,<i>f</i>]azocines and 4-Aryltetrahydroisoquinolines from Aromatic Aldehydes
  作者：Evgeny M. Buev、Maxim A. Stepanov、Vladimir S. Moshkin、Vyacheslav Y. Sosnovskikh

  DOI：10.1021/acs.orglett.9b04401

  日期：2020.1.17

  A methodology for the synthesis of 7,12-dihydro-5H-6,12-methanodibenzo[c,f]azocines from aromatic aldehydes and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine using catalysis by trifluoroacetic and perchloric acids is described. The developed protocol was applied for the synthesis of N-unsubstituted and N-methyl-4-aryltetrahydroisoquinolines.

  描述了使用三氟乙酸和高氯酸催化从芳族醛和N-（甲氧基甲基）-N-（三甲基甲硅烷基甲基）苄胺合成7,12-二氢-5H-6,12-甲基二苯并[c，f]偶氮嗪的方法。该开发的方案适用于N-未取代和N-甲基-4-芳基四氢异喹啉的合成。
• A facile synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines
  作者：Min Hu、Peter R. Guzzo、Congxiang Zha、Kassoum Nacro、Yuh-Lin Yang、Carla Hassler、Shuang Liu

  DOI：10.1016/j.tetlet.2011.12.022

  日期：2012.2

  versatile palladium catalyzed α-arylation between dihydroisoquinolinones and various aryl halides is described. Combined with borane reduction, it provides a convenient way to prepare 4-aryl-1,2,3,4-tetrahydroisoquinolines.

  描述了一种在二氢异喹啉酮与各种芳基卤化物之间的简便且通用的钯催化的α-芳基化反应。结合硼烷还原，它提供了一种制备4-芳基-1,2,3,4-四氢异喹啉的简便方法。
• New Reduction Reaction of Benzylic Alcohols with Acid and Proof of the Intermolecular Hydride Shift Mechanism
  作者：Masaru Kihara、Jun-ichi Andoh、Chiaki Yoshida

  DOI：10.3987/com-99-8786

  日期：——

  The new reduction reaction of the hydroxy groups of 4-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinolines (1) to the corresponding alkanes (2) with mineral and Lewis acids is reported. A stereoselective intermolecular hydride shift mechanism of the reduction was proved by reaction of the deuterated derivateives (14 and 15) of 1a with 10N HCl-C2H5OH and BBr3 in CH3CN.
• 4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors
  作者：Anthony D. Pechulis、James P. Beck、Matt A. Curry、Mark A. Wolf、Arthur E. Harms、Ning Xi、Chet Opalka、Mark P. Sweet、Zhicai Yang、A. Samuel Vellekoop、Andrew M. Klos、Peter J. Crocker、Carla Hassler、Mia Laws、Douglas B. Kitchen、Mark A. Smith、Richard E. Olson、Shuang Liu、Bruce F. Molino

  DOI：10.1016/j.bmcl.2012.09.050

  日期：2012.12

  Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41. (C) 2012 Elsevier Ltd. All rights reserved.