3-[5-(4-溴苯基)呋喃-2-基]丙-2-烯酸 | 62806-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[5-(4-溴苯基)呋喃-2-基]丙-2-烯酸
• 英文名称: (E)-3-(5-(4-bromophenyl)furan-2-yl)acrylic acid
• 英文别名: (2E)-3-[5-(4-bromophenyl)furan-2-yl]prop-2-enoic acid；(E)-3-[5-(4-bromophenyl)furan-2-yl]prop-2-enoic acid
• CAS: 62806-35-3
• 化学式: C₁₃H₉BrO₃
• mdl: MFCD00445746
• 分子量: 293.117
• InChiKey: UWJPYZVCZQFJDI-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[5-(4-溴苯基)呋喃-2-基]丙-2-烯酸 在 二氧化碳 、 phenylalanine ammonia-lyase 、 氨 作用下， 以 水 为溶剂， 反应 96.0h， 以89%的产率得到2-amino-3-[5-(4-bromophenyl)furan-2-yl]propanoic acid
  参考文献：
  名称：

  2-Amino-3-(5-phenylfuran-2-yl)propionic Acids and 5-Phenylfuran-2-ylacrylic Acids are Novel Substrates of Phenylalanine Ammonia-Lyase

  摘要：

  Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, H-1-NMR and C-13-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-1a) para-Br (rac-1b) or Cl para or ortho (rac-1c, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10.

  DOI：

  10.3987/com-10-s(e)60
• 作为产物：
  描述：

  [5-(4-溴苯基)-2-呋喃]甲醇 在 盐酸 、 氯化亚砜 、 phenylalanine ammonia-lyase 、 水 、 sodium hydride 、 1-羟基苯并三唑 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 218.5h， 生成 3-[5-(4-溴苯基)呋喃-2-基]丙-2-烯酸
  参考文献：
  名称：

  2-Amino-3-(5-phenylfuran-2-yl)propionic Acids and 5-Phenylfuran-2-ylacrylic Acids are Novel Substrates of Phenylalanine Ammonia-Lyase

  摘要：

  Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, H-1-NMR and C-13-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-1a) para-Br (rac-1b) or Cl para or ortho (rac-1c, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10.

  DOI：

  10.3987/com-10-s(e)60

文献信息

• Structure–Activity relationships of novel anti-Malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides
  作者：Jochen Wiesner、Andreas Mitsch、Pia Wißner、Oliver Krämer、Hassan Jomaa、Martin Schlitzer

  DOI：10.1016/s0960-894x(02)00555-3

  日期：2002.10

  In a previous report, we have described novel anti-malarial compounds based on a 2,5-diaminobenzophenone scaffold. Here, we have invesigated acryloyl derivatives carrying a biaryl structure consisting of a terminal aryl residue and a central 2-furyl ring. Several compounds were obtained in the series of para-substituted phenylfurylacryloyl derivatives that displayed improved anti-malarial activity in comparison to earlier described derivatives. From the structure-activity relationships it can be deduced that there has to be a lipophilic moiety in the para-position of the terminal phenyl residue. Furthermore, there are indications that, alternatively, activity may benefit from the presence of a polar moiety with hydrogen bond acceptor properties. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Obushak, N. D.; Ganushchak, N. I.; Lesyuk, A. I., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 4, p. 748 - 753
  作者：Obushak, N. D.、Ganushchak, N. I.、Lesyuk, A. I.、Dzikovskaya, L. M.、Kisilitsa, P. P.

  DOI：——

  日期：——
• OBUSHAK, N. D.;GANUSHCHAK, N. I.;LESYUK, A. I.;DZIKOVSKAYA, L. M.;KISILIT+, ZH. ORGAN. XIMII, 26,(1990) N, S. 873-880
  作者：OBUSHAK, N. D.、GANUSHCHAK, N. I.、LESYUK, A. I.、DZIKOVSKAYA, L. M.、KISILIT+

  DOI：——

  日期：——
• LESYUK A. I.; DZIKOVSKAYA L. M.; OBUSHAK N. D.; GANUSHCHAK N. I., BECTH. LVOV. YH-TA. CEP. XIM.,(1987) N 28, 82-86
  作者：LESYUK A. I.、 DZIKOVSKAYA L. M.、 OBUSHAK N. D.、 GANUSHCHAK N. I.

  DOI：——

  日期：——
• 2-Amino-3-(5-phenylfuran-2-yl)propionic Acids and 5-Phenylfuran-2-ylacrylic Acids are Novel Substrates of Phenylalanine Ammonia-Lyase
  作者：János Rétey、Csaba Paizs、Monica Ioana Toşa、László Csaba Bencze、Jürgen Brem、Florin Dan Irimie

  DOI：10.3987/com-10-s(e)60

  日期：——

  Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, H-1-NMR and C-13-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-1a) para-Br (rac-1b) or Cl para or ortho (rac-1c, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10.