3-(3-氰基苯基)丙烯酸乙酯 | 55197-33-6

• 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: 3-(3-氰基苯基)丙烯酸乙酯
• 英文名称: Ethyl 3-(3-cyanophenyl) acrylate
• 英文别名: Ethyl 3-(3-cyanophenyl)-2-propenoate；ethyl 3-(3-cyanophenyl)prop-2-enoate
• CAS: 55197-33-6
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: KCHOZJMCISWKHW-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-氰基苯基)丙烯酸乙酯 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 生成 3-(3-氰基苯基)丙酸乙酯
  参考文献：
  名称：

  Inhibition of uridine phosphorylase: synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils.

  摘要：

  A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine-induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 mu M), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3-alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC(50)s of 0.047 and 0.027 mu M, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 mu M.

  DOI：

  10.1021/jm00019a015
• 作为产物：
  描述：

  间溴苯甲腈 、 丙烯酸乙酯 在 3-(2-hydroxyethyl)-1-((1-(2-hydroxyethyl)pyridin-1-ium-3-yl)methyl)-1H-imidazolium bromide 、 三乙胺 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到3-(3-氰基苯基)丙烯酸乙酯
  参考文献：
  名称：

  柔性的咪唑鎓盐，可在好氧条件下原位应用在钯催化的丙烯酸酯的Mizoroki-Heck偶联反应中

  摘要：

  新的不对称N，N的合成，表征及原位催化性能描述了在好氧条件下丙烯酸酯与芳基溴化物在咪唑罗基-赫克偶联过程中基于二氮杂咪唑的二元盐。合成了一系列具有可变的空间和电子特性的柔性二羧酸盐，收率良好。使用光谱技术可以很好地表征所有盐。X射线衍射分析具有相同的双主链和不同的抗衡阴离子的两种盐表明，配体采用两种不同的构象，这些构象受阴离子的性质影响。因此，配体由于其柔性性质而能够根据环境变化而改变其构象。发现所有合成的咪唑鎓盐均在原位具有活性有氧条件下钯催化的米佐罗基-赫克偶联。在这些盐中，结合了双齿螯合O，O配体和卡宾的特征的羟基官能化咪唑鎓盐显示出最大的催化活性。使用这些咪唑鎓盐作为预配体合成了各种肉桂酸的芳基和杂芳基甲基和乙基酯。此外，NMR研究证实原位生成正常N咪唑-2-亚烷基环的C-2位的杂环卡宾。还进行了汞中毒测试，以确定具有催化活性的钯物质的性质。有氧条件，低催化负载量（0.5 mol％

  DOI：

  10.1002/aoc.3503

文献信息

• Factor xa inhibitors with aryl-amidines and derivatives, and prodrugs thereof
  申请人：——

  公开号：US20030065176A1

  公开（公告）日：2003-04-03

  The present invention relates to a compound with aryl-amidines, particularly amidinoaryl-cyclopropanes, amidinoarylmethyl-pyrroles, amidinoaryl-benzenes, amidinoaryl-pyridines, or amindonoaryl-alanines, represented by formula (1), a pharmaceutically acceptable salt, a prodrug, a hydrate, a solvate or an isomer thereof, which are inhibitors of coagulation enzyme, factor Xa (FXa). The present invention also relates to a pharmaceutical composition containing the compound, and a method of using the same as an anticoagulant agent for treatment and prevention of thrombosis disorders.

  本发明涉及一种具有芳基胺基的化合物，特别是表示为式（1）的芳基胺基环丙烷，芳基胺基甲基吡咯烷，芳基胺基苯，芳基胺基吡啶或芳基胺基丙氨酸的化合物，其为凝血酶Xa（FXa）的抑制剂，包括药用盐、前药、水合物、溶剂合物或其异构体。本发明还涉及含有该化合物的药物组合物，以及将其用作抗凝血剂治疗和预防血栓症障碍的方法。
• Facile and Convenient Method of Deuterium Gas Generation Using a Pd/C-Catalyzed H2–D2 Exchange Reaction and Its Application to Synthesis of Deuterium-Labeled Compounds
  作者：Takanori Kurita、Fumiyo Aoki、Takuto Mizumoto、Toshihide Maejima、Hiroyoshi Esaki、Tomohiro Maegawa、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/chem.200701245

  日期：2008.4.7

  The Pd/C-catalyzed H(2)-D(2) exchange reaction using a H(2)-D(2)O combination provided a general, efficient and environmentally friendly route for the preparation of deuterium gas (D(2)). H(2) sealed in a reaction flask was converted into nearly pure D(2), which could be used for the Pd/C-catalyzed one-pot reductive deuteration of various reducible functionalities and the chemoselective one-pot deuterogenation

  使用H（2）-D（2）O组合的Pd / C催化的H（2）-D（2）交换反应为制备氘气（D（2） ）。密封在反应烧瓶中的H（2）转化为几乎纯净的D（2），可用于Pd / C催化的各种还原功能的一锅还原氘代和烯烃和乙炔的化学选择性一锅氘代。此外，我们建立了在气球中捕获D（2）的捕获方法，该方法已成功地应用于腈作为烷基化试剂的伯胺的Pd / C催化的还原性单-N-烷基化反应。
• REGIOSELECTIVITY OF THE METHYL-TOSMIC REACTION WITH SUBSTITUTED ETHYL CINNAMATES
  作者：Roberto Di Santo、Roberta Costi、Carlo Galeffi、Michela Forte

  DOI：10.1080/00304940509354884

  日期：2005.4

  with the above mentioned olefin derivative^.'.^-^ Our decade-long interest in the chemistry of pyrrole annulated heterocyclic systems led us to explore new routes to synthesize 2H-pyrrolo[3,4-c]quinoline derivatives, with the aim to obtain new potential ligands of the 5-HT receptors. A recent papers reported the synthesis of 1 substituted 2H-pyrrolo[3,4-c]quinolines via the Me-TosMIC reaction with ethyl

  甲苯磺酰甲基异氰化物 (TosMIC) 是一种有吸引力的结构单元，可用于合成环酮、腈、胺，尤其是杂环合成。具有与吸电子基团共轭的碳碳双键的物质，如羰基、腈和硝基，已广泛用于使用金属化甲苯磺酰甲基异氰化物合成 3,4-二取代吡咯。1-4 此外，通过 a-单取代的 TosMIC 与上述烯烃衍生物反应获得 2,3,4-三取代的吡咯^.'.^-^ 我们对吡咯环状杂环系统化学的长达十年的兴趣使我们探索合成2H-吡咯并[3,4-c]喹啉衍生物的新途径，以期获得5-HT受体新的潜在配体。最近的一篇论文报道了通过 Me-TosMIC 与肉桂酸乙酯的反应合成 1 取代的 2H-吡咯并 [3,4-c] 喹啉。令人惊讶的是，2-硝基肉桂酸乙酯与 Me-TosMIC 的反应旨在获得关键中间体 2-甲基-3-(2-硝基苯基)1H-吡咯-4-羧酸乙酯 (2a)，得到预期的 2a 和其异构体 2-甲基-4-(2-硝基苯
• Influence of Non-Covalent Interactions in the <i>Exo</i>- and Regioselectivity of Aza-Diels–Alder Reactions: Experimental and DFT Calculations
  作者：Sebastián Gallardo-Fuentes、Nicolás Lezana、Susan Lühr、Antonio Galdámez、Marcelo Vilches-Herrera

  DOI：10.1021/acs.joc.9b01390

  日期：2019.9.6

  A systematic experimental and theoretical study of the intermolecular Aza-Diels-Alder reaction using 5-aminopyrrole as a building block shows that the commonly accepted endo selectivity, ruled by controversial secondary orbital interactions, are overcome by non-covalent interactions affording to the unusual exo adduct. Additionally, the regioselectivity is also influenced for such interactions. The starting materials are easily prepared, and the use of water as the solvent is a great achievement for the development of cleaner synthetic methodologies.
• Inhibition of uridine phosphorylase: synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils.
  作者：G. Faye Orr、David L. Musso、G. Evan Boswell、James L. Kelley、Suzanne S. Joyner、Stephen T. Davis、David P. Baccanari

  DOI：10.1021/jm00019a015

  日期：1995.9

  A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine-induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 mu M), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3-alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC(50)s of 0.047 and 0.027 mu M, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 mu M.