6,7-dimethoxy-1-p-tolylisoquinoline | 1239326-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,7-dimethoxy-1-p-tolylisoquinoline
• 英文别名: 6,7-Dimethoxy-1-(4-methylphenyl)isoquinoline
• CAS: 1239326-24-9
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: ZQSRGLJCBWCGCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 6,7-dimethoxy-1-p-tolylisoquinoline 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium acetate 、 zinc dibromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以80%的产率得到(2-(6,7-dimethoxyisoquinolin-1-yl)-5-methylphenyl)methanol
  参考文献：
  名称：

  Ru(II)-Catalyzed Regioselective Hydroxymethylation of β-Carbolines and Isoquinolines via C–H Functionalization: Probing the Mechanism by Online ESI-MS/MS Screening

  摘要：

  A Ru(II)-catalyzed regioselective C-H activation toward hydroxymethylation of beta-carbolines and isoquinolines as effective directing groups has been developed, and the mechanism was probed by using online electrospray ionization-tandem mass spectrometry. The introduction of the hydroxymethyl group in the biologically relevant molecules routed via C-H functionalization remains an important task. Gratifyingly, this protocol draws attention to the regioselective formation of monohydroxymethylated beta-carboline/isoquinoline products exclusively.

  DOI：

  10.1021/acs.joc.9b00454
• 作为产物：
  描述：

  对甲基苯甲醛 、 3,4-二甲氧基苯乙胺 在 三氟乙酸 、 palladium 10% on activated carbon 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以78%的产率得到6,7-dimethoxy-1-p-tolylisoquinoline
  参考文献：
  名称：

  取代异喹啉文库制备的策略和综合方法

  摘要：

  开发和探索了取代异喹啉文库的生产策略。涉及Bischler-Napieralski或Pictet-Spengler反应的微波辅助变体的途径可实现取代的β-芳基乙胺衍生物的环化。然后可以将由此产生的二氢异喹啉和四氢异喹啉氧化为它们相应的异喹啉类似物。然而，另一种涉及制备和激活异喹啉-1（2 H）-ones的策略被证明是一种更实用，快速，有效的通往C1和C4取代异喹啉文库的途径。

  DOI：

  10.1021/jo100980p

文献信息

• Ru(<scp>ii</scp>)-Catalyzed regioselective carbene insertion into β-carbolines and isoquinolines
  作者：Stephy Elza John、Darshana Bora、Nagula Shankaraiah

  DOI：10.1039/d2ob00946c

  日期：——

  protocol for carbene insertion into the inert C(sp2)–H bond has been established wherein β-carbolines and isoquinolines are explored as intrinsic directing groups. The Ru(II)-catalyzed strategy employing sulfoxonium ylides as the carbene precursor offers an effective and atom-economical functionalization of substrates of biological interest with only DMSO as the sole by-product. The strategy is scalable

  已经建立了将卡宾插入惰性 C(sp 2 )-H 键的方案，其中探索了 β-咔啉和异喹啉作为内在导向基团。汝（二)-催化策略使用氧化鎓叶立德作为卡宾前体，提供了对生物感兴趣的底物的有效且原子经济的功能化，仅 DMSO 作为唯一的副产物。该策略可扩展到克级，并且还展示了广泛的官能团耐受性。ESI-MS 研究有助于识别中间体和巩固可能的机制途径。此外，研究表明，功能化分子不仅对癌细胞系表现出选择性抑制作用，而且还表现出有前景的光物理特性。
• Rh(III)-catalysed site-selective alkylation of β-carbolines/isoquinolines and tandem C H/C N functionalization to construct indolizine-indole frameworks
  作者：Darshana Bora、Stephy Elza John、Mary Sravani Galla、Manda Sathish、Nagula Shankaraiah

  DOI：10.1016/j.mcat.2022.112783

  日期：2022.12

  tolerance exploiting directing properties of pyridinic nitrogen. In this protocol, diazo compounds of diethyl malonate, dimethyl dimedone and oxindole are tested as carbene source with the release of environmentally benign N2 gas as the by-product. Moreover, to perceive mechanistic insights, ESI-MS studies were conducted, and the key intermediates associated with this transformation were identified. In

  开发了铑催化的邻位选择性卡宾插入策略以激活β-咔啉和异喹啉支架的非酸性 sp 2 C H 键。这种转变利用吡啶氮的导向特性，使 C C 键的制造具有高原子经济性、良好的产率和广泛的官能团耐受性。在该协议中，丙二酸二乙酯、二甲基二甲酮和羟吲哚的重氮化合物作为卡宾源进行了测试，释放了对环境无害的 N 2气体作为副产品。此外，为了了解机理，进行了 ESI-MS 研究，并确定了与这种转变相关的关键中间体。此外，由合成的产物完成了平面多环中氮茚-吲哚骨架的无金属结构。此外，还确定了 C N 环状化合物的肿瘤和荧光特性。
• Ru(II)-Catalyzed Regioselective Hydroxymethylation of β-Carbolines and Isoquinolines via C–H Functionalization: Probing the Mechanism by Online ESI-MS/MS Screening
  作者：Ramya Tokala、Darshana Bora、Sravani Sana、Fabiane M. Nachtigall、Leonardo S. Santos、Nagula Shankaraiah

  DOI：10.1021/acs.joc.9b00454

  日期：2019.5.3

  A Ru(II)-catalyzed regioselective C-H activation toward hydroxymethylation of beta-carbolines and isoquinolines as effective directing groups has been developed, and the mechanism was probed by using online electrospray ionization-tandem mass spectrometry. The introduction of the hydroxymethyl group in the biologically relevant molecules routed via C-H functionalization remains an important task. Gratifyingly, this protocol draws attention to the regioselective formation of monohydroxymethylated beta-carboline/isoquinoline products exclusively.
• Strategies and Synthetic Methods Directed Toward the Preparation of Libraries of Substituted Isoquinolines
  作者：Emelia Awuah、Alfredo Capretta

  DOI：10.1021/jo100980p

  日期：2010.8.20

  Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler−Napieralski or Pictet−Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues

  开发和探索了取代异喹啉文库的生产策略。涉及Bischler-Napieralski或Pictet-Spengler反应的微波辅助变体的途径可实现取代的β-芳基乙胺衍生物的环化。然后可以将由此产生的二氢异喹啉和四氢异喹啉氧化为它们相应的异喹啉类似物。然而，另一种涉及制备和激活异喹啉-1（2 H）-ones的策略被证明是一种更实用，快速，有效的通往C1和C4取代异喹啉文库的途径。