2-phenyl-4-isopropylidene-5(4H)oxazolone | 4491-47-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-phenyl-4-isopropylidene-5(4H)oxazolone
• 英文别名: 2-phenyl-4-isopropylidene-Δ²-oxazolin-5-one；2-Phenyl-4-isopropyliden-oxazolon-(5)；2-Oxazolin-5-one, 4-isopropylidene-2-phenyl-；2-phenyl-4-propan-2-ylidene-1,3-oxazol-5-one
• CAS: 4491-47-8
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD00091992
• 分子量: 201.225
• InChiKey: FSYXZIPYOMWJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-isopropylidene-5(4H)oxazolone 在 硫酸 作用下， 生成 methyl 2-benzamido-3-methylbut-2-enoate
  参考文献：
  名称：

  Cornforth, Chemistry of Penicillin

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Benzoylamino-3-methyl-butensaeureazid 在 溶剂黄146 作用下， 反应 1.0h， 生成 2-phenyl-4-isopropylidene-5(4H)oxazolone
  参考文献：
  名称：

  Studies on the Azidolysis of 4-Arylidene- and 4-Alkylidene-5-oxazolones

  摘要：

  DOI：

  10.1021/jo01018a025

文献信息

• Cycloaddition of 4,5-Dihydrooxazol-5-one Derivatives to 4-Methylbenzene-1,2-dithiol
  作者：A. M. Tikdari、S. Fozooni、H. Vazee、H. Hamidian

  DOI：10.1007/s11178-005-0291-y

  日期：2005.7

  Reactions of 4,5-dihydrooxazol-5-one derivatives with 4-methylbenzene-1,2-dithiol in the presence of triethylamine includes nucleophilic attack by the thiol group on the carbonyl carbon atom in the oxazole ring, followed by opening of the latter and recyclization to 1,4-benzodithiine derivatives.

  在三乙胺存在下，4,5-二氢噁唑-5-酮衍生物与4-甲基苯-1,2-二硫酚的反应涉及硫醇基团对噁唑环中的羰基碳原子的亲核攻击，随后噁唑环的打开并重新环合，形成1,4-苯并二硫因衍生物。
• A Simple and Convenient Synthesis of 4-Ylidene-5(4<i>H</i>)oxazolone Derivatives: Oxazolone Ring Transformation Leading to Other Heterocyclic Structures
  作者：Ramadan M. Abdel-Motaleb、Hadeer M. Bakeer、Gammal H. Tamam、Wael A. A. Arafa

  DOI：10.1002/jhet.938

  日期：2012.9

  yield synthetic procedure for the synthesis of 4‐ylidene‐5(4H)‐oxazolones 2a–m from arylidene‐malononitriles under solvent‐free conditions is described. The scope of this reaction was investigated, and it was found that the presence of anhydrous sodium acetate gave the corresponding oxazolones in excellent yields. The newly generated oxazolone derivative 2m underwent ring transformation into pyrroles,

  描述了一种简单，有效且高收率的合成方法，该方法可在无溶剂条件下从亚芳基丙二腈合成2亚胺5a -m（4 H）-恶唑酮2a-m。研究了该反应的范围，发现无水乙酸钠的存在以优异的产率得到了相应的恶唑酮。新产生的恶唑酮衍生物2m进行环转化为吡咯，咪唑，哒嗪和三嗪。
• 4-[3-Dimethylamino-1-(2-dimethylaminovinyl]prop-2-enylidene]-2-phenyl-1,3-oxazol-5(4H)-one and 5-[3-Dimethylamino-1-(2-dimethylaminovinyl)prop-2-enylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one in the Synthesis of 1,4-Dihydropyridine Derivatives
  作者：Branko Stanovnik、Ales Hvala、Lucija Jukic Sorsak、Gorazd Sorsak、Urska Bratusek、Jurij Svete、Nina Lah、Ivan Leban

  DOI：10.3987/com-02-9433

  日期：——

  afforded 1,4-dihydropyridine derivatives (5) and (16) in 19-94% yields. Reactions of oxazolones (5) with hydrazine hydrate gave the corresponding imidazolones (6), while upon base- or acid-catalysed methanolysis of 5 methyl (benzoylamino)(1-substituted pyridin-4(1H)-ylidene)acetates (7) were obtained. Catalytic hydrogenation of 7a furnished α-(piperidin-4-yl)glycine derivative (8) and/or α-(pyridin-2-yl)glycine

  4-3-二甲氨基-1-[2-(二甲氨基)乙烯基]丙-2-亚乙烯基]-2-苯基-1,3-恶唑-5(4H)-一(3)和5-3-二甲氨基-1-[2-(二甲基氨基)乙烯基]prop-2-enylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one (15) 由 4-(1-methylethyleneidene) 制备-2-phenyl-1,3-oxazol-5(4H)-one (2) 和 5-(1-methylethyleneidene)-2-thioxo-1,3-thiazolidin-4-one (11)。用伯胺处理化合物(3)和(15)得到19-94％产率的1，4-二氢吡啶衍生物(5)和(16)。恶唑酮 (5) 与水合肼反应得到相应的咪唑酮 (6)，而在碱或酸催化的 5 甲基 (苯甲酰氨基)(1-取代的吡啶-4(1H)-亚甲基)乙酸酯 (7) 的甲醇分解下，获得。7a
• Synthesis, Anticholinesterase, and Antibacterial Activity of N-Aroyl-a-Aminoacrylic Acid Dialkylaminoalkylamides
  作者：V. O. Topuzyan、Z. G. Alebyan、R. V. Paronikyan

  DOI：10.1007/s11094-015-1274-0

  日期：2015.8

  N-Aroyl-α-aminoacrylic acid 2-(dialkylamino)alkylamides and their quaternary ammonium salts were synthesized and their physicochemical properties were determined. Results obtained from studies of their interactions with human erythrocyte acetylcholinesterase (AChE) and plasma butyrylcholinesterase (BChE) are presented. IC50 values (concentrations producing 50% inhibition of the rate of cholinesterase hydrolysis of 0.1 mM acetylthiocholine) were determined for all the compounds synthesized. The results show that all the compounds synthesized had anticholinesterase properties, mainly specific in relation to BChE. Data on the antibacterial properties of the synthesized compounds are also presented.

  合成了N-芳酰-α-氨基丙烯酸2-(二烷基氨基)烷基酰胺及其季铵盐，并确定了它们的物理化学性质。本文呈现了它们与人类红细胞乙酰胆碱酯酶（AChE）和血浆丁酰胆碱酯酶（BChE）相互作用的研究结果。为所有合成的化合物确定了IC50值（产生50%抑制0.1 mM乙酰硫胆碱水解速率的浓度）。结果表明，所有合成的化合物具备抗胆碱酯酶特性，主要是相对于BChE。文中还呈现了合成化合物的抗菌特性数据。
• Cyclopropane analogue of valine: influence of side chain orientation on peptide folding
  作者：Ana I. Jiménez、Michel Marraud、Carlos Cativiela

  DOI：10.1016/s0040-4039(03)00514-8

  日期：2003.4

  The cyclopropane analogue of valine (1-amino-2,2-dimethylcyclopropanecarboxylic acid, c3Val) has been synthesised and incorporated into the model peptides tBuCO-l-Pro-l-c3Val-NHiPr and tBuCO-l-Pro-d-c3Val-NHiPr. In the solid state, both dipeptides accommodate a type II β-turn stabilised by an NHiPr to tBuCO hydrogen bond. Remarkably, the peptide incorporating l-c3Val also exhibits a distorted γ-turn

  已合成缬氨酸的环丙烷类似物（1-氨基-2,2-二甲基环丙烷羧酸，c 3 Val）并将其掺入模型肽t BuCO-1-Pro-lc 3 Val-NH i Pr和t BuCO-1- Pro-dc 3 Val-NH i Pr。在固态下，两个二肽都具有通过NH i Pr到t BuCO氢键稳定的II型β-转角。引人注目的是，掺有lc 3 Val的肽在环丙烷残基周围也表现出扭曲的γ转角，Pro-CO和NH i Pr分子内氢键。