6,7-dimethoxy-1-(o-tolyl)-1,2,3,4-tetrahydroisoquinoline | 55580-56-8

• 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: 6,7-dimethoxy-1-(o-tolyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1,2,3,4-tetrahydro-6,7-dimethoxy-1-(2-methylphenyl)isoquinoline；6,7-Dimethoxy-1-(2-methylphenyl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 55580-56-8
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: FWNSCGHIPGMTSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-1-(o-tolyl)-1,2,3,4-tetrahydroisoquinoline 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 以35%的产率得到
  参考文献：
  名称：

  6-氧代异吗啡和四氢异喹啉衍生物的新方法

  摘要：

  2,3-二氢-6-羟基-5-甲氧基-7- ħ -二苯并[德，ħ ]喹啉-7-酮，6-羟基-5-甲氧基-7- ħ -二苯并[德，ħ ]喹啉-7-一和2-（6,7-二甲氧基-3,4-二氢异喹啉-1-基）苯甲酸苄酯（可通过Bischler-Napieralski环化轻松获得）用作起始原料，可制得6-氧代异吗啡和2,3-二甲氧基‐5,6,8,12b-四氢异吲哚并[1,2- a ]异喹啉为主要产品。但是，在温和条件下苯甲酸苄酯衍生物的催化加氢提供了1,2,3,4-四氢-6,7-二甲氧基-1-（2-甲基苯基）异喹啉。

  DOI：

  10.1002/hlca.200900394
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 4.0h， 生成 6,7-dimethoxy-1-(o-tolyl)-1,2,3,4-tetrahydroisoquinoline
  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

• Hybrid Catalysis Enabling Room-Temperature Hydrogen Gas Release from <i>N</i>-Heterocycles and Tetrahydronaphthalenes
  作者：Shota Kato、Yutaka Saga、Masahiro Kojima、Hiromu Fuse、Shigeki Matsunaga、Arisa Fukatsu、Mio Kondo、Shigeyuki Masaoka、Motomu Kanai

  DOI：10.1021/jacs.7b00253

  日期：2017.2.15

  Hybrid catalyst systems to achieve acceptorless dehydrogenation of N-heterocycles and tetrahydronaphthalenes-model substrates for liquid organic hydrogen carriers-were developed. A binary hybrid catalysis comprising an acridinium photoredox catalyst and a Pd metal catalyst was effective for the dehydrogenation of N-heterocycles, whereas a ternary hybrid catalysis comprising an acridinium photoredox

  开发了用于实现 N-杂环和四氢萘模型基质的无受体脱氢的混合催化剂系统，用于液态有机氢载体。包含吖啶光氧化还原催化剂和 Pd 金属催化剂的二元杂化催化对 N-杂环的脱氢有效，而包含吖啶光氧化还原催化剂、Pd 金属催化剂和硫代磷酰亚胺有机催化剂的三元杂化催化实现了四氢萘的脱氢。这些混合催化剂体系允许在温和条件下，即室温下的可见光照射，从六元N-杂环和四氢萘中释放2摩尔当量的H 2 气体。两种或三种不同催化剂类型的组合使用对于催化活性至关重要。
• US4001244A
  申请人：——

  公开号：US4001244A

  公开（公告）日：1977-01-04
• 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.
• New Approaches to 6-Oxoisoaporphine and Tetrahydroisoquinoline Derivatives
  作者：Eduardo Sobarzo-Sánchez、Eugenio Uriarte、Lourdes Santana、Ricardo A. Tapia、Paulo Pérez Lourido

  DOI：10.1002/hlca.200900394

  日期：——

  starting materials to afford 6‐oxoisoaporphine and 2,3‐dimethoxy‐5,6,8,12b‐tetrahydroisoindolo[1,2‐a]isoquinoline as the main products. However, the catalytic hydrogenation of the benzyl benzoate derivative afforded, under mild conditions, 1,2,3,4‐tetrahydro‐6,7‐dimethoxy‐1‐(2‐methylphenyl)isoquinoline.

  2,3-二氢-6-羟基-5-甲氧基-7- ħ -二苯并[德，ħ ]喹啉-7-酮，6-羟基-5-甲氧基-7- ħ -二苯并[德，ħ ]喹啉-7-一和2-（6,7-二甲氧基-3,4-二氢异喹啉-1-基）苯甲酸苄酯（可通过Bischler-Napieralski环化轻松获得）用作起始原料，可制得6-氧代异吗啡和2,3-二甲氧基‐5,6,8,12b-四氢异吲哚并[1,2- a ]异喹啉为主要产品。但是，在温和条件下苯甲酸苄酯衍生物的催化加氢提供了1,2,3,4-四氢-6,7-二甲氧基-1-（2-甲基苯基）异喹啉。