4-(3,4-dihydroisoquinolin-2(1H)-yl)phenol | 78317-86-9

• 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: 4-(3,4-dihydroisoquinolin-2(1H)-yl)phenol
• 英文别名: 1,2,3,4-tetrahydro-2-(4-hydroxyphenyl)isoquinoline；4-(3,4-dihydro-1H-isoquinolin-2-yl)phenol
• CAS: 78317-86-9
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: YJANRDANRAMKJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3,4-dihydroisoquinolin-2(1H)-yl)phenol 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 2-(4-hydroxylphenyl)-3,4-dihydroisoquinolin-2-ium bromide
  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 4-(3,4-dihydroisoquinolin-2(1H)-yl)phenol
  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。
• Solvent-driven C(sp³)–H thiocarbonylation of benzylamine derivatives under catalyst-free conditions
  作者：Jingwei Zhou、Songping Wang、Yaoming Lu、Lamei Li、Wentao Duan、Qi Wang、Hong Wang、Wentao Wei

  DOI：10.1039/d0gc03832f

  日期：——

  (QM) computations and well-designed experiments on the reaction mechanism revealed that this thiocarbonylation depends on the specific solvent that initially drives this reaction through the intermolecular hydrogen atom transfer (HAT). And the following single electron transfer (SET) induces the electron-catalyzed C–S bond formation and intramolecular HAT realizing the final establishment of the CS bond

  由于硫代羰基（C S键）的特殊性，仅开发了有限的C（sp 3）–H硫代羰基化方法，特别是有效而方便的方法，用于合成硫代酰胺。受“基于溶剂特定性”设计策略的启发，我们发现了一种简单，实用且环保的C（sp 3）–H苄胺底物的硫羰基化反应，可在无催化剂条件下轻松合成硫酰胺。这种无催化剂的硫代羰基化作用可耐受各种各样的苄胺衍生物。此外，对反应机理的（QM）计算和精心设计的实验表明，这种硫羰基化取决于特定的溶剂，该溶剂最初通过分子间氢原子转移（HAT）驱动该反应。随后的单电子转移（SET）诱导了电子催化的C–S键的形成和分子内HAT，最终实现了C S键的建立。
• The use of 2-phenyltetralin derivatives, or heterocyclic analogues, in medicine and pharmaceutical compositions containing them
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0025598A1

  公开（公告）日：1981-03-25

  Known and novel compounds of formula (i) wherein E is a sulphur atom or a NH or CH2 group, J is a nitrogen atom or a CH group, Q is a sulphur atom or a NR3 or CHR3 group, Z is oxygen or sulphur atom or a NR4 or CHR4 group and R' represents four substituents and R2 represents five substituents, provided at least three of E, J, Q, and Z are methylene residues, are active against viruses, especially rhinoviruses. Methods for producing the compounds are described, as are pharmaceutical formulations and methods for administering the compounds to cure or prevent rhinoviral infections.

  已知和新型的式(i)化合物 其中 E 是硫原子或 NH 或 CH2 基团，J 是氮原子或 CH 基团，Q 是硫原子或 NR3 或 CHR3 基团，Z 是氧或硫原子或 NR4 或 CHR4 基团，R'代表四个取代基，R2 代表五个取代基，条件是 E、J、Q 和 Z 中至少有三个是亚甲基残基。本文介绍了生产这些化合物的方法，以及使用这些化合物治疗或预防鼻病毒感染的药物制剂和方法。
• US4801593A
  申请人：——

  公开号：US4801593A

  公开（公告）日：1989-01-31
• 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。