1-(4-(dimethylamino)phenyl)prop-2-en-1-one | 34834-15-6

• 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: 1-(4-(dimethylamino)phenyl)prop-2-en-1-one
• 英文别名: 1-[4-(Dimethylamino)phenyl]prop-2-en-1-one
• CAS: 34834-15-6
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: XWGPLFGFPVPPCM-UHFFFAOYSA-N

物化性质

• 沸点：
  294.4±32.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 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：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-(dimethylamino)phenyl)prop-2-en-1-one 在 ammonium acetate 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Structure–activity studies of 5-substituted pyridopyrimidines as adenosine kinase inhibitors

  摘要：

  The synthesis and SAR of a novel series of non-nucleoside pyridopyrimidine inhibitors of the enzyme adenosine kinase (AK) are described. It was found that pyridopyrimidines with a broad range of medium and large non-polar substituents at the 5-position potently inhibited AK activity. A narrower range of analogues was capable of potently inhibiting adenosine phosphorylation in intact cells indicating an enhanced ability of these analogues to penetrate cell membranes. Potent AK inhibitors were found to effectively reduce nociception in animal models of thermal hyperalgesia and persistent pain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00602-8
• 作为产物：
  描述：

  (4-chlorophenacyl)triphenylphosphonium bromide 在 sodium hydroxide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 生成 1-(4-(dimethylamino)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Structure–activity studies of 5-substituted pyridopyrimidines as adenosine kinase inhibitors

  摘要：

  The synthesis and SAR of a novel series of non-nucleoside pyridopyrimidine inhibitors of the enzyme adenosine kinase (AK) are described. It was found that pyridopyrimidines with a broad range of medium and large non-polar substituents at the 5-position potently inhibited AK activity. A narrower range of analogues was capable of potently inhibiting adenosine phosphorylation in intact cells indicating an enhanced ability of these analogues to penetrate cell membranes. Potent AK inhibitors were found to effectively reduce nociception in animal models of thermal hyperalgesia and persistent pain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00602-8

文献信息

• Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3‐Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses
  作者：Marvin Stephan、Jesco Panther、Fabio Wilbert、Pauline Ozog、Thomas J. J. Müller

  DOI：10.1002/ejoc.202000066

  日期：2020.4.16

  The Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using CataCXium® Ptb as a ligand, NaHCO3 as a base, and nBu4NCl provides an efficient access to 3‐(hetero)aryl propenals/propenones, which are directly employed in consecutive multicomponent syntheses of pyrazoles in a one‐pot fashion.

  使用CataCXium®Ptb作为配体，NaHCO 3作为碱和n Bu 4 NCl进行（杂）芳基溴化物和丙烯醛或乙烯基酮的Heck反应，可以有效地获得3-（杂）芳基丙烯/丙烯酮。以单罐方式直接用于吡唑的连续多组分合成中。
• Design of 2‐Pyridone Fluorophores for Brighter Emissions at Longer Wavelengths
  作者：Dong Sun Kim、Younghun Kim、Dongwhan Lee、Yan Lee

  DOI：10.1002/chem.202303458

  日期：2024.3.12

  sentence: A rational design strategy for 2-pyridone-based fluorophores with bright emission at long wavelengths is proposed. An intramolecular charge transfer-based 2-pyridone fluorophore with large molar absorptivity (ϵ=20,100 M−1 cm−1), longer emission wavelength (λem=539 nm), high emission quantum yield (ϕF=74 %), and large Stokes shift (Δv=5720 cm−1) is developed by the strategy.

  TOC 句子：提出了一种在长波长下具有明亮发射的基于 2-吡啶酮的荧光团的合理设计策略。基于分子内电荷转移的2-吡啶酮荧光团，具有大摩尔吸收率（ϵ=20,100 M −1 cm −1 ）、更长的发射波长（λ em =539 nm）、高发射量子产率（Φ F =74 %），以及该策略产生了大的斯托克斯位移（Δv=5720 cm -1 ）。
• Pyridinverbindungen und deren Verwendung
  申请人：BASF Aktiengesellschaft

  公开号：EP0261602A2

  公开（公告）日：1988-03-30

  Es werden Pyridinverbindungen der allgemeinen Formel beschrieben, in der ein X für Phenyl und das andere X für durch Halogen, Cyano, C₁- bis C₅-Alkyl, C₁- bis C₅-Alkoxy oder C₁-C₅-Alkoxycarbonyl substituiertes Phenyl oder beide X für 4-Fluorphenyl und X¹ für einen der Reste der Formeln stehen, worin R¹    und R² unabhängig voneinander lineares oder verzweigtes Akyl, Cyanalkyl, Halogenalkyl, Aryl oder Aralkyl mit insgesamt 7 bis 14 C-Atomen oder einen 5- oder 6-gliedrigen gesättigten heterocyclischen Rest und R³    lineares oder verzweigtes C₁- bis C₄-Alkyl bedeuten. Die Verbindungen (I) sind Farbbildner für druckempfindliche Aufzeichnungssysteme.

  通式如下的吡啶化合物 其中一个 X 是苯基，另一个 X 是被卤素、氰基、C₁- 至 C₅-烷基、C₁- 至 C₅-烷氧基或 C₁-C₅-烷氧基羰基取代的苯基，或两个 X 都是 4-氟苯基，且 X¹ 是式中的一个基团的吡啶化合物 是 其中 R¹ 和 R² 相互独立地是具有 7 至 14 个碳原子的直链或支链烷基、氰基烷基、卤代烷基、芳基或芳烷基，或 5 或 6 元饱和杂环基，且 R³ 是线性或支链 C₁- 至 C₄- 烷基。 化合物 (I) 是压敏记录系统的显色剂。
• New pyridin-3-ylmethyl carbamodithioic esters activate pyruvate kinase M2 and potential anticancer lead compounds
  作者：Yu Zhang、Bin Liu、Xingyu Wu、Ridong Li、Xianling Ning、Yu Liu、Zhenming Liu、Zemei Ge、Runtao Li、Yuxin Yin

  DOI：10.1016/j.bmc.2015.05.041

  日期：2015.8

  Pyruvate kinase M2 (PKM2) is a key protein responsible for cancer's Warburg effect. Activation of PKM2 may alter aberrant metabolism in cancer cells, which suggests PKM2 as a tumor selective therapeutic target. In this paper, the lead compound 8 was first discovered as a new kind of PKM2 activator from a random screening of an in-house compound library. Then, a series of lead compound 8 analogs were designed, synthesized and evaluated for their activation of PKM2 and anticancer activities. 7-Azaindole analog 32 was identified as the most potent PKM2 activator. Compounds with potent enzyme activity also exhibited selective anti-proliferation activity on cancer cell lines HCT116, Hela and H1299 compared with non-tumor cell line BEAS-2B. The structure-activity relationships of these compounds were supported by molecular docking results. Preliminary pharmacological studies also showed that compound 32 arrests the cell cycle at the G2/M phase in HCT116 cell line. (C) 2015 Elsevier Ltd. All rights reserved.
• Tetraazaannulene cobalt complex compounds and method for preparation thereof
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0073456B1

  公开（公告）日：1985-11-27