1-<2-Fluor-phenyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolin | 412958-64-6

• 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: 1-<2-Fluor-phenyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolin
• 英文别名: 1-(2-fluoro-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline；1-(2-Fluorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 412958-64-6
• 化学式: C₁₇H₁₈FNO₂
• mdl: MFCD00420208
• 分子量: 287.334
• InChiKey: OSOHYOOOJHCIHK-UHFFFAOYSA-N

物化性质

• 沸点：
  385.8±42.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)
• 溶解度：
  >43.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-<2-Fluor-phenyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolin 在 N,N-二异丙基乙胺 作用下， 生成 dimethyl (2E)-2-[(ethyl)(2-{2-[(2-fluorophenyl)(methoxy)methyl]-4,5-dimethoxyphenyl}ethyl)amino]but-2-enedioate
  参考文献：
  名称：

  使用活化炔烃串联扩增1-芳基-四氢异喹啉中的四氢吡啶环-一种新的有效合成苯并偶氮化合物

  摘要：

  四氢异喹啉图3a - ë后行哌啶环活化的炔烃的作用下增大，给予benzoazocines 4，5和7 - 11以高收率。

  DOI：

  10.1016/j.tetlet.2006.04.151
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 4.0h， 生成 1-<2-Fluor-phenyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolin
  参考文献：
  名称：

  1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro

  摘要：

  A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1-36) were synthesized via Pictet-Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1(IIIB) in C8166 cell cultures by MTT method for the first time. The results of the anti-HIV screening revealed that 6,7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities. Compounds 6, 24, and 36 showed potent anti-HIV activities with EC50 values of 8.2, 4.6, and 5.3 mu M respectively, and the cytotoxicities (CC50) of these three compounds were 784.3, 727.3, and 687.3 mu M, which resulted in SI values larger than 95, 159, and 130 respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.040

文献信息

• Synthesis of Benzoazocines from Substituted Tetrahydroisoquinolines and Activated Alkynes in a Tetrahydropyridine Ring Expansion
  作者：Leonid G. Voskressensky、Anna V. Listratova、Tatiana N. Borisova、Grigoriy G. Alexandrov、Alexey V. Varlamov

  DOI：10.1002/ejoc.200700602

  日期：2007.12

  Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  四氢异喹啉在乙腈或甲醇中存在活化炔烃的情况下经历串联哌啶环扩大，以高产率生产四氢苯并[d]偶氮辛。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• 1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro
  作者：Pi Cheng、Ning Huang、Zhi-Yong Jiang、Quan Zhang、Yong-Tang Zheng、Ji-Jun Chen、Xue-Mei Zhang、Yun-Bao Ma

  DOI：10.1016/j.bmcl.2008.02.040

  日期：2008.4

  A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1-36) were synthesized via Pictet-Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1(IIIB) in C8166 cell cultures by MTT method for the first time. The results of the anti-HIV screening revealed that 6,7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities. Compounds 6, 24, and 36 showed potent anti-HIV activities with EC50 values of 8.2, 4.6, and 5.3 mu M respectively, and the cytotoxicities (CC50) of these three compounds were 784.3, 727.3, and 687.3 mu M, which resulted in SI values larger than 95, 159, and 130 respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Tandem enlargement of the tetrahydropyridine ring in 1-aryl-tetrahydroisoquinolines using activated alkynes—a new and effective synthesis of benzoazocines
  作者：Leonid G. Voskressensky、Tatiana N. Borisova、Anna V. Listratova、Larisa N. Kulikova、Alexander A. Titov、Alexey V. Varlamov

  DOI：10.1016/j.tetlet.2006.04.151

  日期：2006.7

  Tetrahydroisoquinolines 3a–e underwent piperidine ring enlargement under the action of activated alkynes, giving benzoazocines 4, 5 and 7–11 in high yields.

  四氢异喹啉图3a - ë后行哌啶环活化的炔烃的作用下增大，给予benzoazocines 4，5和7 - 11以高收率。