4-氰基-2'-羟基查尔酮 | 79610-67-6

• 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
• 中文名称: 4-氰基-2'-羟基查尔酮
• 英文名称: 4-cyano-2'-hydroxychalcone
• 英文别名: (E)-4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzonitrile；4-[3-(2-Hydroxyphenyl)-3-oxoprop-1-enyl]benzonitrile；4-[(E)-3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]benzonitrile
• CAS: 79610-67-6
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: NLXKPBYOVGGPRF-MDZDMXLPSA-N

物化性质

• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氰基-2'-羟基查尔酮 以54%的产率得到
  参考文献：
  名称：

  PATONAY, T.;LITKEI, G.;ZSUGA, M.;KISS, A., ORG. PREP. AND PROCED. INT., 1984, 16, N 5-6, 315-319

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基二乙基氨基甲酸酯 在 lithium diisopropyl amide 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-氰基-2'-羟基查尔酮
  参考文献：
  名称：

  从氨基甲酸酯到查尔酮：连续的阴离子炸薯条重排，阴离子Si→C烷基重排和Claisen–Schmidt缩合

  摘要：

  开发了一种高效的一锅法，可从苯基二乙基氨基甲酸酯合成各种2'-羟基查耳酮，其特征是连续进行一次Snieckus-Fries重排，阴离子Si→C烷基重排和Claisen-Schmidt缩合。该协议的适用性通过高效合成抗炎天然产物长果皮苷得到了证明。还提供了机制的见解。

  DOI：

  10.1021/acs.orglett.8b02269

文献信息

• Iodine-mediated direct synthesis of 3-iodoflavones
  作者：Avinash M. Patil、Dayanand A. Kamble、Pradeep D. Lokhande

  DOI：10.1080/00397911.2018.1440601

  日期：2018.6.3

  ABSTRACT Molecular iodine has been used for the regioselective, one pot, direct synthesis of 3-iodoflavones from 2′-allyloxy chalcones, 2′-hydroxy chalcones and flavones. Allyl deprotection, cyclization dehydrogenation and α-iodination of 2′-allyloxychalcones has been achieved in a single step to offer 3-iodoflavones. GRAPHICAL ABSTRACT

  摘要 分子碘已被用于区域选择性、一锅法、直接从 2'-烯丙氧基查耳酮、2'-羟基查耳酮和黄酮合成 3-碘黄酮。2'-烯丙氧基查耳酮的烯丙基脱保护、环化脱氢和 α-碘化已在一步中实现，以提供 3-碘黄酮。图形概要
• Flavonoids—38
  作者：Tamás Patonay、Rezsö Bognár、György Litkei

  DOI：10.1016/s0040-4020(01)83509-2

  日期：1984.1

  The reaction of 2'-hydroxychalcone dibromides 1 or α-bromo-2'-hydroxychalcones 15 with sodium azide resulted in a mixture of α-azido-2'-hydroxychalcones 2, 3-aryl-5-(2-hydroxy-pheny)isoxazoles 3, flavones 4, aurones 5 and 4-aryl-5-(2-hydroxybenzoyl)-1,2,3-triazoles 6. The product ratio was strongly influenced by the character of the substituent at position C-4. Similar results were obtained with 2

  2'-羟基查耳酮的二溴化物反应1或α-溴-2'- hydroxychalcones 15与叠氮化钠导致α叠氮基-2'- hydroxychalcones的混合物2，3-芳基-5-（2-羟基-苯基）异恶唑3，黄酮4，金酮5和4-芳基-5-（2-羟基苯甲酰基）-1,2,3-三唑6。产物比率受C-4位取代基的特性强烈影响。用2'-苄氧基-4-硝基查尔酮二溴化物（10）和2'-苄氧基-α-溴-4-硝基查尔酮（17）获得了相似的结果。讨论了通过α-溴查耳酮中间体将查尔酮二溴化物转化为产物的机理。
• Red fluorescence from tautomers of 2′-hydroxychalcones induced by intramolecular hydrogen atom transfer
  作者：Takeshi Teshima、Madoka Takeishi、Tatsuo Arai

  DOI：10.1039/b823431k

  日期：——

  Tautomer fluorescence in the longer wavelength region at 600 nm produced by intramolecular hydrogen atom transfer was observed in several 2′-hydroxychalcones having an electron donating group at the para position of the phenyl ring. The quantum yield of tautomer fluorescence increased by 1000 times upon decreasing the temperature from room temperature to 77 K. The introduction of dendritic substituents

  分子内在600 nm较长波长区域内的互变异构体荧光 氢在几个在苯环对位具有供电子基团的2'-羟基查耳酮中观察到原子转移。当将温度从室温降低到77 K时，互变异构体荧光的量子产率增加了1000倍。树枝状取代基的引入也增加了互变异构体荧光的强度。可以通过引入分子内来控制烯烃的光化学和光物理性质氢 键合和光诱导 氢 原子转移。
• Synthesis of Flavones through NaI‐Mediated Electrochemical Cyclization of Chalcones
  作者：Taweesak Gulchatchai、Thao Nguyen Thanh Huynh、Natthanan Vijara、Tanatorn Khotavivattana、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1002/ejoc.202300556

  日期：2023.9.21

  In this work, we demonstrated a novel electrochemical oxidative cyclization for synthesis of flavone from 2’-hydroxychalcone using an inexpensive using low toxic NaI as mediator/electrolyte without external additives in EtOH/water solvent. The key features of this reaction include its broad substrate scope, scalability, ability to operate with benign solvent at room temperature, and no requirement

  在这项工作中，我们展示了一种新型电化学氧化环化方法，用于从 2'-羟基查耳酮合成黄酮，使用廉价的低毒 NaI 作为介体/电解质，无需外部添加剂，在乙醇/水溶剂中。该反应的主要特点包括底物范围广泛、可扩展性、能够在室温下使用良性溶剂进行操作，并且不需要强氧化剂和外部添加剂。
• Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides:  3-Hydroxychromanones and -flavanones <i>versus</i> 2-(1-Hydroxyalkyl)-3-coumaranones
  作者：Tamás Patonay、Albert Lévai、Csaba Nemes、Tibor Timár、Gábor Tóth、Waldemar Adam

  DOI：10.1021/jo960163z

  日期：1996.1.1

  Competitive alpha and beta cyclization of 2'-hydroxychalcone epoxides affords 2-(alpha-hydroxybenzyl)-3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2'-hydroxychalcones by dimethyldioxirane followed by either base- or acid-catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for alpha cyclization was observed in the case of beta-unsubstituted or -monoalkylated alpha,beta-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the beta,beta-dimethylated substrates.