(E)-4-(furan-2-yl)-4-oxobut-2-enoic acid | 117379-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-(furan-2-yl)-4-oxobut-2-enoic acid
• CAS: 117379-47-2
• 化学式: C₈H₆O₄
• 分子量: 166.133
• InChiKey: QVKNVTSRNCZBKB-ONEGZZNKSA-N

物化性质

• 熔点：
  153-155 °C(Solv: isopropanol (67-63-0))
• 沸点：
  315.4±38.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-(furan-2-yl)-4-oxobut-2-enoic acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.17h， 生成 (2S,4R,1'S)-4-(furan-2-yl)-4-hydroxy-2-[(1'-phenylethyl)amino]-butanoic acid
  参考文献：
  名称：

  Crystallisation induced asymmetric transformation (CIAT) in the synthesis of furoylalanines and furylcarbinols

  摘要：

  A new synthesis of enantiomerically highly enriched N-substituted furoylalanines has been developed. This process involves the combination of crystallisation induced asymmetric transformation (CIAT) and a conjugate addition of N-nucleophiles to furoylacrylic acids. Further transformations to furoylalanines and substituted furylcarbinols are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.024
• 作为产物：
  描述：

  4-(2-furyl)-2-hydroxy-4-oxobutanoic acid 在 potassium hydrogensulfate 作用下， 以 水 、 甲苯 为溶剂， 反应 2.5h， 以11.891 g的产率得到(E)-4-(furan-2-yl)-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Crystallisation induced asymmetric transformation (CIAT) in the synthesis of furoylalanines and furylcarbinols

  摘要：

  A new synthesis of enantiomerically highly enriched N-substituted furoylalanines has been developed. This process involves the combination of crystallisation induced asymmetric transformation (CIAT) and a conjugate addition of N-nucleophiles to furoylacrylic acids. Further transformations to furoylalanines and substituted furylcarbinols are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.024

文献信息

• Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
  作者：Changliang Xu、Xiaoguang Bai、Jian Xu、Jinfeng Ren、Yun Xing、Ziqiang Li、Juxian Wang、Jingjing Shi、Liyan Yu、Yucheng Wang

  DOI：10.1039/c6ra24953a

  日期：——

  Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the

  蛋白激酶B（PknB）是结核分枝杆菌（M. tb）细胞分裂和细胞壁生物合成所必需的丝氨酸/苏氨酸蛋白激酶。使用PknB进行的高通量筛选鉴定出一种名为YH-8的（E）-4-氧代巴豆酸抑制剂，该抑制剂被用作SAR研究的支架。实现了酶亲和力的显着改善。结果表明，α，β-不饱和酮骨架和“反式”构型对于对抗PknB的活性至关重要。而且具有芳基的化合物，特别是在苯环上具有吸电子取代基的化合物，其效能是YH-8的四倍。
• Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
  作者：Jinfeng Ren、Jian Xu、Guoning Zhang、Changliang Xu、LiLi Zhao、XueFu You、Yucheng Wang、Yu Lu、Liyan Yu、Juxian Wang

  DOI：10.1016/j.bmcl.2019.01.001

  日期：2019.2

  A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against

  设计并合成了一系列新颖的（E）-4-氧代-2-巴豆酰胺衍生物，以寻找有效的抗结核药。评价所有目标化合物的抗结核分枝杆菌H37Rv（MTB）的体外活性。结果表明，发现A部分的4-苯基部分和C部分的短甲基是有利的。大多数衍生物显示出对MTB有希望的活性，MIC为0.125至4 µg / mL。尤其是，发现化合物IIIa16对MTB的MIC最佳活性为0.125μg/ mL，对耐药性临床MTB分离株的MIC最佳为0.05-0.48μg/ mL。
• Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives
  作者：Shanxue Yang、Lan Yao、Zhenhua Fan、Jing Han、Jie Chen、Weimin He、Hongmei Deng、Min Shao、Hui Zhang、Weiguo Cao

  DOI：10.1016/j.jfluchem.2021.109723

  日期：2021.3

  The highly diastereoselective synthesis of perfluoroalkyl-containing pyrano[3,4-c]pyrroles has been accomplished via a cascade process involving Michael addition, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction. This domino transformation of isocyanides, methyl perfluoroalk-2-ynoates and 3-aroyl (or heteroyl) acrylic acids proceeded smoothly at room temperature and led to

  含全氟烷基的吡喃并[3,4- c ]吡咯的高度非对映选择性合成是通过级联过程完成的，该过程涉及迈克尔加成，Passerini型反应，Mumm重排和羰基-狄尔斯-阿尔德反应。异氰酸酯，全氟烷-2-甲基丙烯酸甲酯和3-芳酰基（或杂芳基）丙烯酸的多米诺骨转化在室温下平稳进行，并导致形成具有高官能团相容性的高非对映选择性目标化合物，并具有良好的产率。
• A simple, diversity oriented synthesis of highly substituted pyridines
  作者：Katarzyna Kaczanowska、Holger Eickhoff、Klaus Albert、Karl-Heinz Wiesmüller、Arnaud-Pierre Schaffner

  DOI：10.1002/jhet.614

  日期：2011.7

  A particularly straightforward and efficient protocol for the synthesis of highly substituted pyridines, based on a condensation reaction of β‐aminocrotonitrile and easily accessible (E)‐2‐oxo‐4‐aryl‐but‐3‐enoic acids and (E)‐4‐oxo‐4‐aryl‐but‐2‐enoic acids is described. J. Heterocyclic Chem., (2011).

  基于β-氨基丁腈和容易获得的（E）-2-氧代-4-芳基-丁-3-丁烯酸和（E）-4的缩合反应，用于合成高度取代的吡啶的特别简单有效的方法描述了-氧--4-芳基-丁-2-烯酸。J.杂环化​​学。（2011）。
• Mercaptoacyldihydropyrazole carboxylic acid derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04254267A1

  公开（公告）日：1981-03-03

  Hypotensive activity is exhibited by compounds having the formula ##STR1## wherein: R.sub.1 is hydrogen, alkyl, aryl, arylalkyl or ##STR2## wherein R.sub.5 is alkyl or aryl; R.sub.2 is hydrogen, alkyl, or haloalkyl; R.sub.3 is furanyl, thienyl or pyridyl; R.sub.4 is hydrogen, alkyl or arylalkyl; and n is 0, 1 or 2.

  具有以下公式##STR1##的化合物表现出降压活性：其中：R.sub.1是氢、烷基、芳基、芳基烷基或##STR2##其中R.sub.5是烷基或芳基；R.sub.2是氢、烷基或卤代烷基；R.sub.3是呋喃基、噻吩基或吡啶基；R.sub.4是氢、烷基或芳基烷基；n为0、1或2。