4-(3',4'-dichlorobenzylidene)-2-phenyl-4-oxazolone | 1037-02-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(3',4'-dichlorobenzylidene)-2-phenyl-4-oxazolone
• 英文别名: 2-Phenyl-4-<3,4-dichlor-benzyliden>-4H-<1,3> oxazol-5-on；4-(3,4-dichloro-benzylidene)-2-phenyl-4H-oxazol-5-one；4-[(3,4-Dichlorophenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 1037-02-1
• 化学式: C₁₆H₉Cl₂NO₂
• mdl: MFCD00125907
• 分子量: 318.159
• InChiKey: MYUAUDNSRVTJCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3',4'-dichlorobenzylidene)-2-phenyl-4-oxazolone 在 尿素 作用下， 以 乙二醇 为溶剂， 反应 0.1h， 以85%的产率得到4-(3,4-dichlorobenzylidene)-2-phenyl-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  级联反应的扩展：GFP生色团衍生物的微波辅助合成

  摘要：

  咪唑-5（4 H）-1衍生物的微波辅助简便合成是通过4-芳基亚甲基-2-苯基恶唑-5（4 H）-1与脲（或醋酸铵）在乙二醇中的反应完成的。级联反应易于进行，并且在温和条件下发生，适用范围广。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.315
• 作为产物：
  描述：

  马尿酸 、 3,4-二氯苯甲醛 在 乙酸酐 作用下， 生成 4-(3',4'-dichlorobenzylidene)-2-phenyl-4-oxazolone
  参考文献：
  名称：

  通过新型级联反应有效合成新型吡唑并[3,4- b ]吡啶-6-一衍生物

  摘要：

  描述了一种新的4-亚芳基-2-苯基-1,3-恶唑-5（4 H）-与3-甲基-1-苯基-1 H-吡唑-5-胺的级联反应，许多新的合成了吡唑并[3,4- b ]吡啶-6-衍生物。该新协议的优点是时间更短，产量更高，成本更低以及操作更简便。

  DOI：

  10.1002/jhet.5570440506

文献信息

• Construction of adjacent spiro-quaternary and tertiary stereocenters through phosphine-catalyzed asymmetric [3+2] annulation of allenoates with alkylidene azlactones
  作者：De Wang、Yin Wei、Min Shi

  DOI：10.1039/c2cc17709a

  日期：——

  A novel axially chiral spiro-phosphine-catalyzed highly regio-, diastereo- and enantioselective [3+2] cycloaddition of alkylidene azlactones with various allenic esters has been developed, affording the corresponding functionalized spirocyclic products in moderate to excellent yields under mild conditions. These spirocyclic products as masked amino acids can be easily transformed into aspartic amino

  已开发出一种新型的轴向手性螺膦催化的亚烷基氮杂内酯与各种烯丙基酯的高度区域，非对映和对映选择性[3 + 2]环加成反应，可在温和条件下以中等至优异的收率提供相应的官能化螺环产物。这些螺环产物作为被掩盖的氨基酸可以容易地转化为天冬氨酸类似物。
• Orthopalladation of GFP-Like Fluorophores Through C-H Bond Activation: Scope and Photophysical Properties
  作者：Sandra Collado、Alejandro Pueyo、Christine Baudequin、Laurent Bischoff、Ana Isabel Jiménez、Carlos Cativiela、Christophe Hoarau、Esteban P. Urriolabeitia

  DOI：10.1002/ejoc.201800966

  日期：2018.12.2

  C. H. and E. P. U. thank the European Cooperation in Science and Technology (COST) program under CA15106 grant: CH Activation in Organic Synthesis (CHAOS). A. I. J., C. C. and E. P. U. thank Ministerio de Economia y Competitividad MINECO (Spain, Project CTQ2013‐40855R) and Gobierno de Aragon‐FEDER (Spain, research group E19_17R: Aminoacidos y Peptidos) for financial support. This work has been partially

  CH 和 EPU 感谢 CA15106 资助下的欧洲科学技术合作 (COST) 计划：有机合成中的 CH 激活 (CHAOS)。AIJ、CC 和 EPU 感谢Ministryio de Economia y Competitividad MINECO（西班牙，CTQ2013-40855R 项目）和 Gobierno de Aragon-FEDER（西班牙，研究组 E19_17R：Aminoacidos y Peptidos）提供的资金支持。这项工作得到了鲁昂大学、鲁昂国家应用科学研究院 (INSA Rouen)、国家科学研究中心 (CNRS)、卓越实验室 (Labex) SynOrg 和诺曼底地区的部分支持。
• An efficient route for the synthesis of a new class of pyrido[2,3-d]pyrimidine derivatives
  作者：Shujiang Tu、Junyong Zhang、Runhong Jia、Bo Jiang、Yan Zhang、Hong Jiang

  DOI：10.1039/b617201f

  日期：——

  A new reaction of 4-arylidene-3-methylisoxazol-5(4H)-one or 4-arylidene-2-phenyloxazol-5(4H)-one with 2,6-diaminopyrimidin-4(3H)-one is described and a number of new pyrido[2,3-d]pyrimidine-4,7-dione derivatives are synthesized. This protocol has the advantages of good yields, broad substrate scope and simple work-up.

  描述了一种新的4-亚芳基-3-甲基异恶唑-5（4H）-1或4-亚芳基-2-苯基恶唑-5（4H）-1与2,6-二氨基嘧啶-4（3H）-1的新反应。合成了许多新的吡啶并[2,3-d]嘧啶-4,7-二酮衍生物。该方案具有良率高，底物范围广，后处理简单的优点。
• Diastereo- and Enantioselective Construction of the Hexahydrocoumarin Scaffold via an Organocatalytic Asymmetric [3 + 3] Cyclization
  作者：Xue Yang、Yu-Chen Zhang、Qiu-Ning Zhu、Man-Su Tu、Feng Shi

  DOI：10.1021/acs.joc.6b00603

  日期：2016.6.17

  The first catalytic asymmetric construction of the biologically important hexahydrocoumarin scaffold has been established, which takes advantage of chiral thiourea–tertiary amine-catalyzed enantioselective transformations. Besides, this reaction also realized the first catalytic asymmetric [3 + 3] cyclization of 4-arylidene-2-aryloxazol-5(4H)-ones with cyclohexane-1,3-diones, which afforded structurally

  已经建立了生物学上重要的六氢香豆素骨架的第一个催化不对称结构，该结构利用了手性硫脲-叔胺催化的对映选择性转化。此外，该反应还实现了4-亚芳基-2-芳基恶唑-5（4 H）-环己烷-1,3-二酮类化合物，可提供结构多样的3-氨基六氢香豆素衍生物，具有出色的非对映选择性和高对映选择性（均> 95：5 dr，最高达96：4 er）。对活化方式的研究表明，手性硫脲-叔胺催化剂通过氢键相互作用同时活化了两种底物。而且，该反应可用于大规模的对映体富集的六氢香豆素的合成。这种方法不仅为构建手性六氢香豆素骨架提供了一种有效的方法，而且丰富了不对称有机催化和催化对映选择性[3 + 3]环化的研究领域。
• Synthesis and evaluation of a series of novel imidazolidinone analogues of 6-aminoflavone as anticancer and anti-inflammatory agents
  作者：Sudheer Moorkoth、K. K. Srinivasan、N. Gopalan Kutty、Alex Joseph、M. Naseer

  DOI：10.1007/s00044-013-0486-7

  日期：2013.10

  The flavone moiety is a potential pharmacophore known for its diverse range of pharmacological activities. Aminoflavones have recently been the subject of considerable attention as lead molecules in several cancer research projects. Imidazolidinone heterocycles represent another biologically active scaffold with known cytotoxic properties. In an attempt to provide synergistic cytotoxic activity, these two moieties have been combined, and the resulting novel analogues evaluated for their anticancer and anti-inflammatory activities. The results revealed that the cytotoxicities of these compounds were fivefold greater than those of aminoflavone. DNA histograms obtained from cell cycle analysis in the presence of these compounds were apoptotic in their nature. Furthermore, the in vivo screening of these compounds using Ehrlich's ascites tumour model showed an increase in life span, whereas an in vivo anti-inflammatory study resulted in the enhancement of the anti-inflammatory potential. The results therefore supported the hypothesis that there is a relationship between inflammation and cancer.