2-(4-Methoxyphenyl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5-one | 5523-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-Methoxyphenyl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5-one
• CAS: 5523-97-7
• 化学式: C₂₁H₁₅NO₃
• mdl: MFCD01539201
• 分子量: 329.355
• InChiKey: VKNILLMIDSQITM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Methoxyphenyl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5-one 、 甲醇 在 TEA 作用下， 生成 methyl (Z)-2-(4-methoxybenzoylamino)-3-(1-naphthyl)-2-propenoate
  参考文献：
  名称：

  Selective and efficient transformation of N-(4-substituted benzoyl)-α-dehydroarylalanine alkyl esters into 4,5-dihydrooxazole derivatives via photoinduced electron transfer

  摘要：

  The irradiation of N-(4-substituted benzoyl)-alpha-dehydroarylalanine alkyl esters (1) in methanol containing triethylamine (TEA) was found to quantitatively give cis- and trans-4,5-dihydrooxazole derivatives (2), which were described as being formed via electron transfer from TEA to the excited-state (E)-1 followed by kinetically-controlled cyclization of the (E)-1-derived anion radical. A product composition analysis showed that the cis-2/trans-2 composition ratio is greatly varied depending on the stereo-electronic properties of the substituents, the polarity of protic solvents and the concentration of TEA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.042

文献信息

• Selective and efficient transformation of N-(4-substituted benzoyl)-α-dehydroarylalanine alkyl esters into 4,5-dihydrooxazole derivatives via photoinduced electron transfer
  作者：Kei Maekawa、Takahiro Sasaki、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tetlet.2004.03.042

  日期：2004.4

  The irradiation of N-(4-substituted benzoyl)-alpha-dehydroarylalanine alkyl esters (1) in methanol containing triethylamine (TEA) was found to quantitatively give cis- and trans-4,5-dihydrooxazole derivatives (2), which were described as being formed via electron transfer from TEA to the excited-state (E)-1 followed by kinetically-controlled cyclization of the (E)-1-derived anion radical. A product composition analysis showed that the cis-2/trans-2 composition ratio is greatly varied depending on the stereo-electronic properties of the substituents, the polarity of protic solvents and the concentration of TEA. (C) 2004 Elsevier Ltd. All rights reserved.