4-(4-hydroxy-3-methoxy-5-nitrophenyl)buten-2-one | 124946-66-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(4-hydroxy-3-methoxy-5-nitrophenyl)buten-2-one
• 英文别名: 1t-(5-nitro-4-hydroxy-3-methoxy-phenyl)-buten-(1)-one-(3)；1t-(5-Nitro-4-hydroxy-3-methoxy-phenyl)-buten-(1)-on-(3)；4-(4-Hydroxy-3-methoxy-5-nitrophenyl)but-3-en-2-one；(E)-4-(4-hydroxy-3-methoxy-5-nitrophenyl)but-3-en-2-one
• CAS: 124946-66-3
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: VDCIGANJFRZNOV-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二茂铁甲醛 、 4-(4-hydroxy-3-methoxy-5-nitrophenyl)buten-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以67%的产率得到(1E,4E)-1-ferrocenyl-5-(4-hydroxy-3-methoxy-5-nitrophenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives: Which possesses the highest activity to protect DNA or scavenge radical?

  摘要：

  A series of asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives were synthesized. Their antioxidant abilities in protecting DNA against 2,2'-azobis(2-amidinopropane hydrochloride)-induced oxidation and scavenging 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS) radical were evaluated. In synthesis, the Michael addition reactions between phenylhydrazine and asymmetrical ferrocenylidene curcumin derivatives exhibit evident regioselectivity. The direction of addition depends on whether the benzene ring is substituted or not. The antioxidant abilities of compounds will increase when the ferrocenyl group is introduced. Moreover, such improvement derived from ferrocenyl group is also related to other substituent groups in molecule, not independent. Interestingly, p-dimethylamino group which is never considered as an active group, however, exhibits the best activity in protecting DNA and scavenging ABTS radical.

  DOI：

  10.1007/s00044-014-0924-1
• 作为产物：
  描述：

  5-硝基香兰素 在 sodium hydroxide 、 丙酮 作用下， 生成 4-(4-hydroxy-3-methoxy-5-nitrophenyl)buten-2-one
  参考文献：
  名称：

  EFFECT OF SUBSTITUENTS IN CERTAIN CONDENSATIONS OF BENZALDEHYDE

  摘要：

  DOI：

  10.1021/ja01342a035

文献信息

• Berlin; Scherlin; Serebrennikowa, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 569,575
  作者：Berlin、Scherlin、Serebrennikowa

  DOI：——

  日期：——
• Rajakumar; Rao, Pharmazie, 1994, vol. 49, # 7, p. 516 - 519
  作者：Rajakumar、Rao

  DOI：——

  日期：——
• FORMATION OF PYRAZOLINES FROM UNSYMMETRICALLY SUBSTITUTED DIBENZALACETONES
  作者：L. CHAS. RAIFORD、RALPH H. MANLEY

  DOI：10.1021/jo01212a004

  日期：1940.11
• EFFECT OF SUBSTITUENTS IN CERTAIN CONDENSATIONS OF BENZALDEHYDE
  作者：L. Chas. Raiford、William F. Talbot

  DOI：10.1021/ja01342a035

  日期：1932.3
• Asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives: Which possesses the highest activity to protect DNA or scavenge radical?
  作者：Pei-Ze Li、Zai-Qun Liu

  DOI：10.1007/s00044-014-0924-1

  日期：2014.7

  A series of asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives were synthesized. Their antioxidant abilities in protecting DNA against 2,2'-azobis(2-amidinopropane hydrochloride)-induced oxidation and scavenging 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS) radical were evaluated. In synthesis, the Michael addition reactions between phenylhydrazine and asymmetrical ferrocenylidene curcumin derivatives exhibit evident regioselectivity. The direction of addition depends on whether the benzene ring is substituted or not. The antioxidant abilities of compounds will increase when the ferrocenyl group is introduced. Moreover, such improvement derived from ferrocenyl group is also related to other substituent groups in molecule, not independent. Interestingly, p-dimethylamino group which is never considered as an active group, however, exhibits the best activity in protecting DNA and scavenging ABTS radical.