(E)-2-methyl-4-(naphthalen-1-ylmethylene)oxazol-5(4H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-methyl-4-(naphthalen-1-ylmethylene)oxazol-5(4H)-one
• 英文别名: (4E)-2-methyl-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5-one
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: SOZGZXBLNWADNY-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-2-methyl-4-(1-naphthylmethylene)-5(4H)-oxazolone 以 乙腈 为溶剂， 以17%的产率得到(E)-2-methyl-4-(naphthalen-1-ylmethylene)oxazol-5(4H)-one
  参考文献：
  名称：

  Benzylidene-Oxazolones as Molecular Photoswitches

  摘要：

  The synthesis and photochemical study of a family of molecular switches inspired by the green fluorescent protein (UP) chromophore is presented. These compounds can be easily synthesized, and their photophysical properties may be tuned. Due to their efficient photoisomerization and high stability, these compounds can be switched on/off by using light and heat or light with different wavelengths.

  DOI：

  10.1021/ol301741g

文献信息

• SULFUR- AND N-ACYL CARBONYL OXYGEN-ASSISTED HETEROLYSIS OF THE C(=O)–S BOND IN EXCITED-STATE (Z)-N-ACYL-α-DEHYDRO(1-NAPHTHYL)ALANINE THIOESTERS
  作者：Tadamitsu Sakurai、Yosuke Hosoi、Tetsutaro Igarashi

  DOI：10.3987/com-12-s(n)17

  日期：——

  Irradiation of the title thioesters (Z)-1 in nitrogen-saturated 1,2-dichloroethane at wavelengths greater, than 280 nm was found to afford (Z)-4-(1-naphthylmethylene)-5(4H)-oxazolone derivatives (Z)-2, (E)-2, alkyl-substituted thiols 3, and (E)-1 without forming any thio-radical-derived products. An analysis of the substituent and solvent effects on the reactivity of 1 and the product distribution demonstrated that the heterolytic C(=O)-S bond cleavage products 2 and 3 are not derived from the long-lived acylium and thiolate ions but from the protonated oxazolone/thiolate ion pair. The latter intermediates were assumed to be formed by the sulfur-assisted nucleophilic addition of the N-acyl carbonyl oxygen to the thioester carbonyl carbon in the excited state, followed by the elimination of the thiolate ion from the resulting adducts.
• Benzylidene-Oxazolones as Molecular Photoswitches
  作者：Marina Blanco-Lomas、Pedro J. Campos、Diego Sampedro

  DOI：10.1021/ol301741g

  日期：2012.9.7

  The synthesis and photochemical study of a family of molecular switches inspired by the green fluorescent protein (UP) chromophore is presented. These compounds can be easily synthesized, and their photophysical properties may be tuned. Due to their efficient photoisomerization and high stability, these compounds can be switched on/off by using light and heat or light with different wavelengths.