（E）-3-（2,4-二甲氧基苯基）丙烯酸乙酯 | 24393-63-3

• 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
• 中文名称: （E）-3-（2,4-二甲氧基苯基）丙烯酸乙酯
• 英文名称: ethyl 2,4-dimethoxycinnamate
• 英文别名: (E)-ethyl 3-(2,4-dimethoxyphenyl)acrylate；2-Propenoic acid, 3-(2,4-dimethoxyphenyl)-, ethyl ester, (E)-；ethyl (E)-3-(2,4-dimethoxyphenyl)prop-2-enoate
• CAS: 24393-63-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: FKXUHAPNEJNLCB-SOFGYWHQSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  184 °C(Press: 8 Torr)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

反应信息

• 作为反应物：
  描述：

  （E）-3-（2,4-二甲氧基苯基）丙烯酸乙酯 在 二异丁基氢化铝 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (E)-3-(2,4-dimethoxyphenyl)acrylaldehyde
  参考文献：
  名称：

  Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

  摘要：

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.059
• 作为产物：
  描述：

  2,4-二甲氧基苯甲醛 在 哌啶 、 吡啶 、 硫酸 作用下， 反应 5.0h， 生成 （E）-3-（2,4-二甲氧基苯基）丙烯酸乙酯
  参考文献：
  名称：

  Potapov, V. M.; Gracheva, R. A.; Sivov, N. A., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 9, p. 1694 - 1699

  摘要：

  DOI：

文献信息

• Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C–H Annulation and Their Application to Pd-Catalyzed Aerobic C–H Alkenylation
  作者：Hyun Tae Kim、Eunsu Kang、Minkyu Kim、Jung Min Joo

  DOI：10.1021/acs.orglett.1c01040

  日期：2021.5.7

  A new class of bidentate ligands was prepared by a modular approach involving Rh-catalyzed C–H annulation reactions. The resulting conformationally constrained ligands enabled the Pd-catalyzed C–H alkenylation at electron-rich and sterically less hindered positions of electron-rich arenes while promoting the facile oxidation of Pd(0) intermediates by oxygen. This newly introduced ligand class is complementary

  通过涉及Rh催化的C–H环化反应的模块化方法，制备了一类新的双齿配体。最终形成的构象受约束的配体使Pd催化的C-H链烯基在富电子和富电子芳烃的位置上受阻较小，同时促进了Pd（0）中间体容易被氧氧化。这种新引入的配体类别与为Pd催化的氧化反应开发的配体互补，并可能在过渡金属催化的反应中找到广泛的应用。
• Acid-labile anchor groups for the synthesis of peptide amides by a
  申请人：Hoechst Aktiengesellschaft

  公开号：US05124478A1

  公开（公告）日：1992-06-23

  The invention relates to new compounds of the formula ##STR1## in which R.sup.1 denotes (C.sub.1 -C.sub.8)-alkyl, R.sup.2 denotes an amino acid residue which is protected with a urethane protective group which can be eliminated with weak acid or base, or denotes an amino protective group which can be eliminated with weak acid or base, R.sup.3 denotes hydrogen or (C.sub.1 -C.sub.4)-alkyl, and Y.sup.1 -Y.sup.9 denote identical or different radicals hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or --O--(CH.sub.2).sub.n --COOH (with n=1 to 6), with one of these radicals being --O--(CH.sub.2).sub.n --COOH, or Y.sup.1, Y.sup.2 and Y.sup.5 -Y.sup.9 denote identical or different radicals hydrogen, (C.sub.1 -C.sub.4)-alkyl or (C.sub.1 -C.sub.4)-alkoxy, Y.sup.3 denotes hydrogen or (C.sub.1 -C.sub.8)-alkoxy and Y.sup.4 denotes --(CH.sub.2).sub.n --COOH or --NH--CO--(CH.sub.2).sub.n --COOH (with n=1 to 6). Processes for the preparation thereof and the synthesis of peptide amides by a solid-phase method using these new compounds (spacers) are described.

  该发明涉及公式##STR1##中的新化合物，其中R.sup.1表示(C.sub.1 -C.sub.8)-烷基，R.sup.2表示氨基酸残基，其用尿素保护基保护，可以用弱酸或碱消除，或表示可以用弱酸或碱消除的氨基保护基，R.sup.3表示氢或(C.sub.1 -C.sub.4)-烷基，Y.sup.1 -Y.sup.9表示相同或不同的基团氢，(C.sub.1 -C.sub.4)-烷基，(C.sub.1 -C.sub.4)-烷氧基或--O--(CH.sub.2).sub.n --COOH（n=1至6），其中其中一个基团为--O--(CH.sub.2).sub.n --COOH，或Y.sup.1、Y.sup.2和Y.sup.5 -Y.sup.9表示相同或不同的基团氢，(C.sub.1 -C.sub.4)-烷基或(C.sub.1 -C.sub.4)-烷氧基，Y.sup.3表示氢或(C.sub.1 -C.sub.8)-烷氧基，Y.sup.4表示--(CH.sub.2).sub.n --COOH或--NH--CO--(CH.sub.2).sub.n --COOH（n=1至6）。描述了制备这些化合物（间隔物）的方法以及使用这些新化合物（间隔物）通过固相法合成肽酰胺的方法。
• [EN] XANTHONE DERIVATIVES, UV PROTECTIVE COMPOSITION CONCENTRATE, METHOD OF PREPARATION OF UV PROTECTIVE COMPOSITION CONCENTRATE, USE OF UV PROTECTIVE COMPOSITION CONCENTRATE AND COSMETIC UV PROTECTIVE PRODUCT<br/>[FR] DÉRIVÉS DE XANTHONE, CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV, PROCÉDÉ DE PRÉPARATION DE CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV, UTILISATION D'UN CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV ET PRODUIT COSMÉTIQUE DE PROTECTION CONTRE LES UV
  申请人：UNIV JAGIELLONSKI

  公开号：WO2021215943A1

  公开（公告）日：2021-10-28

  The first object of the invention is a xanthone derivative described by formula (I) where R1 is a substituent selected from the group comprising: hydrogen or alkoxy group; R2 is a substituent selected from the group comprising methylcinnamoyl, phenylpenta-2,4- dienenitrile, cyanoethenylphenyl or cyanoethenylalkyl substituent, wherein the phenyl ring is substituted with R3 selected from the group consisting of: hydrogen, alkoxy substituent or halide atom. The second objection of the invention is a UV protective composition concentrate containing the xanthone derivative described by the formula (I). The third object of the invention is a method for the preparation of a UV protective composition concentrate. The next object of the invention is the use of a UV protective composition concentrate for the production of UV protective cosmetic products. Yet another object of the invention is a cosmetic UV protective product.

  该发明的第一个对象是一种黄酮衍生物，其化学式为（I），其中R1是从包括：氢或烷氧基的基团中选择的取代基；R2是从包括：甲基肉桂酰基、苯基戊-2,4-二烯腈基、氰基乙烯基苯基或氰基乙烯基取代基中选择的取代基，其中苯环与R3选择自包括：氢、烷氧基取代基或卤素原子的基团。该发明的第二个对象是一种含有上述化学式（I）所述黄酮衍生物的紫外线防护组合物浓缩物。该发明的第三个对象是一种制备紫外线防护组合物浓缩物的方法。该发明的下一个对象是利用紫外线防护组合物浓缩物生产紫外线防护化妆品产品。该发明的另一个对象是一种化妆用紫外线防护产品。
• S,O‐Ligand‐Promoted Pd‐Catalyzed C−H Olefination of Anisole Derivatives
  作者：Verena Sukowski、Wen‐Liang Jia、Rianne Diest、Manuela Borselen、M. Ángeles Fernández‐Ibáñez

  DOI：10.1002/ejoc.202100737

  日期：2021.8.6

  The C−H olefination of substituted anisole derivatives as limiting reagents has been realized by a Pd/S, O-ligand catalyst providing the olefinated products in good yields and site selectivities. The reaction proceeds under mild conditions with a broad range of substituted aryl ethers bearing both electron-donating and electron-withdrawing substituents.

  作为限制试剂的取代苯甲醚衍生物的 CH 烯化已通过 Pd/S、O-配体催化剂实现，以良好的产率和位点选择性提供烯化产物。该反应在温和条件下进行，具有广泛的取代芳基醚，带有给电子和吸电子取代基。
• Regioselective Synthesis of Linear and Angular Pyridazine Furocoumarins
  作者：Eugenio Uriarte、José González-Gómez、Lourdes Santana

  DOI：10.1055/s-2002-19292

  日期：——

  With a view to develop a general regioselective route to pyridazine analogues of benzofurocoumarins, the angular compound 3 and the linear compound 9 were synthesized. In both cases the key step in the construction of the fused pyridazine ring was a Diels-Alder reaction of the intermediate dihydrofura-3-ones with 3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine. The furocoumarinone precursor 2 of compound 3 was synthesized in 60% yield by regioselective Fries rearrangement of 7-(chloroacetyloxy)coumarin (1). The benzofuranone 7, the precursor of compound 9, was obtained in a preparatively useful scale and 34% overall yield from ethyl 2,4-dimethoxycinnamate (4) in 3 steps by regioselective Friedel-Crafts chloroacetylation and further cyclization. The coumarin skeleton of compound 9 was completed in the final step by lactonization with BBr3.

  为了开发苯并呋喃香豆素哒嗪类似物的一般区域选择性路线，我们合成了角状化合物 3 和线状化合物 9。在这两种情况下，构建融合哒嗪环的关键步骤都是中间体二氢呋喃-3-酮与 3,6-双（三氟甲基）-1,2,4,5-四嗪的 Diels-Alder 反应。化合物 3 的呋喃香豆酮前体 2 是通过 7-（氯乙酰氧基）香豆素（1）的区域选择性弗里斯重排合成的，收率为 60%。化合物 9 的前体苯并呋喃酮 7 是以 2,4-二甲氧基肉桂酸乙酯（4）为原料，通过区域选择性弗里德尔-卡夫斯氯乙酰化反应和进一步环化反应，分三步制备得到的，总收率为 34%。化合物 9 的香豆素骨架在最后一步通过 BBr3 内酯化完成。