4-烯丙基-2,6-二甲氧基乙酸苯酯 | 29540-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 4-烯丙基-2,6-二甲氧基乙酸苯酯
• 英文名称: 4-allyl-2,6-dimethoxyphenyl acetate
• 英文别名: (2,6-dimethoxy-4-prop-2-enylphenyl) acetate
• CAS: 29540-11-2
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: FDYLVSINANJYBC-UHFFFAOYSA-N

物化性质

• 熔点：
  43-44 °C
• 沸点：
  287.9±40.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)
• 保留指数：
  1737.5

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  4-烯丙基-2,6-二甲氧基乙酸苯酯 在 sodium hydroxide 、 乙醇 、 colloid 、 钯 作用下， 生成 4-丙基-2,6-二甲氧基苯酚
  参考文献：
  名称：

  Mauthner, Journal fur praktische Chemie (Leipzig 1954), 1921, vol. <2> 102, p. 42

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二甲氧基-1-(烯丙氧基)苯 在 溶剂黄146 作用下， 生成 4-烯丙基-2,6-二甲氧基乙酸苯酯
  参考文献：
  名称：

  Mauthner, Journal fur praktische Chemie (Leipzig 1954), 1921, vol. <2> 102, p. 42

  摘要：

  DOI：

文献信息

• DDQ-Mediated Oxidation of Allylarenes: Expedient Access to Cinnamaldehyde-Containing Phenylpropanoids
  作者：Tao-Shan Jiang、Yongping Cai、Qingqing Zhang、Guohui Li、Xi Cheng

  DOI：10.1055/s-0037-1609554

  日期：2018.12

  Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization–ring-closing-metathesis strategy.

  含有肉桂醛基团的苯丙烯类天然产物可以通过2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）氧化介导的烯丙基芳烃轻松合成。本文描述的代表性示例包括来自单木质素生物合成的五种4-羟基肉桂醛衍生物、来自植物提取物的Boropinal C和7-甲氧基乌太呋醛。特别是，通过选择性单氧化和随后的异构化-环闭合-鲁米诺烯交换策略，实现了对7-甲氧基乌太呋醛的简单合成。
• NO-Donor Phenols:  A New Class of Products Endowed with Antioxidant and Vasodilator Properties
  作者：Donatella Boschi、Gian Cesare Tron、Loretta Lazzarato、Konstantin Chegaev、Clara Cena、Antonella Di Stilo、Marta Giorgis、Massimo Bertinaria、Roberta Fruttero、Alberto Gasco

  DOI：10.1021/jm0510530

  日期：2006.5.1

  The synthesis and study of the antioxidant and vasodilator properties of a new class of phenols able to release nitric oxide are described. The products were designed through a symbiotic approach using selected phenols and selected nitrooxy and furoxan NO-donors as reference models. The antioxidant activities of the hybrid products were assessed by detecting the 2-thiobarbituric acid reactive substances

  描述了新型能够释放一氧化氮的酚类的抗氧化剂和血管扩张剂的合成和研究。这些产品是通过共生方法设计的，使用了选定的苯酚以及选定的硝基氧基和呋喃喃NO供体作为参考模型。通过检测在大鼠肝细胞的微粒体膜中存在的亚铁盐/抗坏血酸诱导的脂质的自氧化中产生的2-硫代巴比妥酸反应性物质（TBARS），可以评估杂化产物的抗氧化活性。在与去氧肾上腺素预收缩的大鼠主动脉条上评估血管舒张活性。一些产品（13、35、37、60-62、64）主要表现为血管扩张剂，而其他产品则表现为抗氧化剂（24、32、72），并且两种特性在19、41和68中相对平衡。
• Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1&amp;prime;&lt;em&gt;S&lt;/em&gt;-1&amp;prime;-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells
  作者：Su Ki Liew、Mohamad Nurul Azmi、Lionel L.A. In、Khalijah Awang、Noor Hasima Nagoor

  DOI：10.2147/dddt.s130349

  日期：——

  Nine analogs of 1' S-1'-acetoxychavicol acetate (ACA) were hemi-synthesized and evaluated for their anticancer activities against seven human cancer cell lines. The aim of this study was to investigate the anti-proliferative, apoptotic, and anti-migration effects of these compounds and to explore the plausible underlying mechanisms of action. We found that ACA and all nine analogs were non toxic to human mammary epithelial cells (HMECs) used as normal control cells, and only ACA, 1'-acetoxyeugenol acetate (AEA), and 1'-acetoxy-3,5-dimethoxychavicol acetate (AMCA) inhibited the growth of MDA-MB-231 breast cancer cells with a half-maximal inhibitory concentration (IC50) value of <30.0 mu M based on 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay results, and were selected for further investigation. DNA fragmentation assays showed that these three compounds markedly induced apoptosis of MDA-MB-231 cells. Western blot analysis revealed increased expression levels of cleaved PARP, p53, and Bax, while decreased expression levels of Bcl-2 and Bcl-xL were seen after treatment, indicating that apoptosis was induced via the mitochondrial pathway. Moreover, ACA, AEA, and AMCA effectively inhibited the migration of MDA-MB-231 cells. They also downregulated the expression levels of pFAK/FAK and pAkt/Akt via the integrin beta 1-mediated signaling pathway. Collectively, ACA and its hemi-synthetic analogs, AEA and AMCA are seen as potential anticancer agents following their abilities to suppress growth, induce apoptosis, and inhibit migration of breast cancer cells.