2-acetyl-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester

• 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: 2-acetyl-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester
• 英文别名: ethyl 2-(4-hydroxy-3-methoxybenzylidene)-3-oxo-butanoate；ethyl 2-(p-hydroxy-m-methoxybenzylidene)-3-oxobutanoate；ethyl-α-acetyl-3-methoxy-4-hydroxy cinnamate；Ethyl-alpha-acetyl-3-methoxy-4-hydroxy-cinnamate；ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-oxobutanoate
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: AEJYTNZPJSBVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(bromomethyl)-6-chloroquinolin-2(1H)-one 、 2-acetyl-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 2-[[4-[(6-chloro-1,2-dihydro-2-oxoquinolin-4-yl)methoxy]-3-methoxyphenyl]methylene]-3-oxobutanoic acid ethyl ester
  参考文献：
  名称：

  新型喹啉酮丙烯酸乙酯的合成及生物学研究

  摘要：

  摘要从4-（溴甲基）喹啉酮合成了一系列新的喹啉酮丙烯酸乙酯，并筛选了其体外抗菌和体内止痛和消炎活性。与非卤代喹啉酮和带有CH 3的喹啉酮相比，大多数在喹啉酮部分的C-6或C-7位置具有氯取代基且在芳氧基部分具有甲氧基的化合物具有较强的抗菌和抗真菌活性。在C-8位置 在药理学评估中，与简单的未取代（未卤代）喹啉酮相比，发现喹啉酮中C-6或C-7位置的卤素取代增强了该分子的镇痛和抗炎活性。通过元素分析，IR，1 H NMR，13 C NMR和FAB-MS对所有新合成化合物的结构进行了表征。 图形概要

  DOI：

  10.1007/s00706-011-0692-2
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 香草醛 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以68%的产率得到2-acetyl-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester
  参考文献：
  名称：

  以AlCl 3为催化剂，由β-二酮和醛轻松合成三取代烯烃

  摘要：

  研究了以氯化铝为催化剂由低活性β-二酮和醛制备三取代烯烃的方法。第一次使用常用的催化剂AlCl 3来促进这种冷凝。该方法是一种方便，低毒，高效的高产率工业合成三取代烯烃的方法。

  DOI：

  10.1007/s11164-011-0322-y

文献信息

• Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives
  作者：Mihaela-Anca Constantin、Jürgen Conrad、Uwe Beifuss

  DOI：10.1039/c2gc35848d

  日期：——

  The laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives using aerial oxygen as the oxidant has been developed. Depending on the substitution pattern of the vanillidene double bond of the substrate, either dilactones, dihydrobenzo[b]furans or biphenyls are formed.

  已经开发了使用空气中的氧作为氧化剂的漆酶催化的香草醛衍生物的氧化酚偶联。取决于底物的香兰素双键的取代方式，双内酯，二氢苯并[ b ]呋喃或联苯 形成。
• Photo stable organic sunscreen compositions
  申请人：EMD CHEMICALS, INC.

  公开号：US20040247536A1

  公开（公告）日：2004-12-09

  Photostable broad-spectrum organic sunscreen compositions comprising a UV-A sunscreen, such as Avobenzone, a photostabilizer, a UV-B liquid organic sunscreen, and a solubilizer and further enhancing the photostability by encapsulation using a sol-gel process.

  具有光稳定性的广谱有机防晒霜组合物包括UV-A防晒霜，如阿伏苯宗，光稳定剂，UV-B液体有机防晒霜，溶解剂，并通过溶胶-凝胶过程进行封装以进一步增强光稳定性。
• PHOTO STABLE ORGANIC SUNSCREEN COMPOUNDS WITH ANTIOXIDANT PROPERTIES AND COMPOSITIONS OBTAINED THEREFROM
  申请人：EM Industries

  公开号：US20030157035A1

  公开（公告）日：2003-08-21

  A compound of formula I 1 wherein A is a moiety which provides UV absorbing activity to the compound of formula I that comprises 1 divalent group or 2 monovalent groups, with at least one group having carbonyl (C═O) functionality. R 6 is linear or branched C 1 -C 8 alkyl and R 5 is a linear or branched C 1 -C 8 alkyl or hydrogen. Sunscreen formulations which contain these compounds and methods for using these compounds to prepare formulations are also provided.

  化合物I1的化学式为：其中A是一种基团，能够提供紫外线吸收活性给化合物I，它包括1个二价基团或2个一价基团，至少有一个基团具有羰基（C═O）功能。R6是线性或支链状的C1-C8烷基，而R5是线性或支链状的C1-C8烷基或氢。此外，还提供了含有这些化合物的防晒配方和使用这些化合物制备配方的方法。
• Photostable organic sunscreen composition
  申请人：Chaudhuri Ratan

  公开号：US20070059258A1

  公开（公告）日：2007-03-15

  The present invention relates to a sunscreen capsule comprising i) at least one UV-A organic sunscreen and ii) at least one photostabilizer; furthermore it relates to a composition for topical application comprising these capsule and methods of production and use of these capsules and compositions.

  本发明涉及一种含有i) 至少一种UV-A有机防晒剂和ii) 至少一种光稳定剂的防晒胶囊；此外，本发明还涉及一种含有这些胶囊的局部应用组合物，以及这些胶囊和组合物的生产和使用方法。
• Feruloylacetone as the model compound of half-curcumin: Synthesis and antioxidant properties
  作者：Jian-Ying Feng、Zai-Qun Liu

  DOI：10.1016/j.ejmech.2011.01.039

  日期：2011.4

  In order to clarify the contribution of phenolic and enolic hydroxyl group to the antioxidant capacity of feruloylacetone, a model compound of half-curcumin, 6-(p-hydroxy-m-methoxyphenyl)-5-hexene-2,4-dione (FT), 6-(p-benzyloxy-m-methoxyphenyl)-5-hexene-2,4-dione (BMFT), 6-(m,p-dihydroxyphenyl)-5-hexene-2,4-dione (DDFT), 6-(p-hydroxy-m-methoxyphenyl)hexane-2,4-dione (DHFT), 6-(p-hydroxy-m-methoxyphenyl)-5-hexene-2,4-diol (THFT), and ethyl 2-(p-hydroxy-m-methoxybenzylidene)-3-oxobutanoate (EOFT) were synthesized. The radical-scavenging abilities of these compounds were tested by trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+center dot)), 2,2'-diphenyl-1-picrylhydrazyl (DPPH), and galvinoxyl radicals. The reductive capacities were screened by quenching singlet oxygen and by inhibiting the oxidation of linoleic acid. They were also employed to inhibit the oxidation of DNA mediated by hydroxyl radical and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). In addition, they were applied to protect erythrocytes against AAPH- and hemin-induced hemolysis. The obtained results revealed that the antioxidant capacity of half-curcumin was derived from the phenolic-OH and the conjugated linkage between phenolic and enolic-OH. The enolic-OH itself cannot trap radicals. (C) 2011 Elsevier Masson SAS. All rights reserved.