4-fluorobenzalcyanoacetic acid | 118409-66-8

• 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: 4-fluorobenzalcyanoacetic acid
• 英文别名: 2-cyano-3-(4-fluorophenyl)acrylic acid；2-cyano-3-(4-fluorophenyl)-2-propenoic acid；2-Cyano-3-(4-fluorophenyl)prop-2-enoic acid
• CAS: 118409-66-8
• 化学式: C₁₀H₆FNO₂
• mdl: MFCD04612001
• 分子量: 191.162
• InChiKey: OBZAFMILNGLRAL-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于甲醇：溶解度为100mg/10mL，澄清，无色至淡黄色

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-fluorobenzalcyanoacetic acid 、 双氢青蒿素 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以51%的产率得到
  参考文献：
  名称：

  Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104903
• 作为产物：
  描述：

  α-氰基-4-氟肉桂酸乙酯 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以63%的产率得到4-fluorobenzalcyanoacetic acid
  参考文献：
  名称：

  Mishriky; Girgis; Ahmed-Farag, Egyptian Journal of Chemistry, 2009, vol. 52, # 2, p. 249 - 264

  摘要：

  DOI：

文献信息

• One-Pot Esterification and Amide Formation via Acid-Catalyzed Dehydration and Ritter Reactions
  作者：Pankaj Dawar、M. Bagavan Raju、Ramesha Andagar Ramakrishna

  DOI：10.1080/00397911.2013.837485

  日期：2014.3.19

  Esterification of carboxylic acid is achieved using acetonitrile as a water trap. Water liberated during esterification is consumed in cyanide hydrolysis, thereby driving the esterification to completion. Substrates having carboxylic acid and nitrile groups undergo intramolecular dehydration and rehydration to amido esters in the absence of acetonitrile. Cyano acids also undergo esterification and Ritter reaction in one pot when excess alcohol is used. For the first time, we have observed an interesting Ritter reaction of primary alcohols, leading to ester amide product in one pot. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Sandhar, Randeep Kaur; Sharma; Manrao, Journal of the Indian Chemical Society, 2006, vol. 83, # 3, p. 263 - 265
  作者：Sandhar, Randeep Kaur、Sharma、Manrao

  DOI：——

  日期：——
• Monocarboxylate Transporter 1 Inhibitors as Potential Anticancer Agents
  作者：Shirisha Gurrapu、Sravan K. Jonnalagadda、Mohammad A. Alam、Grady L. Nelson、Mary G. Sneve、Lester R. Drewes、Venkatram R. Mereddy

  DOI：10.1021/acsmedchemlett.5b00049

  日期：2015.5.14

  Potent monocarboxylate transporter I inhibitors (MCTI) have been developed based on alpha-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCTI inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.
• Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway
  作者：Yanping Hu、Yujin Wang、Na Li、Li Chen、Jianbo Sun

  DOI：10.1016/j.bioorg.2021.104903

  日期：2021.6
• Mishriky; Girgis; Ahmed-Farag, Egyptian Journal of Chemistry, 2009, vol. 52, # 2, p. 249 - 264
  作者：Mishriky、Girgis、Ahmed-Farag

  DOI：——

  日期：——