(E)-1-(2-hydroxy-5-nitrophenyl)-3-phenylprop-2-en-1-one | 35234-45-8

• 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-hydroxy-5-nitrophenyl)-3-phenylprop-2-en-1-one
• CAS: 35234-45-8
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: TYZOYHUZLDIJJN-SOFGYWHQSA-N

物化性质

• 熔点：
  123-150 °C
• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxy-5-nitrophenyl)-3-phenylprop-2-en-1-one 在 溴 作用下， 以 吡啶 为溶剂， 生成 2,3-Dibromo-1-(2-hydroxy-5-nitro-phenyl)-3-phenyl-propan-1-one
  参考文献：
  名称：

  Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor

  摘要：

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00343-0
• 作为产物：
  描述：

  4-硝基苯基乙酸酯 在 sodium hydroxide 、 三氯化铝 、 硝基苯 作用下， 生成 (E)-1-(2-hydroxy-5-nitrophenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Szell, Chemische Berichte, 1958, vol. 91, p. 2609,2612

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed C–H Activation of Salicylaldehyde and Decarboxylative Coupling of Alkynoic Acids for the Selective Synthesis of Homoisoflavonoids and Flavones
  作者：Gabriel Charles Edwin Raja、Ji Yeon Ryu、Junseong Lee、Sunwoo Lee

  DOI：10.1021/acs.orglett.7b03325

  日期：2017.12.15

  Homoisoflavonoids were formed in DMSO exclusively, and flavones were formed in t-AmOH when salicylaldehyde and alkynoic acids reacted with [Ru(p-cymene)Cl2]2 and CsOAc. They were formed through C–H activation of salicylaldehyde and decarboxylative coupling of alkynoic acid. This reaction system showed good yields, broad substrate scope, and good functional group tolerance. It was found that chalcone

  当水杨醛和炔酸与[Ru（p- cymene）Cl 2 ] 2和CsOAc反应时，仅在DMSO中形成同黄酮，在t- AmOH中形成黄酮。它们是通过水杨醛的C–H活化和炔酸的脱羧偶联而形成的。该反应体系显示出良好的收率，广泛的底物范围和良好的官能团耐受性。发现查耳酮是均异黄酮和黄酮形成的中间体。
• Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/<i>oxa</i>-Michael Addition between Propargylamines with Water
  作者：Xinwei He、Mengqing Xie、Ruxue Li、Pui Ying Choy、Qiang Tang、Yongjia Shang、Fuk Yee Kwong

  DOI：10.1021/acs.orglett.0c01357

  日期：2020.6.5

  DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne–allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones

  已经开发了一种DBU催化的炔丙胺和水的一锅级联反应，用于合成黄烷酮。该过程是通过依次将水以1,4-共轭加成到炔基邻苯二甲酰甲基甲烷（o -AQM）上，然后进行炔烃-丙二烯异构化和随后的分子内氧杂-Michael加成反应。该策略提供了一种方便的方法，可以以良好的产率获得具有良好的官能团耐受性的宽泛的黄烷酮，特别是反应性卤素官能团。
• Flavone formation in the wheeler aurone synthesis
  作者：John A. Donnelly、Clement L. Higginbotham

  DOI：10.1016/s0040-4020(01)87902-3

  日期：1990.1

  bromomethylation of the side-chain of 2'-acetoxychalcones were found to produce minor quantities of flavones as well as the major product aurones when cyclized by aqueous ethanolic sodium hydroxide. The yields of flavone increased with increasing base concentration. The optimum concentration of hydroxide for aurone formation was below 1%. Greatly diminished yields of O-heterocycles were obtained when a nitro substituent

  发现当被氢氧化乙醇水溶液环化时，通过2'-乙酰氧基查耳酮的侧链的溴甲基化形成的二氢查耳酮产生少量的黄酮以及主要的产品金酮。黄酮类化合物的产率随碱浓度的增加而增加。用于形成金酮的氢氧化物的最佳浓度低于1％。当在环化2'-氧官能团的对面引入硝基取代基时，会大大降低O-杂环的收率。
• Reichel; Hempel, Justus Liebigs Annalen der Chemie, 1959, vol. 625, p. 184,193
  作者：Reichel、Hempel

  DOI：——

  日期：——
• Chhaya et al., Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1957, vol. 25/5 A, p. 8,11
  作者：Chhaya et al.

  DOI：——

  日期：——