(E)-1-(2-methoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one | 1309371-20-7

• 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)-1-(2-methoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one
• CAS: 1309371-20-7
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: ONFFVLQFJTYEPI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-methoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one 在 4,4'-联吡啶 、 四羟基二硼 作用下， 以 二甲基亚砜 为溶剂， 25.0~170.0 ℃ 、1.0 MPa 条件下， 反应 0.11h， 生成 2-(2-甲氧基苯基)喹啉
  参考文献：
  名称：

  通过固定手性磷酸催化和二硼酸介导的选择性硝基还原实现四氢喹啉 SERM 的对映选择性流动合成

  摘要：

  据报道，一种不对称对映选择性流程用于正式合成 1,2,3,4-四氢喹啉选择性雌激素受体调节剂。从容易获得的 2-硝基查耳酮开始，该过程的第一部分包括使用二硼酸作为简单还原剂的伸缩硝基还原/分子内环缩合序列。随后在固定化磷酸有机催化剂存在下进行对映选择性转移氢化，然后进行伸缩式 N-烷基化，得到目标手性中间体。该方法确保了合成规模的灵活性，同时最大限度地减少中间纯化的需要并确保环境友好的无金属条件。

  DOI：

  10.1002/adsc.202301387
• 作为产物：
  描述：

  邻甲氧基-2-溴苯乙酮 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (E)-1-(2-methoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  从2-氨基查耳酮的可见光驱动合成多环苯并[d] [1,3]恶唑啉。

  摘要：

  在本文中，我们报告了2-氨基查尔酮与可见光驱动的双功能亲核试剂的串联环异构化/亲核加成/环化反应。这种级联过程是通过在室温下照射蓝色LED来实现的，这为结构上多样化的苯并[ d ] [1,3]恶唑啉骨架提供了一条简洁的途径。机理研究表明，反应是在可见光照射下，由C–C双键的E到Z异构化开始的，然后环化/再芳构化以生成瞬态喹啉中间体，该中间体被亲核试剂捕获并环化生成多环苯并[ d ] [1,3]恶唑啉。

  DOI：

  10.1039/d0cc02416c

文献信息

• Blue-light-promoted carbon–carbon double bond isomerization and its application in the syntheses of quinolines
  作者：Xinzheng Chen、Shuxian Qiu、Sasa Wang、Huifei Wang、Hongbin Zhai

  DOI：10.1039/c7ob00558j

  日期：——

  A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.

  据报道在没有任何光氧化还原催化剂的情况下，蓝光促进的碳-碳双键异构化。在简单的有氧条件下，它可以快速获得一系列喹啉，收率好至极好。该方案是直接，无催化剂且操作方便的。
• [EN] NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER<br/>[FR] MODULATEURS DE RÉCEPTEURS NUCLÉAIRES ET LEUR UTILISATION POUR LE TRAITEMENT ET LA PRÉVENTION D'UN CANCER
  申请人：US HEALTH

  公开号：WO2012174436A1

  公开（公告）日：2012-12-20

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.

  本文披露了一些化合物，它们是核受体调节剂，可以作为雄激素受体的拮抗剂，例如，公式I的化合物：其中R1至R5和X1至X5如本文所述，以及其药用盐、溶剂化合物和立体异构体。还披露了包括这些化合物的药物组合物，以及使用方法和治疗癌症，包括前列腺癌、其他核受体介导的癌症和其他疾病的方法。
• Organocatalytic Enantioselective Cascade Aza‐Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines
  作者：Wen Yang、Hai‐Xiao He、Yu Gao、Da‐Ming Du

  DOI：10.1002/adsc.201300670

  日期：2013.12.16

  AbstractAn efficient organocatalytic highly asymmetric cascade aza‐Michael/Michael addition reaction for the synthesis of tetrahydroquinolines and tetrahydrochromanoquinolines has been developed. This cascade reaction proceeds well at low catalyst loading with a broad substrate scope, furnishing the desired products in excellent yields with excellent diastereoselectivities and enantioselectivities (up to >99:1 dr, 99% ee) under mild conditions. Importantly, it is the first catalytic asymmetric method for tetrahydrochromanoquinolines. This protocol provides a straightforward entry to highly functionalized chiral tetrahydroquinoline and tetrahydrochromanoquinoline derivatives from simple starting materials.magnified image
• Novel Chalcone Derivatives as Potent Nrf2 Activators in Mice and Human Lung Epithelial Cells
  作者：Vineet Kumar、Sarvesh Kumar、Mohammad Hassan、Hailong Wu、Rajesh K. Thimmulappa、Amit Kumar、Sunil K. Sharma、Virinder S. Parmar、Shyam Biswal、Sanjay V. Malhotra

  DOI：10.1021/jm2002348

  日期：2011.6.23

  Nrf2-mediated activation of antioxidant response element is a central part of molecular mechanisms governing the protective function of phase II detoxification and antioxidant enzymes against carcinogenesis, oxidative stress, and inflammation. Nrf2 is sequestered in the cytoplasm by its repressor, Keap1. We have designed and synthesized novel chalcone derivatives as Nrf2 activators. The potency of these compounds was measured by the expression of Nrf2 dependent antioxidant genes GCLM, NQO1, and HO1 in human lung epithelial cells, while the cytotoxicity was analyzed using MTT assay. In vivo potency of identified lead compounds to activate Nrf2 was evaluated using a mouse model. Our studies showed 2-trifluoromethyl-2'-methoxychalone (2b) to be a potent activator of Nrf2, both in vitro and in mice. Additional experiments showed that the activation of Nrf2 by this compound is independent of reactive oxygen species or redox changes. We have discussed a quantitative structure-activity relationship and proposed a possible mechanism of Nrf2, activation.
• A strategy to access fused triazoloquinoline and related nucleoside analogues
  作者：Kapil Upadhyaya、Arya Ajay、Rohit Mahar、Renu Pandey、Brijesh Kumar、Sanjeev K. Shukla、Rama Pati Tripathi

  DOI：10.1016/j.tet.2013.07.088

  日期：2013.10

  Fused triazoloquinolines have been prepared starting from (E)-3-(2-nitrophenyl)-1-aryl-prop-2-en-1-ones and sugar or benzyl azides in a sequential [3+2] cycloaddition reaction, followed by one pot Pd-C assisted reduction, cyclization and aromatization. The triazolyl fused quinolines with N-1-glycosyl substituents as unnatural nucleosides have inherent potential to generate a library of compounds for bioevaluations. (C) 2013 Elsevier Ltd. All rights reserved.