2-formylphenyl (2E)-but-2-enoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-formylphenyl (2E)-but-2-enoate
• 英文别名: (E)-2-formylphenyl but-2-enoate；Crotonic acid, o-formylphenyl ester；(2-formylphenyl) (E)-but-2-enoate
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: MOUQACBLSHRVJO-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯胺 、 2-formylphenyl (2E)-but-2-enoate 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  分子内的1，3-偶极环加成反应由丙二胺和二氟卡宾制得的甲氧亚甲基酯的羰基

  摘要：

  Azomethinylides generated by reaction of difluorocarbene with N-alkyl- and N-arylimines of O-acylated salycilaldehyde undergo intramolecular 1,3-dipolar cycloaddition to the ester carbonyl group forming regioselectively 2,5-epoxy-1,4-benzoxazepine derivatives.

  DOI：

  10.1023/b:rujo.0000034942.42778.e0
• 作为产物：
  描述：

  乙烯基乙酸 、 水杨醛 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以42%的产率得到2-formylphenyl (2E)-but-2-enoate
  参考文献：
  名称：

  Convenient Synthesis of 3-Vinyl and 3-Styryl Coumarins

  摘要：

  A variety of 2-hydroxy aldehydes on reaction with 3-butenoic acid afford in a one-pot reaction the corresponding 3-vinylcoumarins. As expected, extension of the delocalized pi-electron system accomplished by Heck coupling reactions with aryl halides results in an increased fluorescence of the compounds whose applicability is yet to be established.

  DOI：

  10.1021/ol201983u

文献信息

• A new domino Knoevenagel-hetero-Diels–Alder reaction: an efficient catalyst-free synthesis of novel thiochromone-annulated thiopyranocoumarin derivatives in aqueous medium
  作者：Firouz Matloubi Moghaddam、Mostafa Kiamehr、Mohammad Reza Khodabakhshi、Zohreh Mirjafary、Shaghayegh Fathi、Hamdollah Saeidian

  DOI：10.1016/j.tet.2010.09.048

  日期：2010.11

  An efficient catalyst-free synthesis of novel pentacyclic thiochromone-annulated thiopyranocoumarin derivatives is achieved via domino Knoevenagel-hetero-Diels–Alder reaction of 4-hydroxy dithiocoumarin and O-acrylated salicylaldehyde derivatives in H2O as solvent. The products are formed in good yields with high regio- and stereo-selectivity.

  通过在H 2 O中以4-羟基二硫代香豆素和O-丙烯酸化的水杨醛衍生物的多米诺骨牌Knoevenagel-杂-Diels-Alder反应，可以有效地无催化剂合成新型的五环噻吩并二甲基苯并吡喃并香豆素衍生物。产物以高产率和高区域选择性和立体选择性形成。
• Discovery of Biologically Optimized Polymyxin Derivatives Facilitated by Peptide Scanning and <i>In Situ</i> Screening Chemistry
  作者：Rintaro Kaguchi、Akira Katsuyama、Toyotaka Sato、Satoshi Takahashi、Motohiro Horiuchi、Shin-ichi Yokota、Satoshi Ichikawa

  DOI：10.1021/jacs.2c12971

  日期：2023.2.15

  Peptides can be converted to highly active compounds by introducing appropriate substituents on the suitable amino acid residue. Although modifiable residues in peptides can be systematically identified by peptide scanning methodologies, there is no practical method for optimization at the “scanned” position. With the purpose of using derivatives not only for scanning but also as a starting point for

  通过在合适的氨基酸残基上引入合适的取代基，可以将肽转化为高活性化合物。虽然可以通过肽扫描方法系统地识别肽中的可修饰残基，但在“扫描”位置没有优化的实用方法。为了使用衍生物不仅用于扫描，而且作为进一步化学功能化的起点，我们在此报告了“扫描和直接衍生化”策略，通过丝氨酸/苏氨酸连接（STL）与现场帮助筛选化学。我们已将该策略应用于多粘菌素抗生素的优化，选择多粘菌素抗生素作为模型系统以突出活性扫描衍生物快速衍生化的能力。使用这种方法，我们探索了多粘菌素的构效关系，并成功制备了对多粘菌素耐药细菌和具有铜绿假单胞菌选择性抗菌活性的衍生物。该策略开辟了有效的结构探索和肽序列的进一步优化。
• Intramolecular 1,3-Dipolar Cycloaddition to Ester Carbonyl of Azomethinylides Prepared from Aldimines and Difluorocarbene
  作者：I. V. Voznyi、M. S. Novikov、A. F. Khlebnikov、J. Kopf、R. R. Kostikov

  DOI：10.1023/b:rujo.0000034942.42778.e0

  日期：2004.2

  Azomethinylides generated by reaction of difluorocarbene with N-alkyl- and N-arylimines of O-acylated salycilaldehyde undergo intramolecular 1,3-dipolar cycloaddition to the ester carbonyl group forming regioselectively 2,5-epoxy-1,4-benzoxazepine derivatives.
• Convenient Synthesis of 3-Vinyl and 3-Styryl Coumarins
  作者：Joana Gordo、João Avó、A. Jorge Parola、João C. Lima、António Pereira、Paula S. Branco

  DOI：10.1021/ol201983u

  日期：2011.10.7

  A variety of 2-hydroxy aldehydes on reaction with 3-butenoic acid afford in a one-pot reaction the corresponding 3-vinylcoumarins. As expected, extension of the delocalized pi-electron system accomplished by Heck coupling reactions with aryl halides results in an increased fluorescence of the compounds whose applicability is yet to be established.