(E)-3-(2-hydroxy-4-methoxyphenyl)acrylaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-3-(2-hydroxy-4-methoxyphenyl)acrylaldehyde
• 英文别名: 3-(2-Hydroxy-4-methoxyphenyl)prop-2-enal；(E)-3-(2-hydroxy-4-methoxyphenyl)prop-2-enal
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: WMRKBFFUHNUAFH-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-hydroxy-4-methoxyphenyl)acrylaldehyde 在 (S)-2-(((叔丁基二甲基甲硅烷基)氧基)二苯基甲基)吡咯烷 、 苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 32.0h， 生成 (2'R,3S,5'S)-1-benzyl-8'-methoxy-5'H-spiro[indoline-3,4'-[2,5]methanobenzo[d][1,3]dioxepin]-2-one
  参考文献：
  名称：

  螺氧杂吲哚骨架的有机催化不对称合成缩醛

  摘要：

  已开发出第一个高度非对映体和对映体选择性合成包埋有螺硫辛多的桥连式O，O-缩醛的方法。在该方法中，使用二恶唑和2-羟基肉桂醛作为反应伙伴。通过二芳基脯氨醇TBS醚催化的迈克尔反应，然后与TFA缩醛形成，获得所需的产物。

  DOI：

  10.1021/acs.joc.8b02156
• 作为产物：
  描述：

  4-甲氧基水杨酸 、 甲酰甲撑基三苯基磷 以 甲苯 为溶剂， 反应 8.0h， 生成 (E)-3-(2-hydroxy-4-methoxyphenyl)acrylaldehyde
  参考文献：
  名称：

  基于肉桂醛的新型阿司匹林衍生物，用于治疗大肠癌

  摘要：

  大肠癌（CRC）是全球死亡的主要原因。当前CRC的治疗涉及抗癌剂，其具有相对良好的功效，但是非选择性地靶向癌细胞和非癌细胞。因此，需要发现和开发具有有效抗癌作用但显示出脱靶细胞作用降低的新型CRC疗法。在这里，设计和合成了一系列新的基于肉桂醛的阿司匹林衍生物。生物学评估表明活性最高的化合物1f与母体化合物相比，HCT-8细胞的抗增殖功效提高了10倍以上。它的作用在另一种CRC细胞系DLD-1中也得到了类似的再现，但在非致瘤性结肠细胞中的抑制活性却降低了7至11倍。流式细胞仪分析显示1f诱导的细胞周期停滞和凋亡，并通过免疫印迹分析裂解的caspase 3和PARP的相对蛋白水平以及CRC细胞中的ROS产生来进一步验证。更重要的是，1f在小鼠异种移植模型中显着抑制了体内植入的CRC的生长。综上所述，我们的结果表明，基于肉桂醛的阿司匹林衍生物，例如1f 有望作为新型抗CRC药物用于进一步的药物开发。

  DOI：

  10.1016/j.bmcl.2018.07.032

文献信息

• A Bioinspired Cascade Sequence Enables Facile Assembly of Methanodibenzo[<i>b</i>,<i>f</i>][1,5]dioxocin Flavonoid Scaffold
  作者：Hongxin Liu、Yu Wang、Xueying Guo、Luqiong Huo、Zhifang Xu、Weimin Zhang、Shengxiang Qiu、Bao Yang、Haibo Tan

  DOI：10.1021/acs.orglett.7b03630

  日期：2018.2.2

  A remarkable bioinspired EDDA-mediated method for the selective construction of biologically interesting and highly strained bridged methanodibenzo[b,f][1,5]dioxocin flavonoid scaffold was uncovered by starting from a variety of readily available acylphloroglucinol and 2-hydroxycinnamaldehyde substrates. This method merges a fascinating olefin isomerization/hemiacetallization/dehydration/[3 + 3]-type

  通过从各种容易获得的酰基间苯三酚和2-羟基肉桂醛底物开始，发现了一种出色的受生物启发的EDDA介导的方法，该方法可选择性地构建生物学上有趣的高桥连的甲烷二苯并[ b，f ] [1,5]二恶英类黄酮支架。该方法合并了一个迷人的烯烃异构化/半缩醛化/脱水/ [3 + 3]型环加成级联反应，该反应由原位生成的铬鎓中间体驱动，为有效地获得此类类黄酮类似物提供了方便且可行的合成策略。
• Formal carbene insertion into C O double bond: A facile approach to the synthesis of 2H-chromenes
  作者：Mingfeng Li、Rui Chu、Yun Zhao、Wenhao Hu、Shunying Liu

  DOI：10.1016/j.tet.2018.07.001

  日期：2018.8

  A formal carbene insertion into CO double bonds of 2-hydroxycinnamaldehydes catalyzed by Rh2(esp)2 with Na2CO3 as additive has been disclosed by using aryldiazoacetates as carbene precursors. 2H-chromenes with a quaternary carbon at C-2 position were readily obtained from simple starting materials in good yields with excellent diastereoselectivity under mild reaction conditions in one pot. The reaction

  通过使用芳基重氮乙酸酯作为卡宾前体，已经公开了通过Rh 2（esp）2与Na 2 CO 3作为添加剂催化的2-羟基肉桂醛在C O双键中的正式卡宾插入。在一个罐中，在温和的反应条件下，可以容易地从简单的起始原料以高收率和优异的非对映选择性获得具有在C-2位置具有季碳的2 H-色烯。研究了反应机理，并提出了由Rh（II）相关的卡宾和（E）-2-羟基肉桂醛形成环氧化物中间体的方法，然后采用级联环氧化物开环方法，其中（E）-中间体转换为（Z）-中间体，得到（Z）-产物。
• Organocatalytic Asymmetric Cascade Reaction between<i>o</i>-Hydroxycinnamaldehydes and<i>γ</i>/<i>δ</i>-Hydroxyenones: A Route to Tetrahydrofuran/Tetrahydropyran-Fused 3,4-Dihydrocoumarins
  作者：Buddhadeb Mondal、Subhas Chandra Pan

  DOI：10.1002/adsc.201800900

  日期：2018.11.16

  developed via a cascade reaction between 2‐hydroxy cinnamaldehydes and γ/δ‐hydroxy enones followed by pyridinium chlorochromate oxidation. Diphenylprolinol silyl ether catalyst in combination with acetic acid was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst and the additive, the desired products were obtained in high enantio‐ and diastereoselectivities.

  通过2-羟基肉桂醛和γ / δ-羟基烯酮的级联反应，然后进行吡啶鎓氯代铬酸铬的氧化，开发了第一个有机催化不对称合成四氢呋喃/四氢吡喃稠合的3,4-二氢香豆素。发现二苯基脯氨醇甲硅烷基醚催化剂与乙酸结合对于级联反应是最有效的。用10摩尔％的催化剂和添加剂，可以得到高对映选择性和非对映选择性的所需产物。
• New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions
  作者：Marie-Elise Trân-Huu-Dâu、Rudolf Wartchow、Ekkehard Winterfeldt、Yung-Sing Wong

  DOI：10.1002/1521-3765(20010601)7:11<2349::aid-chem23490>3.0.co;2-c

  日期：2001.6.1

  A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some parameters which affect the reactivity in this high chiral discrimination process. In addition, the resulting [4+2] cycloadducts allowed the preparation of new polyfunctional cyclohexenone derivatives.
• Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues
  作者：Qingyong Li、Jian Chen、Shuyue Luo、Jialin Xu、Qiaoxian Huang、Tianyu Liu

  DOI：10.1016/j.ejmech.2015.02.005

  日期：2015.3

  In this study, 12 asymmetric curcumin (CUR) analogues and 5 symmetric curcumin derivatives were synthesized, the antioxidant activity of these derivatives were evaluated by radicals 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay, 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) assay, ROO center dot (TRAP) assay and O2-center dot (NET) assay and anti-proliferative activities of these analogues were assessed against the human hepatoma cell line (SMMC-7721), the human breast cancer cell line (MCF-7) and the human prostate cancer cell lines (PC-3). Most of the asymmetric compounds showed stronger antioxidant activities than Vitamin C (Vc). Curcumin analogues reducing free radicals contain two reaction mechanisms: H-atom and electron transfer mechanisms. Compound 14 showed the most significant antioxidant activity compared with curcumin and other derivatives. Shorted the carbon chain of 14 can reduce the O-H bond dissociation enthalpy (BED) to improve the antioxidant activity. The antioxidant activity of 25 was similar to curcumin. All of the compounds performed better in an anti-proliferate assay than curcumin, especially compound 25, which exhibited the preferential cytotoxic activity against MCF-7 cells(25, IC50 = 9.11 mu M, curcumin, IC50 = 70.2 mu M). Considering these data, future studies should be performed to assess the therapeutic values of these asymmetric curcumin analogues. (C) 2015 Elsevier Masson SAS. All rights reserved.