(E)-3-(dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-one | 927829-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-(dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-one
• 英文别名: 3-(Dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-one
• CAS: 927829-32-1
• 化学式: C₁₁H₁₂FNO
• 分子量: 193.221
• InChiKey: MJEQZIDZSNCFKG-VOTSOKGWSA-N

物化性质

• 沸点：
  270.8±40.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-one 在 ammonium acetate 、 一水合肼 、 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Protective effect of novel substituted nicotine hydrazide analogues against hypoxic brain injury in neonatal rats via inhibition of caspase

  摘要：

  In hypoxic-ischemic injury of the brain of neonates, the level of caspase-3 was found to be aberrantly activated. Its overexpression leads to the alteration of cytoskeleton protein fodrin and loss of DNA repair enzyme which ultimately results in neurological impairment and disability. Concerning this, the present study was intended to develop novel nicotine hydrazide analogues as caspase inhibitors via efficient synthetic route. These compounds were subsequently tested for inhibitory activity against caspase-3 and -7 where they exhibit highly potent activity against caspase-3 revealing compound 5k as most potent inhibitor (IC50 = 19.4 +/- 2.5 mu M). In Western blot analysis, 5k considerably inhibits the overexpression of caspase-3. The aryl nicotinate of compound 5k, as indicated by molecular docking was found to engage His121 and critical enzyme thiols, i.e., Cys163 of caspase-3 for its potent activity. Moreover, histopathological examination of brain tissues and hippocampus neurons showed that compound 5k considerably improves the brain injury and exert neuroprotective effects in hypoxic-ischemic (HI). In brain homogenate, 5k significantly improves the activity of MDA, SOD, GSH-Px, CAT and T-AOC to exert its beneficial effect against oxidative stress induced by HI injury. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.04.031
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 3'-氟苯乙酮 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 以88%的产率得到(E)-3-(dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Enaminones作为定向C H功能化的合成子：RhIII催化的萘合成

  摘要：

  据报道，使用烯胺酮作为有效的合成子进行有针对性的CH功能化。基于烯胺酮与炔烃或α-重氮-β-酮酸酯的偶联，已经开发了用于Rh III催化的萘合成的概念验证方案。两个固有的反应性官能团（羟基和醛基）被整合到新形成的环状骨架中，并且可以耐受广泛的取代基，从而使目标产物易于进一步加工。

  DOI：

  10.1002/anie.201603943

文献信息

• 6-N-Linked Heterocycle-Substituted 2,3,4,5-Tetrahydro-1H-Benzo[d]Azepines as 5-Ht2c Receptor Agonists
  申请人：Briner Karin

  公开号：US20080214520A1

  公开（公告）日：2008-09-04

  The present invention provides 6-substituted 2,3,4,5-tetrahydro-1H-benzo[d]azepines of Formula I as selective 5-HT 2C receptor agonists for the treatment of 5-HT 2C associated disorders including obesity, obsessive/compulsive disorder, depression, and anxiety: Formula (I) where: R 6 is selected from the group consisting of (a, b, c, d, e) and other substituents are as defined in the specification.

  本发明提供了Formula I的6-取代的2,3,4,5-四氢-1H-苯并[d]氮杂环庚烯作为选择性5-HT2C受体激动剂，用于治疗与5-HT2C相关的疾病，包括肥胖症、强迫症、抑郁症和焦虑症：Formula (I)其中：R6选自(a、b、c、d、e)等基团组成的群，其他取代基如规范中定义。
• Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C–C Coupling Reactions
  作者：Chao Song、Chen Yang、Hua Zeng、Wenjing Zhang、Shan Guo、Jin Zhu

  DOI：10.1021/acs.orglett.8b01406

  日期：2018.7.6

  Rh(III)-catalyzed enaminone-directed C–H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C–C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C–C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved.

  Rh（III）催化的与α-重氮-α-膦酰基乙酸酯结合的烯胺酮定向的C–H偶联已用于鉴定氟化物介导的膦酰基化的C–C偶联反应，用于合成4-羟基-1-萘甲酸酯。还实现了α-膦酰基乙酸酯和苯甲醛的分子间CC偶联，用于（E）-选择性α，β-不饱和酯的合成。
• Method of using substituted pyrazolo [1,5-a] pyrimidines
  申请人：Wang Daniel Yanong

  公开号：US20060063784A1

  公开（公告）日：2006-03-23

  This invention relates to novel methods of use of certain pyrazolo[1,5-a]pyrimidine compounds and the therapeutically acceptable salts thereof. This invention also relates to novel methods of using these compounds as anti-proliferative agents in mammals, including humans.

  这项发明涉及某些吡唑并[1,5-a]嘧啶化合物及其治疗上可接受的盐的新用途方法。该发明还涉及将这些化合物作为抗增殖剂在哺乳动物，包括人类中的新用途方法。
• [EN] PYRIDOPYRIMIDINES AND METHODS OF THEIR USE<br/>[FR] PYRIDOPYRIMIDINES ET LEURS MÉTHODES D'UTILISATION
  申请人：YUMANITY THERAPEUTICS INC

  公开号：WO2021247859A1

  公开（公告）日：2021-12-09

  Disclosed are compounds useful in the treatment of neurological disorders. The compounds described herein, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological diseases.

  本文披露了在治疗神经系统疾病中有用的化合物。这些化合物可以单独或与其他药理活性剂结合使用，用于治疗或预防神经系统疾病。
• Electrochemical oxidative thiocyanation and amination of enaminones towards the synthesis of multi-substituted alkenes
  作者：Fangling Lu、Kan Zhang、Yanxiu Yao、Ying Yin、Jiafu Chen、Xinwei Zhang、Yin Wang、Lijun Lu、Ziwei Gao、Aiwen Lei

  DOI：10.1039/d0gc03590d

  日期：——

  A highly stereoselective synthesis of thiocyanated enaminones was achieved by an electrochemical process, which involved C–H bond thiocyanation and vinyl C–N bond transamination. Various aryl enaminones were compatible, generating the desired thiocyanated enaminones in up to 87% yields. This transformation proceeded smoothly without an external oxidant, a supporting electrolyte and a transition-metal

  硫氰酸化的烯胺酮的高度立体选择性合成是通过电化学过程实现的，该过程涉及C–H键硫氰化和乙烯基C–N键氨基转移。各种芳基烯胺酮均相容，以高达87％的收率产生所需的硫氰酸化烯胺酮。在没有外部氧化剂，支持电解质和过渡金属催化剂的情况下，该转化顺利进行。克级合成显示了该协议在实际应用中的潜力。