(Z)-4-(benzylsulfanylmethylene)-2-phenyl-5(4H)-oxazolone | 121242-80-6

• 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: (Z)-4-(benzylsulfanylmethylene)-2-phenyl-5(4H)-oxazolone
• 英文别名: 4-((Z)-benzylsulfanyl-methylene)-2-phenyl-4H-oxazol-5-one；4-((Z)-Benzylmercapto-methylen)-2-phenyl-4H-oxazol-5-on；(4Z)-4-(benzylsulfanylmethylidene)-2-phenyl-1,3-oxazol-5-one
• CAS: 121242-80-6
• 化学式: C₁₇H₁₃NO₂S
• 分子量: 295.362
• InChiKey: VNNBOBGFTGUJST-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-4-(benzylsulfanylmethylene)-2-phenyl-5(4H)-oxazolone 、 环戊二烯 反应 24.0h， 生成 C₂₂H₁₉NO₂S
  参考文献：
  名称：

  Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues

  摘要：

  A new class of masked constrained cysteine derivatives containing the norbornen/ane scaffold were prepared by the way of Diets-Alder cycloaddition reaction by exploitation of two different dienophiles, sulfanyl-methylene-5(4H)-oxazolones and beta-sulfanyl-alpha-nitroacrylates. The new norbornen/ane amino acid derivatives can be considered versatile building blocks due to the presence of the alpha,alpha-disubstituted amino acid function, suitable for peptide synthesis, but also by the carbon-carbon norbornene double bond, which could be variously functionalized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.052
• 作为产物：
  描述：

  (Z)-4-(ethoxymethylene)-2-phenyloxazol-5(4H)-one 生成 (Z)-4-(benzylsulfanylmethylene)-2-phenyl-5(4H)-oxazolone
  参考文献：
  名称：

  Mukerjee Arya K., Rao Laxmi, Homami Seyed Saied, Joseph Kiran, Can. J. Chem, 72 (1994) N 5, S 1383-1387

  摘要：

  DOI：

文献信息

• Umsetzungen von 4-Aminomethylen-5-oxo-2-phenyl-4,5-dihydrooxazol mit Heterocumulenen
  作者：I. Thondorf、M. Strube、M. Augustin

  DOI：10.1055/s-1990-27126

  日期：——

  Reactions of 4-Aminomethylene-5-oxo-2-phenyl-4,5-dihydrooxazole with Heterocumulenes The reaction of 4-aminomethylene-5-oxo-2-phenyl-4,5-dihydro-oxazole (1) with various heterocumulenes under basic conditions was examined. Depending on the nature of the heterocumulene different products were obtained. The reaction of 1 with carbon disulfide followed by alkylation yielded only 4-alkylthiomethylene-2-phenyl-5-oxo-4,5-dihydrooxazoles whereas the reaction of 1 with isothiocyanates, isocyanates and carbonyl sulfide led to the formation of 5-benzoylamino-2-thiouracils, 5-benzoylaminouracils and of 5-benzoylamino-2-methylthio-6H-1,3-oxazin-6-one, respectively.

  4-氨基亚甲基-5-氧-2-苯基-4,5-二氢恶唑与杂累积双键的反应 在碱性条件下，研究了4-氨基亚甲基-5-氧-2-苯基-4,5-二氢恶唑（1）与各种杂累积双键的反应。根据杂累积双键的性质，得到了不同的产物。1与二硫化碳反应后进行烷基化，只产生4-烷硫基亚甲基-2-苯基-5-氧-4,5-二氢恶唑；而1与异硫氰酸酯、异氰酸酯和碳酰硫反应，则分别形成5-苯甲酰氨基-2-硫尿嘧啶、5-苯甲酰氨基尿嘧啶和5-苯甲酰氨基-2-甲硫基-6H-1,3-恶嗪-6-酮。
• A Novel Class of Conformationally Constrained, Masked Cysteines:  Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids
  作者：F. Clerici、M. L. Gelmi、D. Pocar

  DOI：10.1021/jo9810011

  日期：1999.2.1

  4-(chloromethylene)oxazolone 1 and mercaptans 2. Oxazolones 3 were used as starting materials for the preparation of unknown 2-sulfanyl-1-aminocyclopropanecarboxylic acid derivatives 5 and7. Oxazolones 3 were cyclopropanated at the exocyclic double bond with diazomethane, giving a mixture of the two (Z)- and (E)-spirocyclopropane oxazolones 4 with good diastereoselectivity. These were then treated with

  从4-（氯亚甲基）恶唑酮1和硫醇2开始实现了4-硫烷基亚甲基-5（4H）-恶唑酮3的方便合成。恶唑酮3被用作制备未知的2-硫烷基-1-氨基环丙烷羧酸的起始原料导数5和7。恶唑酮3在环外双键处与重氮甲烷环丙烷化，得到具有良好非对映选择性的两种（Z）-和（E）-螺环丙烷恶唑酮4的混合物。然后将它们用乙醇和DMAP处理以产生相应的羧酸盐5。使用碘在乙醇溶液中的溶液，将三苯甲基衍生物5d转化为非对映异构体二硫化物6的混合物。二硫化物6是用于制备3-硫烷基取代的2,3-甲基氨基酸7的便利合成子。
• Tsukita, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1949, vol. 69, p. 102
  作者：Tsukita

  DOI：——

  日期：——
• Cornforth, Chemistry of Penicillin
  作者：Cornforth

  DOI：——

  日期：——
• Baltrazzi; Davis, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1955, vol. 240, p. 208
  作者：Baltrazzi、Davis

  DOI：——

  日期：——