5-bromo-N-(quinolin-8-yl)thiophene-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-bromo-N-(quinolin-8-yl)thiophene-2-carboxamide
• 英文别名: 5-bromo-N-quinolin-8-ylthiophene-2-carboxamide
• 化学式: C₁₄H₉BrN₂OS
• mdl: MFCD10642657
• 分子量: 333.208
• InChiKey: HTUHTYNBZOOHPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-N-(quinolin-8-yl)thiophene-2-carboxamide 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 sodium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.3h， 生成 5-phenyl-N-(quinolin-8-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  One-Pot Approach to N-Quinolyl 3′/4′-Biaryl Carboxamides by Microwave-Assisted Suzuki–Miyaura Coupling and N-Boc Deprotection

  摘要：

  N-Quinolyl biaryl carboxamides have received tremendous attention for their notable biological properties. Here we have described a general protocol for the preparation of N-quinolyl 3'/4'-biaryl carboxamides by microwave-assisted Suzuki-Miyaura cross-coupling reaction and N-Boc deprotection in one pot. This method, which did not require acids, was used to produce a series of N-quinolyl 3'/4'-biaryl carboxamides with excellent functional group tolerance and high yields (70% to 95%).

  DOI：

  10.1021/acs.joc.6b01725
• 作为产物：
  描述：

  6-氨基喹啉 、 5-溴-2-羧基噻吩 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 5-bromo-N-(quinolin-8-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  QUINOLINES THAT MODULATE SERCA AND THEIR USE FOR TREATING DISEASE

  摘要：

  本文提供了喹啉，例如Formula I的化合物，其药物组合物，以及用于治疗、预防或缓解神经疾病、神经退行性疾病或糖尿病的一种或多种症状的方法。本文还提供了用于调节肌浆网/内质网C2+ATP酶活性的方法。

  公开号：

  US20190151303A1

文献信息

• Copper-Catalyzed C–H Carbamoyloxylation of Aryl Carboxamides with CO₂ and Amines at Ambient Conditions
  作者：Xiang Luo、Xianheng Song、Wenfang Xiong、Jianheng Li、Mingkang Li、Zefeng Zhu、Shuxian Wei、Albert S. C. Chan、Yong Zou

  DOI：10.1021/acs.orglett.9b00122

  日期：2019.4.5

  A copper-catalyzed, 8-aminoquinoline-assisted, one-pot three-component coupling of aryl carboxamides, CO2, and amines has been developed. This protocol proceeds smoothly in the presence of inexpensive CuI and MnO2 at room temperature under atmospheric CO2 pressure, leading to simultaneous construction of C–O and C–N bonds. The reaction displays a broad substrate scope, high functional group tolerance

  已经开发了铜催化的8-氨基喹啉辅助的一锅三组分芳基羧酰胺，CO 2和胺的偶联。在室温下，在大气CO 2压力下，存在廉价的CuI和MnO 2的情况下，该方案可以顺利进行，从而可以同时构建C-O和C-N键。该反应显示出宽的底物范围，高的官能团耐受性和优异的单选择性，为合成各种O-芳基氨基甲酸酯提供了操作上简单的方法。
• Cobalt-Catalyzed Oxidative C−H/C−H Cross-Coupling between Two Heteroarenes
  作者：Guangying Tan、Shuang He、Xiaolei Huang、Xingrong Liao、Yangyang Cheng、Jingsong You

  DOI：10.1002/anie.201604580

  日期：2016.8.22

  cross‐coupling between two heteroarenes is reported, which exhibits a broad substrate scope and a high tolerance level for sensitive functional groups. When the amount of Co(OAc)2⋅4 H2O is reduced from 6.0 to 0.5 mol %, an excellent yield is still obtained at an elevated temperature with a prolonged reaction time. The method can be extended to the reaction between an arene and a heteroarene. It is worth noting

  报道了两个杂芳烃之间钴催化的氧化C / H / C-H交叉偶联的第一个例子，它显示出较宽的底物范围和对敏感官能团的高耐受性水平。当（OAC）Co量2 ⋅4ħ 2 O的6.0〜0.5摩尔％降低，仍然是在升高的温度下用延长反应时间得到良好的产率。该方法可以扩展到芳烃和杂芳烃之间的反应。值得注意的是，Ag 2 CO 3氧化剂是可再生的。通过自由基俘获实验，氢/氘交换实验，动力学同位素效应，电子顺磁共振（EPR）和高分辨率质谱（HRMS）进行的初步机理研究表明，单个电子转移（SET）路径是有效的，这是截然不同的通常从两个杂芳烃之间经过充分描述的氧化性C / H / C交叉偶联反应通过双C-H键激活途径进行。
• Nickel Catalysis Enables Oxidative C(sp² )-H/C(sp² )-H Cross-Coupling Reactions between Two Heteroarenes
  作者：Yangyang Cheng、Yimin Wu、Guangyin Tan、Jingsong You

  DOI：10.1002/anie.201606529

  日期：2016.9.26

  Nickel can be used to promote oxidative C(sp2)−H/C(sp2)−H cross‐coupling between two heteroarenes. The reaction scope can be extended to aromatic carboxamides as the coupling partner. The reaction exhibits high functional‐group compatibility and broad substrate scope. The silver oxidant can be recycled to reduce costs and waste, which is very useful for practical applications.

  镍可用于促进两个杂芳烃之间的氧化C（sp 2）-H / C（sp 2）-H交叉偶联。反应范围可扩展至芳族羧酰胺作为偶联伴侣。该反应具有很高的官能团相容性和广泛的底物范围。可以循环使用银氧化剂以减少成本和浪费，这对于实际应用非常有用。
• [EN] QUINOLINES AND THEIR USE FOR TREATING ENDOPLASMIC RETICULUM STRESS-CAUSED DISEASES<br/>[FR] QUINOLÉINES ET LEUR UTILISATION POUR TRAITER LES MALADIES DUES AU STRESS DU RÉTICULUM ENDOPLASMIQUE
  申请人：CELLADON CORP

  公开号：WO2016032569A1

  公开（公告）日：2016-03-03

  Provided herein are quinolines, e.g., a compound of Formula (I) or (IB), pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of an endoplasmic reticulum stress-caused disease. Also provided herein are methods of their use for reducing endoplasmic reticulum stress and modulating the activity of a sarcoplasmic/endoplasmic reticulum Ca2+ ATPase.

  本文提供了喹啉类化合物，例如，化合物的化学式为（I）或（IB），以及其药物组合物，并用于治疗、预防或改善内质网应激引起的一种或多种疾病症状的方法。本文还提供了用于减少内质网应激并调节肌浆/内质网Ca2+ ATP酶活性的方法。
• QUINOLINES AND THEIR USE FOR TREATING ENDOPLASMIC RETICULUM STRESS-CAUSED DISEASES
  申请人：EIGER BIOPHARMACEUTICALS, INC.

  公开号：US20170281611A1

  公开（公告）日：2017-10-05

  Provided herein are quinolines, e.g., a compound of Formula (I) or (IB), pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of an endoplasmic reticulum stress-caused disease. Also provided herein are methods of their use for reducing endoplasmic reticulum stress and modulating the activity of a sarcoplasmic/endoplasmic reticulum Ca 2+ ATPase.