2-(2-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline | 1057280-08-6

• 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: 2-(2-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-((o-trifluoromethyl)-phenyl)-1,2,3,4-tetrahidroisoquinoline；2-[2-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline
• CAS: 1057280-08-6
• 化学式: C₁₆H₁₄F₃N
• 分子量: 277.289
• InChiKey: DZNORFARCOSRCU-UHFFFAOYSA-N

物化性质

• 沸点：
  361.6±42.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 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：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline 在 copper(II) choride dihydrate 、 氢溴酸 、 氧气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis of 2-Aryl-3,4-dihydroisoquinolin-2-ium Bromides and Their <i>in Vitro</i> Acaricidal Activity against <i>Psoroptes cuniculi</i>

  摘要：

  通过使用天然活性季铵类异喹啉生物碱——血根碱（sanguinarine）作为模型分子，设计合成了一系列结构简单的季铵类2-芳基-3,4-二氢异喹啉-2-锗化合物，并评估了其对兔毛滴虫（P. cuniculi）的体外杀螨活性。开发了一种以异喹啉为起始材料的新方法。结果显示，在24个测试化合物中，有22个在0.4 mg/mL浓度下显示出不同程度的活性。14个化合物的效果显著优于标准杀螨剂伊维菌素（ivermectin）和血根碱的衍生物6-甲氧基二氢血根碱（6-methoxy dihydrosanguinarine）（p<0.05）。它们的综合相对活性是伊维菌素的1.4到16.5倍，6-甲氧基二氢血根碱的1.5到18.8倍。结构-活性关系表明，在N-苯环上引入取代基，尤其是卤素原子和三氟甲基基团，会显著提高活性。氟原子、甲基和羟基的位置对活性也有非常显著的影响。结论是，2-芳基-3,4-二氢异喹啉-2-锗化合物是开发新型异喹啉杀螨剂的有前景的候选者。

  DOI：

  10.1248/cpb.c12-00876
• 作为产物：
  描述：

  异色满 在 氢碘酸 、 sodium dodecyl-sulfate 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-(2-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis of 2-Aryl-3,4-dihydroisoquinolin-2-ium Bromides and Their <i>in Vitro</i> Acaricidal Activity against <i>Psoroptes cuniculi</i>

  摘要：

  通过使用天然活性季铵类异喹啉生物碱——血根碱（sanguinarine）作为模型分子，设计合成了一系列结构简单的季铵类2-芳基-3,4-二氢异喹啉-2-锗化合物，并评估了其对兔毛滴虫（P. cuniculi）的体外杀螨活性。开发了一种以异喹啉为起始材料的新方法。结果显示，在24个测试化合物中，有22个在0.4 mg/mL浓度下显示出不同程度的活性。14个化合物的效果显著优于标准杀螨剂伊维菌素（ivermectin）和血根碱的衍生物6-甲氧基二氢血根碱（6-methoxy dihydrosanguinarine）（p<0.05）。它们的综合相对活性是伊维菌素的1.4到16.5倍，6-甲氧基二氢血根碱的1.5到18.8倍。结构-活性关系表明，在N-苯环上引入取代基，尤其是卤素原子和三氟甲基基团，会显著提高活性。氟原子、甲基和羟基的位置对活性也有非常显著的影响。结论是，2-芳基-3,4-二氢异喹啉-2-锗化合物是开发新型异喹啉杀螨剂的有前景的候选者。

  DOI：

  10.1248/cpb.c12-00876

文献信息

• 2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships
  作者：Zhe Hou、Rui Yang、Cen Zhang、Li-Fei Zhu、Fang Miao、Xin-Juan Yang、Le Zhou

  DOI：10.3390/molecules180910413

  日期：——

  The title compounds are a class of structurally simple analogues of quaternary benzo[c]phenanthridine alkaloids (QBAs). In order to develop novel QBA-like antifungal drugs, in this study, 24 of the title compounds with various substituents on the N-phenyl ring were evaluated for bioactivity against seven phytopathogenic fungi using the mycelial growth rate method and their SAR discussed. Almost all the compounds showed definite activities in vitro against each of the test fungi at 50 μg/mL and a broad antifungal spectrum. In most cases, the mono-halogenated compounds 2–12 exhibited excellent activities superior to the QBAs sanguinarine and chelerythrine. Compound 8 possessed the strongest activities on each of the fungi with EC50 values of 8.88–19.88 µg/mL and a significant concentration-dependent relationship. The SAR is as follows: the N-phenyl group is a high sensitive structural moiety for the activity and the characteristics and position of substituents intensively influence the activity. Generally, electron-withdrawing substituents remarkably enhance the activity while electron-donating substituents cause a decrease of the activity. In most cases, ortha- and para-halogenated isomers were more active than the corresponding m-halogenated isomers. Thus, the title compounds emerged as promising lead compounds for the development of novel biomimetic antifungal agrochemicals. Compounds 8 and 2 should have great potential as new broad spectrum antifungal agents for plant protection.

  标题化合物是一类四价苯并[c]菲啶生物碱（QBAs）的结构简单的类似物。为了开发新型的类似QBA的抗真菌药物，本研究评估了24种在N-苯基环上具有不同取代基的标题化合物，对七种植物病原真菌的生物活性进行测试，采用菌丝生长速率法，并讨论了其结构活性关系（SAR）。几乎所有化合物在50 μg/mL的浓度下，对每种测试真菌均显示出明显的体外活性，并且具有广泛的抗真菌谱。在大多数情况下，单卤化化合物2–12的活性优于QBAs中的血根碱和美根草碱。化合物8对每种真菌的活性最强，EC50值为8.88–19.88 µg/mL，且显示出显著的浓度依赖性关系。SAR如下：N-苯基基团是影响活性的高度敏感结构部分，取代基的特性和位置对活性有显著影响。通常，电子吸引取代基显著增强活性，而电子供给取代基则导致活性降低。在大多数情况下，邻位和对位卤化异构体的活性高于相应的间位卤化异构体。因此，标题化合物被认为是开发新型仿生抗真菌农药的有希望的先导化合物。化合物8和2在植物保护作为新的广谱抗真菌剂方面具有很大的潜力。
• Visible-light promoted photocatalyst-free aerobic α-oxidation of tertiary amines to amides
  作者：Xinpeng Xie、Xuan Guo、Kaikai Qiao、Lei Shi

  DOI：10.1039/d2ob01565j

  日期：——

  strategy for the α-oxygenation of tertiary amines by molecular oxygen (1 atm), enabled by electron–donor–acceptor (EDA) complexes, has been developed. This EDA-complex mediated process provides a facile access to amides and esters from readily accessible corresponding amines and ethers without the need for an external photoredox catalyst, and also features mild reaction conditions, broad substrate scope

  已经开发了一种无光催化剂、可见光诱导的叔胺通过分子氧（1 atm）氧化的策略，该策略由电子-供体-受体（EDA）配合物实现。这种 EDA 复合物介导的工艺无需外部光氧化还原催化剂即可从容易获得的相应胺和醚中轻松获得酰胺和酯，并且还具有温和的反应条件、广泛的底物范围和出色的官能团兼容性。机理研究表明，EDA 配合物在可见光照射下的分解引发了短自由基链式反应。
• Oxidative α-Functionalization of 1,2,3,4-Tetrahydroisoquinolines Catalyzed by a Magnetically Recoverable Copper Nanocatalyst. Application in the Aza-Henry Reaction and the Synthesis of 3,4-Dihydroisoquinolones
  作者：Esteban E. Bjerg、Joaquín Marchán-García、Eduardo Buxaderas、Yanina Moglie、Gabriel Radivoy

  DOI：10.1021/acs.joc.2c01782

  日期：2022.10.21

  consisting of copper nanoparticles immobilized on silica-coated maghemite (CuNPs/MagSilica) has been accomplished. The methodology was successfully applied in the cross-dehydrogenative coupling (CDC) reaction of N-aryl THIQs and other tertiary amines with nitromethane as a pro-nucleophile (aza-Henry reaction) and the α-oxidation of THIQs with O2 as a green oxidant. Phosphite, alkyne, or indole derivatives

  由固定在二氧化硅包覆的磁赤铁矿 (CuNPs/MagSilica) 上的铜纳米粒子组成的多功能多相纳米催化剂促进了 2-芳基-1,2,3,4-四氢异喹啉 (THIQ) 的氧化 α-功能化。该方法已成功应用于N-芳基THIQs和其他叔胺与硝基甲烷作为亲核试剂（氮杂-亨利反应）的交叉脱氢偶联（CDC）反应以及THIQs与O 2的α-氧化作为绿色氧化剂。亚磷酸酯、炔烃或吲哚衍生物也被证明是适合在与 THIQ 的 CDC 反应中用作亲核试剂的候选物。该催化剂具有非常低的铜载量（0.4-1.0 mol % Cu），可以通过外部磁铁轻松回收，并在四个循环中重复使用，而不会显着降低活性。
• Synthesis of 2-Aryl-3,4-dihydroisoquinolin-2-ium Bromides and Their &lt;i&gt;in Vitro&lt;/i&gt; Acaricidal Activity against &lt;i&gt;Psoroptes cuniculi&lt;/i&gt;
  作者：Yan-Ni Ma、Xin-Juan Yang、Le Pan、Zhe Hou、Hui-Ling Geng、Xiao-Ping Song、Le Zhou、Fang Miao

  DOI：10.1248/cpb.c12-00876

  日期：——

  By employing sanguinarine, a natural active quaternary isoquinoline alkaloid, as a model molecule, a series of structurally simple quaternary 2-aryl-3,4-dihydroisoquinolin-2-ium compounds were designed and synthesized and evaluated for in vitro acaricidal activity against P. cuniculi. A new approach towards the title compounds was developed with isochroman as starting material. The results showed that 22 of 24 tested compounds displayed the activity in varying degrees at 0.4 mg/mL. Fourteen compounds were significantly more effective than ivermectin, a standard acaricide, and 6-methoxy dihydrosanguinarine, a derivative of sanguinarine (p<0.05). And their comprehensive relative activity was 1.4 to 16.5 times than that of ivermectin and 1.5 to 18.8 times than that of 6-methoxy dihydrosanguinarine. The structure–activity relationship indicated that the introduction of a substituent to N-benzene ring, especially halogen atom and trifluoromethyl group, led to great improvement of the activity. The position of fluorine atom, methyl group and hydroxyl group made very significant effects on the activity. It was concluded that 2-aryl-3,4-dihydroisoquinolin-2-iums are very promising candidates for the development of new isoquinoline acaricidal agents.

  通过使用天然活性季铵类异喹啉生物碱——血根碱（sanguinarine）作为模型分子，设计合成了一系列结构简单的季铵类2-芳基-3,4-二氢异喹啉-2-锗化合物，并评估了其对兔毛滴虫（P. cuniculi）的体外杀螨活性。开发了一种以异喹啉为起始材料的新方法。结果显示，在24个测试化合物中，有22个在0.4 mg/mL浓度下显示出不同程度的活性。14个化合物的效果显著优于标准杀螨剂伊维菌素（ivermectin）和血根碱的衍生物6-甲氧基二氢血根碱（6-methoxy dihydrosanguinarine）（p<0.05）。它们的综合相对活性是伊维菌素的1.4到16.5倍，6-甲氧基二氢血根碱的1.5到18.8倍。结构-活性关系表明，在N-苯环上引入取代基，尤其是卤素原子和三氟甲基基团，会显著提高活性。氟原子、甲基和羟基的位置对活性也有非常显著的影响。结论是，2-芳基-3,4-二氢异喹啉-2-锗化合物是开发新型异喹啉杀螨剂的有前景的候选者。