(E)-3-(dimethylamino)-1-(2-fluorophenyl)prop-2-en-1-one | 138716-19-5

• 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-(2-fluorophenyl)prop-2-en-1-one
• CAS: 138716-19-5
• 化学式: C₁₁H₁₂FNO
• 分子量: 193.221
• InChiKey: CJIYFDMXXQURKM-BQYQJAHWSA-N

物化性质

• 沸点：
  270.3±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-(2-fluorophenyl)prop-2-en-1-one 在 ammonium acetate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 (Z)-6-(2-fluorophenyl)-2-methyl-N'-(1-methyl-2-oxoindolin-3-ylidene)nicotinohydrazide
  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：

  2'-氟苯乙酮 在 N,N-二甲基甲酰胺二甲基缩醛 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(dimethylamino)-1-(2-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and

  摘要：

  这份披露描述了具有抗焦虑活性的取代的1,2,4-三氮唑[1,5-a]嘧啶和取代的1,2,4-三氮唑[4,3-a]嘧啶。

  公开号：

  US04209621A1

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。
• Fluoride catalyzed P–aryl-coupling—a mild approach to functionalized arylphosphines
  作者：Andreas Reis、Daniel Dehe、Saeid Farsadpour、Isabel Munstein、Yu Sun、Werner R. Thiel

  DOI：10.1039/c1nj20448c

  日期：——

  Functionalized triaryl- and diarylalkylphosphines are accessible in high yields following a mild fluoride catalyzed phosphorous–carbon coupling protocol starting from fluoroarenes and silylated phosphines. The reaction requires a minimum of solvent and can be applied to the synthesis of several functionalized phosphines on a kilogram scale without problems. In contrast to the phosphine synthesis in a superbasic medium, there is no salt formation during the reaction which simplifies the work-up process.

  经过温和的氟化物催化磷-碳偶联反应，可以从氟代芳烃和硅烷化的膦高效地获得高产率的官能化三芳基膦和二芳基烷基膦。该反应所需的溶剂最少，并且可以在不遇到问题的情况下应用于公斤级规模的多种官能化膦的合成。与在超碱介质中进行的膦合成不同，反应过程中没有盐的形成，从而简化了后续处理流程。
• A new approach for the synthesis of novel naphthoquinone chalcone hybrid compounds
  作者：Ha-Thanh Nguyen、Tuyet Anh Dang Thi、Phuong Hoang Thi、Giang Le-Nhat-Thuy、Quynh Giang Nguyen Thi、Anh Nguyen Tuan、Tu Anh Le Thi、Tuyen Van Nguyen

  DOI：10.1016/j.tetlet.2021.153337

  日期：2021.9

  A facile and efficient synthesis of novel naphthoquinone-based chalcone hybrids ( and ) the microwave-assisted one-pot three-component reactions of 2-substituted-1,4-naphthoquinones, ,-dimethylformamide dimethyl acetal (DMF-DMA), and acetophenone derivatives has been reported. Whereas the synthesis of hybrids proceeded a condensation, 1,4-addition, rotation, elimination, and [1,3]-H shift sequence

  新型萘醌基查尔酮杂化物的简便高效合成（和）2-取代-1,4-萘醌、,-二甲基甲酰胺二甲基缩醛（DMF-DMA）和苯乙酮的微波辅助一锅三组分反应衍生品已有报道。杂化物的合成是通过缩合、1,4-加成、旋转、消除和[1,3]-H移位顺序进行的，而杂化物的合成是通过包括缩合、1,4-加成、旋转、消除和[1,3]-H转移的三步顺序形成的。 -加成反应和消除反应。
• Synthesis of Substituted 1‐Hydroxy‐2‐Naphthaldehydes by Rhodium‐Catalyzed C−H Bond Activation and Vinylene Transfer of Enaminones with Vinylene Carbonate
  作者：Min Liu、Kelu Yan、Jiangwei Wen、Weihua Liu、Mingyu Wang、Lina Wang、Xiu Wang

  DOI：10.1002/adsc.202101181

  日期：2022.2

  The rhodium(III)-catalyzed C−H bond activation and vinylene transfer of enaminones with vinylene carbonate have been proposed for the synthesis of substituted 1-hydroxy-2-naphthaldehydes in 49–84% yields. Several preliminary mechanistic studies and hydroxyl-directed derivatization reactions of 1-hydroxy-2-naphthaldehydes were also performed. This method offers an alternative approach for the synthesis

  已经提出了铑（III）催化的 C-H 键活化和烯胺酮与碳酸亚乙烯酯的亚乙烯基转移，以 49-84% 的产率合成取代的 1-羟基-2-萘醛。还进行了几项初步机理研究和 1-羟基-2-萘醛的羟基定向衍生反应。该方法为合成 1-羟基-2-萘醛提供了一种替代方法。