(E)-3-(4-fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one

• 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: (E)-3-(4-fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₀FNO₃
• 分子量: 271.248
• InChiKey: DJMPHYOHRPBGFO-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one 在 氢气 、 magnesium oxide 作用下， 以 邻二甲苯 为溶剂， 70.0 ℃ 、900.01 kPa 条件下， 反应 0.75h， 以65%的产率得到(E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones

  摘要：

  2'-Aminochalcones of pharmaceutical and commercial interest have been obtained in high yields and selectivities through a one-pot process using a bifunctional heterogeneous catalyst bearing base and metal active sites. This is a physical mixture material formed by a high-surface-area MgO and Pt on TiO2. The process involves as the first step the Claisen-Schmidt condensation between o-nitroacetophenone and benzaldehyde derivatives on the basic catalytic function. This is followed by a chemoselective hydrogenation of the nitro group in the presence of the carbonyl and double-bond carbon carbon groups within the molecule. Using the bifunctional catalyst and the reaction system proposed here, it is possible to produce, under mild reaction conditions and short reaction times, 2'-aminochalcones with higher yields and selectivities than those obtained by conventional multistep methods.

  DOI：

  10.1021/cs5011713
• 作为产物：
  描述：

  邻硝基苯乙酮 、 对氟苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以91%的产率得到(E)-3-(4-fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  邻硝基查尔酮意外环化为 2-亚烷基吲哚啉-3-酮

  摘要：

  描述了一种从邻硝基查耳酮制备 2-(3-oxindolin-2-ylidene) 乙腈的原始、简便且高效的方法。特征转化是氰化物阴离子触发的迈克尔加成到查尔酮，然后是与 Baeyer-Drewson 反应机制相关的级联环化。

  DOI：

  10.1039/d0ra03520c

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING OR PREVENTING HEART FAILURE<br/>[FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT OU DE PRÉVENTION D'INSUFFISANCE CARDIAQUE
  申请人：UNIV DREXEL

  公开号：WO2020146636A1

  公开（公告）日：2020-07-16

  The present invention relates to the discovery of novel compounds that can be used to treat and/or prevent heart failure in a subject. In certain embodiments, the compounds of the invention are sulfide: quinone oxidoreductase (SQOR) inhibitors. In other embodiments, the compounds of the invention increase physiological levels of H2S in the subject. In yet other embodiments, administration of the compounds of the invention treats and/or prevents hypertension, and/or atherosclerosis, and/or pathological cardiac remodeling that leads to heart failure in the subject.

  本发明涉及发现的新化合物，可用于治疗和/或预防受试者的心力衰竭。在某些实施例中，本发明的化合物是硫化物：喹喔醌氧还酶（SQOR）抑制剂。在其他实施例中，本发明的化合物增加受试者体内H2S的生理水平。在另一些实施例中，给予本发明的化合物治疗和/或预防受试者的高血压，和/或动脉粥样硬化，和/或导致心力衰竭的病理性心脏重塑。
• Synthesis of 2-(1<i>H</i>-Indol-2-yl)acetamides via Brønsted Acid-Assisted Cyclization Cascade
  作者：Nicolai A. Aksenov、Dmitrii A. Aksenov、Anton A. Skomorokhov、Lidiya A. Prityko、Alexander V. Aksenov、Georgii D. Griaznov、Michael Rubin

  DOI：10.1021/acs.joc.0c01344

  日期：2020.10.2

  efficient and straightforward Brønsted-acid mediated cascade process was developed, involving cyclization of readily available β-ketonitriles into 2-aminofurans, and their subsequent recyclization into 2-(1H-indol-2-yl)acetamides is developed. This synthetic route opens a new avenue for an expeditious assembly of various isotryptamine derivatives for medicinal chemistry.

  开发了一种有效且直接的布朗斯台德酸介导的级联过程，涉及将容易获得的β-酮腈环化为2-氨基呋喃，并随后将其环化为2-（1 H-吲哚-2-基）乙酰胺。该合成路线为快速组装用于药物化学的各种异色胺衍生物开辟了一条新途径。
• Synthesis, biological activities, and docking study of novel chalcone‐pleuromutilin derivatives
  作者：Chuan Xie、Siyu Zhang、Wei Zhang、Chunxia Wu、Can Yong、Yuhao Sun、Zhengxing Zeng、Qian Zhang、Zixin Huang、Tian Chen、Yuanyuan Zhang

  DOI：10.1111/cbdd.13692

  日期：2020.8

  discover novel antibiotics. The diterpene natural pleuromutilin is a prominent candidate for its special mode of action by inhibiting protein synthesis. In this study, a series of novel pleuromutilin derivatives with chalcone moiety was designed and synthesized, and their antibacterial activities were assessed in vitro. As suggested from the results, most of compounds exhibited potent activities against

  这些天，抗生素抗性问题变得越来越严重，解决该问题的可行解决方案是开发和发现新型抗生素。二萜天然截短侧耳素因其通过抑制蛋白质合成的特殊作用方式而成为重要候选者。在这项研究中，设计和合成了一系列具有查耳酮部分的截短侧耳素新衍生物，并在体外评估了它们的抗菌活性。结果表明，大多数化合物对两种耐甲氧西林的金黄色葡萄球菌均具有有效的活性。（MRSA）ATCC 33591和43300。随后对查尔酮结构，氮杂环衍生物进行了进一步修饰，然后进行了评估，并报道了其对测试菌株的有效活性。进行了初步的对接研究，以探索目标分子与结合位点之间的相互作用。
• Transition Metal-Free Iodine-Catalyzed Denitrative C–S Cross-Coupling: An Atypical Route to Access Thiochromane Derivatives
  作者：Anuradha Nandy、Govindasamy Sekar

  DOI：10.1021/acs.joc.2c00425

  日期：2022.6.3

  extended for a three-component synthesis of thiochromenes via intermolecular C–S cross-coupling followed by aldol reaction. The reaction proceeds via activation of the keto group of chalcone through a halogen bond complex with iodine/denitrative C–S bond formation with xanthate/sulfa-Michael addition to chalcones. The methodology was also demonstrated for chemoselective reduction of chalcones. The protocol

  已经开发了一种碘催化的脱硝 C-S 交叉偶联反应，以从 2'-硝基查耳酮和黄原酸盐中获得硫色酮。该策略被扩展为通过分子间 C-S 交叉偶联和醛醇反应合成三组分硫色素。该反应通过与碘/脱硝的 C-S 键形成的卤素键络合物活化查尔酮的酮基而进行，黄原酸盐/磺胺-迈克尔加成到查尔酮上。该方法也被证明可用于化学选择性还原查尔酮。该协议还用于合成生物学上重要的 3'-羟基硫黄酮和硫色素酮。
• A Diastereoselective Assembly of Tetralone Derivatives via a Tandem Michael Reaction and <i>ipso</i>-Substitution of the Nitro Group
  作者：Nicolai A. Aksenov、Dmitrii A. Aksenov、Daniil D. Ganusenko、Igor A. Kurenkov、Alexander V. Aksenov

  DOI：10.1021/acs.joc.3c00134

  日期：2023.5.5

  A highly diastereoselective tandem reaction of 2′-nitrochalcones is reported, involving Michael addition and a subsequent ipso-substitution of the nitro group to produce 1-tetralones with two contiguous chiral centers. A related annulation reaction of 2′-nitrochalcones with potassium cyanide affording 1-indanones with a C3-quaternary chiral center is also demonstrated.

  报道了 2'-硝基查尔酮的高度非对映选择性串联反应，涉及迈克尔加成和随后硝基的ipso取代，以产生具有两个连续手性中心的 1-四氢萘酮。还证明了 2'-硝基查耳酮与氰化钾的相关环化反应，得到具有 C3-季手性中心的 1-茚满酮。