3-(3,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester | 5864-90-4

• 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: 3-(3,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester
• 英文别名: ethyl 3-(3,5-dimethoxyphenyl)-2-cyanoacrylate；ethyl 2-cyano-3-(3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 5864-90-4
• 化学式: C₁₄H₁₅NO₄
• mdl: MFCD00176591
• 分子量: 261.277
• InChiKey: XQYIEYWLUZICRD-UHFFFAOYSA-N

物化性质

• 沸点：
  416.6±45.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester 、 N-溴代乙酰胺 在 potassium phosphate 作用下， 以 丙酮 为溶剂， 反应 4.5h， 以85%的产率得到5-cyano-5-ethoxyformacyl-4-(3,5-dimethoxyphenyl)-2-methyl-4,5-dihydrooxazole
  参考文献：
  名称：

  One-Pot Synthesis of 2-Oxazolines from Ethylα-Cyanocinnamate Derivatives withN-Bromoacetamide

  摘要：

  An efficient method for the one‐pot synthesis of 2‐oxazolines from ethyl α‐cyanocinnamate derivatives with N‐bromoacetamide in the presence of K3PO4 has been developed. The reaction performed smoothly and cleanly to give 2‐oxazolines in good to excellent yields (up to 98%) within 4.5 h in acetone at room temperature without protection of inert gases. A total of 13 examples have been investigated. A possible nucleophilic addition reaction mechanism is proposed.

  DOI：

  10.1002/jhet.1902
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 氰乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以90%的产率得到3-(3,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester
  参考文献：
  名称：

  使用氰乙酸乙酯通过氮杂-迈克尔-迈克尔加成合成高度取代的四氢喹啉

  摘要：

  据报道，在 DBU 存在下，涉及 2-烯基苯胺、醛和氰基乙酸乙酯的三组分级联反应合成了高度取代的 1,2,3,4-四氢喹啉。该反应通过氰基乙酸乙酯与醛的 Knoevenagel 缩合进行，然后与 2-烯基苯胺进行氮杂-迈克尔-迈克尔加成，制备四氢喹啉支架。

  DOI：

  10.1039/d0ra01264e

文献信息

• Substituted coumarins and quinolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20050090526A1

  公开（公告）日：2005-04-28

  The present invention is directed to substituted coumarins and quinolines and analogs thereof, represented by the general Formula I: wherein A, B, X, Y, and Z are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及替代香豆素和喹啉及其类似物，其由通式I所表示：其中，A、B、X、Y和Z在此定义。本发明还涉及发现具有I式化合物是caspase激活剂和诱导细胞凋亡剂。因此，本发明的caspase激活剂和诱导细胞凋亡剂可用于诱导在各种临床情况下出现的不受控制的异常细胞的生长和扩散的细胞死亡。
• The preparation and reaction of enolates within micro reactors
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell、Esteban Pombo-Villar

  DOI：10.1016/j.tet.2005.08.076

  日期：2005.11

  Over the past 5 years, interest in the miniaturisation of chemical synthesis has grown rapidly, however in order to facilitate transfer of the technology from its current position as a research tool to industrial applications, a core understanding of the challenges associated with transferring reactions from the macro to the micro domain is required. This paper therefore aims to broach this problem by investigating the application of micro reactors to a range of commonly employed synthetic reactions including acylation, aldol, alkylation, 1,4-conjugate addition (Michael addition) and the Knoevenagel condensation. Comparison of the results obtained with traditional batch techniques enable us to highlight some of the advantages associated with micro reaction technology. (c) 2005 Elsevier Ltd. All rights reserved.
• Discovery of 4-aryl-2-oxo-2H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay
  作者：William Kemnitzer、Songchun Jiang、Hong Zhang、Shailaja Kasibhatla、Candace Crogan-Grundy、Charles Blais、Giorgio Attardo、Real Denis、Serge Lamothe、Henriette Gourdeau、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2008.09.011

  日期：2008.10

  As a continuation of our efforts to discover and develop the apoptosis inducing 4-aryl-4H-chromenes as potential anticancer agents, we explored the removal of the chiral center at the 4-position and prepared a series of 4-aryl-2-oxo-2H-chromenes. It was found that, in general, removal of the chiral center and replacement of the 2-amino group with a 2-oxo group were tolerated and 4-aryl-2-oxo-2H-chromenes exhibited SAR similar to 4-aryl-2-amino-4H-chromenes. The 4-aryl-2-oxo-2H-chromenes with a N-methyl pyrrole fused at the 7,8-positions were highly active with compound 2a having an EC(50) value of 13 nM in T47D cells. It was found that an OMe group was preferred at the 7-positon. 7-NMe(2), 7-NH(2), 7-Cl and 7,8 fused pyrido analogs all had low potency. These 4-aryl-2-oxo-2H-chromenes are a series of potent apoptosis inducers with potential advantage over the 4-aryl-2-amino-4H-chromenes series via elimination of the chiral center at the 4-position. (C) 2008 Elsevier Ltd. All rights reserved.
• Three-component synthesis of some 2-amino-5-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles and 2-(cyanoamino)-4-hydroxypyrimidine-5-carbonitriles
  作者：Reza Ranjbar-Karimi、Khalil Beiki-Shoraki、Asghar Amiri

  DOI：10.1007/s00706-010-0371-8

  日期：2010.10

  Nine new 2-amino-5-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles and eight 2-(cyanoamino)-4-hydroxypyrimidine-5-carbonitriles have been synthesized in a simple and convenient method by three-component condensation of aromatic aldehydes, ethyl cyanoacetate, and 3,5-diamino-1,2,4-triazole or cyanoguanidine hydrochloride in alkaline ethanol. All new synthesized compounds were characterized by nuclear magnetic resonance (NMR), infrared (IR), ultraviolet (UV), mass spectrometry (MS), and elemental analyses.
• Solid-Supported Continuous Flow Synthesis in Microreactors Using Electroosmotic Flow
  作者：Nikzad Nikbin、Paul Watts

  DOI：10.1021/op049857x

  日期：2004.11.1

  This paper reports the fabrication of a microreactor suitable for use with supported reagents. We demonstrate that the electroosmotic flow can be used to move the reagents over a solid-supported catalyst bed. It is demonstrated that it is important that the support should not swell in organic solvents to obtain reproducible flow, and it is shown that silica supports fulfill this criteria. Silica-functionalised piperazine is used in a variety of Knoevenagel reactions to give the product in high conversion.