ethyl (E)-3-(8-hydroxyquinolin-2-yl)acrylate | 93985-78-5

• 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: ethyl (E)-3-(8-hydroxyquinolin-2-yl)acrylate
• 英文别名: Ethyl (2E)-3-(8-hydroxy-2-quinolinyl)-2-propenoate；ethyl (E)-3-(8-hydroxyquinolin-2-yl)prop-2-enoate
• CAS: 93985-78-5
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: YOHGCXFUDOOPAC-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(8-hydroxyquinolin-2-yl)acrylate 在 水 、 1-羟基苯并三唑 、 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 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Z)-4-((1-(3-(8-hydroxyquinolin-2-yl)acryloyl)piperidin-4-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Nitric oxide-donating and reactive oxygen species-responsive prochelators based on 8-hydroxyquinoline as anticancer agents

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113153
• 作为产物：
  描述：

  8-羟基喹啉-2-甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 ethyl (E)-3-(8-hydroxyquinolin-2-yl)acrylate
  参考文献：
  名称：

  WO2007/135081

  摘要：

  公开号：

文献信息

• Waste-minimized synthesis of C2 functionalized quinolines exploiting iron-catalysed C–H activation
  作者：Francesco Ferlin、Agnese Zangarelli、Simone Lilli、Stefano Santoro、Luigi Vaccaro

  DOI：10.1039/d0gc03351k

  日期：——

  Herein we present an efficient and regioselective iron-catalyzed methodology for the external oxidant-free C–H activation of quinoline N-oxide.

  本文我们介绍了一种高效且区域选择性的铁催化方法，用于无需外部氧化剂就能激活喹啉N-氧化物中的C–H键。

• Histamine Receptor Antagonists Comprising an Azepin Core
  申请人：Ancliff Rachael Ann

  公开号：US20090181950A1

  公开（公告）日：2009-07-16

  The present invention relates to compounds of formula (I), and salts thereof, processes for their preparation, to compositions containing them and to their use in the treatment of various disorders, such as allergic rhinitis.

  本发明涉及式(I)的化合物及其盐，其制备过程，包含它们的组合物，以及它们在治疗各种疾病，如过敏性鼻炎中的应用。
• Palladium-Catalyzed Alkenylation of Quinoline-<i>N</i>-oxides via C−H Activation under External-Oxidant-Free Conditions
  作者：Junliang Wu、Xiuling Cui、Lianmei Chen、Guojie Jiang、Yangjie Wu

  DOI：10.1021/ja902762a

  日期：2009.10.7

  The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27-95% yield. The catalytic process is proposed to proceed via direct C-H bond activation of the quinoline-N-oxide with Pd(OAc)(2) followed by Heck coupling with the olefin. The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(11) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants.
• Donor finger morbidity in cross-finger flaps
  作者：P Paterson、O.G Titley、J.D Nancarrow

  DOI：10.1016/s0020-1383(99)00205-3

  日期：2000.5

  We reviewed 16 patients who had cross-finger flap procedures carried out between 1991 and 1996 at the West Midlands Regional centre for Plastic and Reconstructive Surgery. We looked specifically at the donor finger morbidity of each patient with a median follow up interval of 43 months.At follow up there were 10 patients with cold intolerance, eight patients with subjective joint stiffness and a documented reduced range of finger joint movement. Skin graft reconstruction of the secondary defect was associated with poor colour match in eight cases (seven hyperpigmented, one hypopigmented) and visible contour deformity in eight cases. There were no clinically significant differences between split skin graft or full thickness skin graft for donor finger reconstruction.Although cross-finger flaps may provide soft tissue cover in a variety of finger pulp injuries, these results show an alarming incidence of donor finger morbidity associated with such procedures. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Nitric oxide-donating and reactive oxygen species-responsive prochelators based on 8-hydroxyquinoline as anticancer agents
  作者：Yuxia Zhang、Jiaxin Yang、Tingting Meng、Yajuan Qin、Tingyou Li、Junjie Fu、Jian Yin

  DOI：10.1016/j.ejmech.2021.113153

  日期：2021.2