Ethyl 3-(4-hydroxyphenyl)-2-methylprop-2-enoate | 50906-06-4

• 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: Ethyl 3-(4-hydroxyphenyl)-2-methylprop-2-enoate
• CAS: 50906-06-4
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: ZIWCQHXHXZTNTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(4-hydroxyphenyl)-2-methylprop-2-enoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3-(4-hydroxyphenyl)-2-methylacrylic acid
  参考文献：
  名称：

  Analogue Chromophore Study of the Influence of Electronic Perturbation on Color Regulation of Photoactive Yellow Protein†

  摘要：

  We report a unique lambda(max) shift of the absorption maximum of a photoactive yellow protein (PYP) analogue reconstituted with a fluorinated chromophore (F-PYP). The difference in lambda(max), between the free chromophore and the protein was significantly larger than that with the native chromophore. We concluded that the unusual,lambda(max) shift is caused by the electronegative character of the fluorine atom and not by steric hindrance. This result suggests that formation of a hydrogen bond between the fluorine atom and one or more amino acid residues could neutralize its electron-withdrawing character. The properties of analogues of PYP with brominated and methylated chromophore could be explained as an effect of steric hindrance.

  DOI：

  10.1562/2006-01-17-ra-781
• 作为产物：
  描述：

  4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 5.0h， 生成 Ethyl 3-(4-hydroxyphenyl)-2-methylprop-2-enoate
  参考文献：
  名称：

  Analogue Chromophore Study of the Influence of Electronic Perturbation on Color Regulation of Photoactive Yellow Protein†

  摘要：

  We report a unique lambda(max) shift of the absorption maximum of a photoactive yellow protein (PYP) analogue reconstituted with a fluorinated chromophore (F-PYP). The difference in lambda(max), between the free chromophore and the protein was significantly larger than that with the native chromophore. We concluded that the unusual,lambda(max) shift is caused by the electronegative character of the fluorine atom and not by steric hindrance. This result suggests that formation of a hydrogen bond between the fluorine atom and one or more amino acid residues could neutralize its electron-withdrawing character. The properties of analogues of PYP with brominated and methylated chromophore could be explained as an effect of steric hindrance.

  DOI：

  10.1562/2006-01-17-ra-781

文献信息

• Stereoselective synthesis of aryl 1,2- cis -furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A
  作者：Yuan Xu、Hua-Chao Bin、Fu Su、Jin-Song Yang

  DOI：10.1016/j.tetlet.2017.02.079

  日期：2017.4

  An efficient methodology for the synthesis of aryl 1,2-cis-furanosidic linkages has been developed with 2-quinolinecarbonyl (Quin) group substituted furanose ethyl thioglycosides as glycosyl donors. The method permits a wide range of phenol acceptors to be used, thus resulting in the formation of structurally diverse phenol furanosides in good to excellent chemical yields with complete 1,2-cis anomeric

  用2-喹啉基羰基（Quin）基团取代的呋喃糖乙基硫代糖苷作为糖基供体，已经开发了一种有效的合成芳基1，2-顺式-呋喃基键的方法。该方法允许使用广泛的苯酚受体，因此导致形成结构多样的苯酚呋喃糖苷，具有良好的化学产率和完全的1,2-顺式异头异构体选择性。该方法的合成效用已通过简明制备抗生素潮霉素A的碳水化合物部分得到了证明。
• Analogue Chromophore Study of the Influence of Electronic Perturbation on Color Regulation of Photoactive Yellow Protein†
  作者：Hiroshi Yamada、Masato Kumauchi、Norio Hamada、Xiang-Guo Zheng、Il Ho Park、Katsuyoshi Masuda、Kazuo Yoshihara、Fumio Tokunaga

  DOI：10.1562/2006-01-17-ra-781

  日期：——

  We report a unique lambda(max) shift of the absorption maximum of a photoactive yellow protein (PYP) analogue reconstituted with a fluorinated chromophore (F-PYP). The difference in lambda(max), between the free chromophore and the protein was significantly larger than that with the native chromophore. We concluded that the unusual,lambda(max) shift is caused by the electronegative character of the fluorine atom and not by steric hindrance. This result suggests that formation of a hydrogen bond between the fluorine atom and one or more amino acid residues could neutralize its electron-withdrawing character. The properties of analogues of PYP with brominated and methylated chromophore could be explained as an effect of steric hindrance.