1-phenyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline | 25200-15-1

• 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-phenyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6-hydroxy-1-phenyl-1,2,3,4-tetrahydro-isoquinoline；1,2,3,4-Tetrahydro-1-phenyl-6-isochinolinol；1-phenyl-1,2,3,4-tetrahydro-isoquinolin-6-ol；1-Phenyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• CAS: 25200-15-1
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: ZCNSVVDWODXGJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline 在 盐酸 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  1-Aryl-1,2,3,4-tetrahydroisoquinolines as potential antimalarials: synthesis, in vitro antiplasmodial activity and in silico pharmacokinetics evaluation

  摘要：

  在这项研究中，通过碱催化的Pictet-Spengler反应合成了21种1-芳基-6-羟基-1,2,3,4-四氢异喹啉（THIQ）类似物，并通过[³H]次黄嘌呤掺入实验对疟原虫进行了体外测试。

  DOI：

  10.1039/c3ra46791k
• 作为产物：
  描述：

  间羟基苯乙胺 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 1-phenyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Catalytic Pictet–Spengler reactions using Yb(OTf)3

  摘要：

  The catalytic Pictet-Spengler reactions proceeded in high yields with high regioselectivity in the presence of a catalytic amount of Yb(OTf)(3) and a dehydrating agent at room temperature. High regioselectivities were obtained in these reactions, and it is suggested that the reactions proceeded under kinetic control. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.018

文献信息

• Calcium-Catalyzed Pictet−Spengler Reactions
  作者：Matthew J. Vanden Eynden、James P. Stambuli

  DOI：10.1021/ol802173r

  日期：2008.11.20

  Pictet-Spengler reactions of m-tyramine and aldehydes produced tetrahydroisoquinolines in the presence of a catalytic amount of Ca[OCH(CF3)2]2. This reaction occurs with a variety of aryl, heteroaryl, and alkyl aldehydes, producing tetrahydroisoquinolines in high yield and with high regioselectivity. This calcium-promoted Pictet-Spengler reaction provides a mild alternative to the traditional Bronsted

  在催化量的Ca [OCH（CF3）2] 2存在下，间苯胺和醛的Pictet-Spengler反应产生四氢异喹啉。该反应与各种芳基，杂芳基和烷基醛发生，以高产率和高区域选择性产生四氢异喹啉。这种钙促进的Pictet-Spengler反应提供了通常用于这些反应的传统布朗斯台德酸的温和替代品。
• Regioselective bromination of <scp>6‐hydroxytetrahydroisoquinolines</scp>
  作者：Ke Wang、Xuan Pan、Kun Peng、Zhan Z. Liu

  DOI：10.1002/jhet.4121

  日期：2020.12

  Regioselective bromination of 6‐hydroxytetrahydroisoquinolines using molecular bromine was disclosed. Treatment of 6‐hydroxytetrahydroisoquinolines with molecular bromine under different temperatures afforded 5‐bromo‐6‐hydroxytetrahydroisoquinolines as sole products in high isolated yield with excellent regioselectivity.

  公开了使用分子溴对6-羟基四氢异喹啉进行区域选择性溴化。在不同温度下用分子溴处理6-羟基四氢异喹啉可得到5-溴-6-羟基四氢异喹啉作为唯一产品​​，分离产率高，具有出色的区域选择性。
• 1-Aryl-1,2,3,4-tetrahydroisoquinolines as potential antimalarials: synthesis, in vitro antiplasmodial activity and in silico pharmacokinetics evaluation
  作者：Joelle Ngo Hanna、Fidele Ntie-Kang、Marcel Kaiser、Reto Brun、Simon M. N. Efange

  DOI：10.1039/c3ra46791k

  日期：——

  In the present study, twenty-one 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline (THIQ) analogues were synthesized by base-catalyzed Pictet–Spengler reaction, and testedin vitroagainstP. falciparumusing the [³H]hypoxanthine incorporation assay.

  在这项研究中，通过碱催化的Pictet-Spengler反应合成了21种1-芳基-6-羟基-1,2,3,4-四氢异喹啉（THIQ）类似物，并通过[³H]次黄嘌呤掺入实验对疟原虫进行了体外测试。
• Catalytic Pictet–Spengler reactions using Yb(OTf)3
  作者：Kei Manabe、Daisuke Nobutou、Shū Kobayashi

  DOI：10.1016/j.bmc.2005.05.018

  日期：2005.9

  The catalytic Pictet-Spengler reactions proceeded in high yields with high regioselectivity in the presence of a catalytic amount of Yb(OTf)(3) and a dehydrating agent at room temperature. High regioselectivities were obtained in these reactions, and it is suggested that the reactions proceeded under kinetic control. (c) 2005 Elsevier Ltd. All rights reserved.