N-(4-methoxyphenyl)quinazolin-4-amine | 34932-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(4-methoxyphenyl)quinazolin-4-amine
• CAS: 34932-32-6
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: NSUJCDDALMMGFW-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  418.4±30.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-(1,2-乙炔二基)二(4-甲基苯) 、 N-(4-methoxyphenyl)quinazolin-4-amine 在 四丁基溴化铵 、 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以61%的产率得到4-(5-methoxy-2,3-di-p-tolyl-1H-indol-1-yl)quinazoline
  参考文献：
  名称：

  Catalyst and solvent switched divergent C–H functionalization: oxidative annulation of N-aryl substituted quinazolin-4-amine with alkynes

  摘要：

  催化剂和溶剂控制的N-芳基取代的喹唑啉-4-胺与内部炔烃的C-H键的ortho/peri位选择性氧化环化。

  DOI：

  10.1039/d0ob00318b
• 作为产物：
  描述：

  4-羟基喹唑啉 在 六氯环三磷腈 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 N-(4-methoxyphenyl)quinazolin-4-amine
  参考文献：
  名称：

  An efficient HCCP-mediated direct amination of quinazolin-4(3H)-ones

  摘要：

  An efficient direct amination of quinazolin-4(3H)-ones has been developed. Treatment of quinazolin-4(3H)-ones with HCCP, DIPEA, and N-contained nucleophiles in acetonitrile could be able to form the corresponding 4-aminoquinazoline derivatives. Under the optimal reaction conditions, the amination products were achieved in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.067

文献信息

• Amination of Heteroaryl Chlorides: Palladium Catalysis or S_NAr in Green Solvents?
  作者：Katie Walsh、Helen F. Sneddon、Christopher J. Moody

  DOI：10.1002/cssc.201300239

  日期：2013.8

  reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile SNAr reaction and N‐arylation. The reaction is less satisfactory with pyridines unless an additional electron‐withdrawing group is present. The results showed that the transition‐metal‐free SNAr reaction not only compares favourably to palladium‐catalysed

  嘧啶、吡嗪和喹唑啉系列中的杂芳基氯化物与水中的胺在 KF 存在下发生反应，导致容易的 S N Ar 反应和N芳基化。除非存在额外的吸电子基团，否则吡啶的反应不太令人满意。结果表明，无过渡金属的 S N Ar 反应不仅优于钯催化的偶联反应，而且在碱和溶剂方面也可以在环境可接受的（“绿色”）条件下进行。
• Synthesis of Fused Polycyclic 4‐Anilinoquinazolines and <i>N</i> ‐Quinazoline‐Indoles <i>via</i> Selective C−H Bond Activation
  作者：Xin‐Yang Liu、Hao Liu、Xian‐Zhang Liao、Lin Dong、Fen‐Er Chen

  DOI：10.1002/adsc.202000895

  日期：2020.12.22

  An efficient rhodium(III)‐catalyzed site‐selective functionalization of 4‐anilinoquinazolines offers exciting possibilities for fused polycyclic 4‐anilinoquinazoline derivatives and N‐quinazoline‐indoles by using diazo compounds as the elegant coupling partners. This one‐pot cascade approach to establish various complex 4‐anilinoquinazoline units with potential biological activities only depends on

  通过使用重氮化合物作为优雅的偶联伙伴，高效的铑（III）催化4-苯胺基喹唑啉的位点选择性官能化为稠合多环4-苯胺基喹唑啉衍生物和N-喹唑啉吲哚提供了令人兴奋的可能性。这种单罐级联方法可以建立具有潜在生物活性的各种复杂的4-苯胺基喹唑啉单元，仅取决于底物和添加剂。
• Cu/<i>N</i>,<i>N</i>′-Dibenzyloxalamide-Catalyzed <i>N</i>-Arylation of Heteroanilines
  作者：Zhixiang Chen、Dawei Ma

  DOI：10.1021/acs.orglett.9b02509

  日期：2019.9.6

  N,N'-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol % CuBr and 10 mol % DBO. For (hetero)aryl bromides/iodides, coupling reaction took place at 80-100 °C with 1 mol % CuI and 2 mol % DBO. A variety of heteroanilines worked well

  N，N'-二苄基草酰胺（DBO）被确定为一种强大的配体，用于促进Cu催化杂苯胺与（杂）芳基卤化物的偶联。对于（杂）芳基氯，偶联反应在130℃下与5mol％的CuBr和10mol％的DBO发生。对于（杂）芳基溴化物/碘化物，偶合反应在80-100°C下与1 mol％的CuI和2 mol％的DBO进行。各种杂苯胺效果很好，以高到极高的收率提供了芳基化产物。
• Compounds that enhance Atoh-1 expression
  申请人：MASSACHUSETTS EYE & EAR INFIRMARY

  公开号：EP2732819A2

  公开（公告）日：2014-05-21

  This invention generally provides compounds, pharmaceutical compositions, and methods for their use, which include methods that result in increased expression in an Atoh1 gene (e.g., Hath1) in a biological cell. More specifically, the invention relates to the treatment of diseases and/or disorders that would benefit from increased Atoh1 expression, e.g. a hearing impairment or imbalance disorder associated with a loss of auditory hair cells, or a disorder associated with abnormal cellular proliferation.

  本发明一般提供化合物、药物组合物及其使用方法，其中包括导致生物细胞中 Atoh1 基因（如 Hath1）表达增加的方法。更具体地说，本发明涉及可从 Atoh1 表达增加中获益的疾病和/或失调症的治疗，例如与听觉毛细胞丧失有关的听力损伤或失调症，或与细胞异常增殖有关的失调症。
• Compounds that enhance Atoh1 expression
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：US10406163B2

  公开（公告）日：2019-09-10

  This invention generally provides compounds, pharmaceutical compositions, and methods for their use, which include methods that result in increased expression in an Atoh1 gene (e.g., Hath1) in a biological cell. More specifically, the invention relates to the treatment of diseases and/or disorders that would benefit from increased Atoh1 expression, e.g., a hearing impairment or imbalance disorder associated with a loss of auditory hair cells, or a disorder associated with abnormal cellular proliferation.

  本发明一般提供化合物、药物组合物及其使用方法，其中包括导致生物细胞中Atoh1基因（如Hath1）表达增加的方法。更具体地说，本发明涉及可从 Atoh1 表达增加中获益的疾病和/或失调症的治疗，例如，与听觉毛细胞丧失有关的听力损伤或失调症，或与细胞异常增殖有关的失调症。