2-cyano-3-(2-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-cyano-3-(2-methoxyphenyl)acrylic acid ethyl ester
• 英文别名: <2-Methoxy-benzyliden>-cyan-essigsaeure-ethylester；2-Cyano-3-(2-methoxy-phenyl)-acrylic acid ethyl ester；ethyl 2-cyano-3-(2-methoxyphenyl)prop-2-enoate
• 化学式: C₁₃H₁₃NO₃
• mdl: MFCD00175267
• 分子量: 231.251
• InChiKey: LXZSBCQFZFCBFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-3-(2-methoxyphenyl)acrylic acid ethyl ester 在 5percent Pd/C 盐酸 、 sodium tetrahydroborate 、 PPA 、 硫酸 、 叠氮磷酸二苯酯 、 氢气 、 碘 、 sodium hydride 、 magnesium 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、241.32 kPa 条件下， 反应 34.5h， 生成 [3-(3,4-dichlorophenyl)-4-methoxyindan-1-yl]methylamine
  参考文献：
  名称：

  Design, Synthesis, and Monoamine Transporter Binding Site Affinities of Methoxy Derivatives of Indatraline

  摘要：

  A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline affected its affinity and selectivity greatly. Except for the 4-methoxy derivative 13a,which had the same high affinity at the dopamine transporter binding site as indatraline, the other methoxy-containing analogues (13b-f and 17) exhibited lower affinity than indatraline for the three transporter binding sites. However, some of the analogues were more selective than indatraline, and the B-methoxy derivative 13c displayed the highest affinity for both the serotonin and norepinephrine transporters. This compound retained reasonable affinity for the dopamine transporter and is a promising template for the development of a long-acting inhibitor of monoamine transporters. Such inhibitors have potential as medications for treatment, as a substitution medication, or for prevention of the abuse of methamphetamine-like stimulants.

  DOI：

  10.1021/jm000329v
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 0.08h， 生成 2-cyano-3-(2-methoxyphenyl)acrylic acid ethyl ester
  参考文献：
  名称：

  Miyamoto, Yoshiko; Yamazaki, Chiji, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 327 - 332

  摘要：

  DOI：

文献信息

• One-by-one hydrogenation, cross-coupling reaction, and Knoevenagel condensations catalyzed by PdCl2 and the downstream palladium residue
  作者：Hu Wang、Li Li、Xing-Feng Bai、Wen-Hui Deng、Zhan-Jiang Zheng、Ke-Fang Yang、Li-Wen Xu

  DOI：10.1039/c3gc40991k

  日期：——

  A novel catalyst-economic strategy with a recovered palladium catalyst was successfully applied for multi-task and maximum reuse in different types of one-by-one downstream reactions, from catalytic hydrogenation to Suzuki and Sonogashira-type cross-coupling reactions, Knoevenagel condensations, and trans-Knoevenagel-like condensations.

  一种新型催化剂经济策略，采用回收的钯催化剂，成功应用于多种一一对应的下游反应中，实现了从催化氢化到铃木型、Sonogashira型交叉偶联反应、Knoevenagel缩合反应以及类似trans-Knoevenagel缩合反应的多任务和最大化重复利用。
• [EN] DENGUE AND WEST NILE VIRUS PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉASES DES VIRUS WEST NILE ET DE LA DENGUE
  申请人：UNIV GEORGETOWN

  公开号：WO2014164667A1

  公开（公告）日：2014-10-09

  Compounds and methods of treating or preventing a Flavivirus infection in a subject are provided. The methods comprise administering to the subject a therapeutically effective amount of a compound as described herein. The methods are useful in treating and/or preventing Flavivirus infections such as, for example, West Nile Virus, Dengue Virus, and Japanese Encephalitis Virus. Methods of inhibiting a Flavivirus protease in a cell are also provided.

  提供了一种治疗或预防受试者Flavivirus感染的化合物和方法。该方法包括向受试者施用本文所述的化合物的治疗有效量。这些方法对于治疗和/或预防Flavivirus感染非常有用，例如西尼罗河病毒、登革病毒和日本脑炎病毒。还提供了在细胞中抑制Flavivirus蛋白酶的方法。
• Simple, Efficient, and Green Method for Synthesis of Trisubstituted Electrophilic Alkenes Using Lipase as a Biocatalyst
  作者：Bhushan Nanasaheb Borse、Sanjeev Ramchandra Shukla、Yogesh Ashok Sonawane

  DOI：10.1080/00397911.2010.525334

  日期：2012.2.1

  Abstract A simple and efficient Knoevenagel condensation method for the synthesis of trisubstituted electrophilic alkenes was developed using lipase as a biocatalyst. Knoevenagel condensation was performed using the conventional method and using lipases (Aspergillus oryzae or Rhizopus oryzae) as biocatalysts, and reaction time, reaction temperature, yield, and recyclability were compared. Using a lipase

  摘要 以脂肪酶为生物催化剂，开发了一种简单高效的Knoevenagel缩合方法，用于合成三取代亲电烯烃。Knoevenagel缩合采用常规方法，以脂肪酶（米曲霉或米根霉）为生物催化剂，比较反应时间、反应温度、收率和可回收性。使用脂肪酶作为生物催化剂消除了对哌啶和吡啶等碱的需求。多种芳香醛和酮容易与活性亚甲基化合物缩合。后处理程序也非常简单，反应产率在75%到95%之间。两种生物催化剂都有效地循环了四次，产品的产率没有显着降低。脂肪酶显着的催化活性和可重复使用性扩大了其在 Knoevenagel 缩合中的适用性，在合成三取代的亲电烯烃时具有良好的收率。图形概要
• Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; unexpected reductions and vinylogations
  作者：Attimogae Shivamurthy Harisha、Suresh Parameshwar Nayak、Kuppuswamy Nagarajan、Tayur Narasingarow Guru Row、Amar A. Hosamani

  DOI：10.1016/j.tet.2016.03.097

  日期：2016.6

  Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined

  在热乙醇中将2-氰基-3-（2-甲氧基-5-硝基苯基）丙烯酸乙酯1f暴露于三乙胺导致高产率地形成二氢衍生物2f和乙烯基化合物3f。提供了用于3f的单晶X射线数据。对于各种类似物观察到相似的反应。研究了改变芳基取代基，胺和溶剂的反应。还检查了吡啶基，噻吩基类似物。该研究扩展到包含这种系统，如噻唑烷二酮的环状分子8，3-氰基香豆素9和4-亚芳基-异喹啉-2,4-二酮11。最后一组给出了乙烯基化产物，4-肉桂基-异喹啉二酮和4-羟基化的物质。研究了来自丙二腈，乙酰乙酸乙酯，乙酰丙酮和甲基磺酰乙酸乙酯的亚芳基衍生物的一些实例。肉桂酸乙酯和β-硝基苯乙烯不受影响。由于添加自由基淬灭剂抑制了反应，因此认为该反应可能是自由基介导的。与热条件的影响相反，在254和365 nm的乙醇中1f的辐照产生复杂的混合物。在这项研究中还注意到了一些其他有趣的观察结果：1f与乙醛的乙烯基化反应生成3f；从1f形成3f用
• Room Temperature, Reductive Alkylation of Activated Methylene Compounds: Carbon–Carbon Bond Formation Driven by the Rhodium-Catalyzed Water–Gas Shift Reaction
  作者：Scott E. Denmark、Malek Y. S. Ibrahim、Andrea Ambrosi

  DOI：10.1021/acscatal.6b03183

  日期：2017.1.6

  The rhodium-catalyzed water–gas shift reaction has been demonstrated to drive the reductive alkylation of several classes of activated methylene compounds at room temperature. Under catalysis by rhodium trichloride (2–3 mol %), carbon monoxide (10 bar), water (2–50 equiv), and triethylamine (2.5–7 equiv), the scope has been successfully expanded to cover a wide range of alkylating agents, including

  铑催化的水煤气变换反应已被证明可在室温下驱动几类活化的亚甲基化合物的还原烷基化反应。在三氯化铑（2-3％摩尔），一氧化碳（10 bar），水（2-50当量）和三乙胺（2.5-7当量）的催化下，其范围已成功扩大，涵盖了广泛的烷基化反应中等至高产率的包括脂肪族和芳香族醛以及环状酮在内的助剂。在某些方面，该方法与现有的还原烷基化方案相当，并且在某些方面超过了该方法。