1,3-bis(4-methoxyphenyl)prop-2-en-1-oneoxime | 21067-51-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-bis(4-methoxyphenyl)prop-2-en-1-oneoxime
• 英文别名: p,p'-Dimethoxy-chalkonoxim；N-[1,3-bis(4-methoxyphenyl)prop-2-enylidene]hydroxylamine
• CAS: 21067-51-6
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: KJGJLNNNAVSNHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-methoxyphenyl)prop-2-en-1-oneoxime 在 2-碘酰基苯甲酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以73%的产率得到3,5-bis(4-methoxyphenyl)isoxazole
  参考文献：
  名称：

  邻碘氧基苯甲酸介导合成 3,5-二芳基异恶唑和异恶唑-3-羧酸

  摘要：

  摘要 报道了一种以 α,β-不饱和酮肟为原料合成 3,5-二芳基异恶唑的新型、方便、环保的方法。类似地，还报道了异恶唑羧酸的新合成。这两种方法都使用高效、环保且无毒的碘氧基苯甲酸 (IBX) 作为氧化环化试剂。简单的程序、环境友好的反应条件和无毒是该方法的优点。图形概要

  DOI：

  10.1080/00397911.2013.854916
• 作为产物：
  描述：

  4,4’-二甲氧基查耳酮 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 1,3-bis(4-methoxyphenyl)prop-2-en-1-oneoxime
  参考文献：
  名称：

  邻碘氧基苯甲酸介导合成 3,5-二芳基异恶唑和异恶唑-3-羧酸

  摘要：

  摘要 报道了一种以 α,β-不饱和酮肟为原料合成 3,5-二芳基异恶唑的新型、方便、环保的方法。类似地，还报道了异恶唑羧酸的新合成。这两种方法都使用高效、环保且无毒的碘氧基苯甲酸 (IBX) 作为氧化环化试剂。简单的程序、环境友好的反应条件和无毒是该方法的优点。图形概要

  DOI：

  10.1080/00397911.2013.854916

文献信息

• An Easy Access to Oxime Ethers by <scp>Pd‐Catalyzed</scp> C—O <scp>Cross‐Coupling</scp> of Activated Aryl Bromides with Ketoximes and Chalcone Oximes
  作者：Reeta、T. M. Rangarajan、Raj Pal Singh、R. P. Singh、Manjula Singh

  DOI：10.1002/cjoc.201900540

  日期：2020.8

  An efficient Pd‐catalyzed method for C—O cross‐coupling of ketoximes and chalcone oximes with activated aryl bromides and bromo‐chalcones has been developed. All oxime ethers were obtained in good to excellent yields by [(π‐allyl)PdCl]2/t BuXPhos (L7 ) catalyst system. TrixiePhos (L11 ) was also found to be effective for the oxime coupling. This method offers an easy and smooth coupling of chalcone

  已经开发了一种有效的钯催化的方法，用于酮肟和查尔酮肟与活化的芳基溴化物和溴代查耳酮的C-O交叉偶联。通过[（π-烯丙基）PdCl] 2 / t BuXPhos（L7）催化剂体系可以很好地获得所有肟醚。还发现TrixiePhos（L11）对于肟耦合有效。该方法提供了查耳酮肟与活化的芳基溴化物和溴查耳酮的轻松，平滑的偶联，这是以前没有探索过的。
• Novel Class of Chalcone Oxime Ethers as Potent Monoamine Oxidase-B and Acetylcholinesterase Inhibitors
  作者：Jong Min Oh、T. M. Rangarajan、Reeta Chaudhary、Rishi Pal Singh、Manjula Singh、Raj Pal Singh、Anna Rita Tondo、Nicola Gambacorta、Orazio Nicolotti、Bijo Mathew、Hoon Kim

  DOI：10.3390/molecules25102356

  日期：——

  synthesized novel chalcone oxime ethers (COEs) were evaluated for inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE). Twenty-two of the 24 COEs synthesized, except COE-17 and COE-24, had potent and/or significant selective inhibitory effects on MAO-B. COE-6 potently inhibited MAO-B with an IC50 value of 0.018 µM, which was 105, 2.3, and 1.1 times more potent than clorgyline

  评估了先前合成的新型查耳酮肟醚 (COE) 对单胺氧化酶 (MAO) 和乙酰胆碱酯酶 (AChE) 的抑制活性。除 COE-17 和 COE-24 外，合成的 24 个 COE 中有 22 个对 MAO-B 具有有效和/或显着的选择性抑制作用。COE-6 以 0.018 µM 的 IC50 值有效抑制 MAO-B，分别是氯吉林、拉扎贝胺和帕吉林（参考药物）的 105、2.3 和 1.1 倍。COE-7 和 COE-22 对 MAO-B 也有活性，两者的 IC50 值为 0.028 µM，分别比氯吉林和拉扎贝胺低 67 倍和 1.5 倍。大多数COEs对MAO-A和AChE表现出弱的抑制作用。COE-13 最有效地抑制 MAO-A (IC50 = 0.88 µM)，也显着抑制 MAO-B (IC50 = 0.13 µM)，它可以被认为是一种潜在的非选择性 MAO 抑制剂。COE-19 和 COE-22
• Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents
  作者：Yin Luo、Ran Song、Yao Li、Shuai Zhang、Zhi-Jun Liu、Jie Fu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2012.03.080

  日期：2012.5

  A series of deoxybenzoin oximes were recently reported as potent immunosuppressive agents by our group. In order to continue the original research for potential immunosuppressive agents with high efficacy and low toxicity, we synthesized a series of new chalcone oximes and evaluated them for their cytotoxicities and immunosuppressive activities. Among the synthesized compounds, chalcone oximes 25 and 27 exhibited lower cytotoxicities and higher inhibitory activities on anti-CD3/anti-CD28 co-stimulated lymph node cells than other compounds. Specially, compound 27 displayed 200-fold lower cytotoxicity (CC50 = 2174.39 mu M) than cyclosporin A (CC50 = 10.10 mu M) and showed SI value (SI = 176.69) close to cyclosporin A (SI = 154.13). Besides, the preliminary mechanism of inhibition effect of compounds 25 and 27 was also detected by flow cytometry, and the compounds exerted immunosuppressive activities via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Also, the deep mechanism of apoptosis was detected by Western blot analysis. (C) 2012 Elsevier Ltd. All rights reserved.
• <i>o</i>-Iodoxy Benzoic Acid–Mediated Synthesis of 3,5-Diarylisoxazoles and Isoxazole-3-carboxylic Acids
  作者：Vidya G. Desai、Sneha R. Naik、Kashinath L. Dhumaskar

  DOI：10.1080/00397911.2013.854916

  日期：2014.5.19

  Abstract A new, convenient, ecofriendly synthesis of 3,5-diarylisoxazoles is reported from α,β-unsaturated ketoximes. Similarly, a novel synthesis of isoxazole carboxylic acids is also reported. Both the methods use efficient, environmentally friendly, and nontoxic iodoxybenzoic acid (IBX) as an oxidative cyclizing reagent. Easy procedure, environmentally benign reaction conditions, and nontoxicity

  摘要 报道了一种以 α,β-不饱和酮肟为原料合成 3,5-二芳基异恶唑的新型、方便、环保的方法。类似地，还报道了异恶唑羧酸的新合成。这两种方法都使用高效、环保且无毒的碘氧基苯甲酸 (IBX) 作为氧化环化试剂。简单的程序、环境友好的反应条件和无毒是该方法的优点。图形概要