(Z)-2-(4-methoxyphenyl)-4-(1-naphthylmethylene)-5(4H)-oxazolone | 425380-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-(4-methoxyphenyl)-4-(1-naphthylmethylene)-5(4H)-oxazolone
• 英文别名: (4Z)-2-(4-Methoxyphenyl)-4-[(naphthalen-1-YL)methylidene]-4,5-dihydro-1,3-oxazol-5-one；(4Z)-2-(4-methoxyphenyl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5-one
• CAS: 425380-61-6
• 化学式: C₂₁H₁₅NO₃
• 分子量: 329.355
• InChiKey: VKNILLMIDSQITM-UYRXBGFRSA-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：

  (Z)-2-(4-methoxyphenyl)-4-(1-naphthylmethylene)-5(4H)-oxazolone 在 TEA 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 生成 (E)-2-(4-anisoylamino)-N-methyl-3-(1-naphthyl)-2-propenamide
  参考文献：
  名称：

  Highly selective conversion of N-aroyl-α-dehydronaphthylalaninamides into 3,4-dihydrobenzoquinolinone derivatives via photoinduced intermolecular electron transfer

  摘要：

  The irradiation of substituted (Z)-N-aroyl-alpha-dehydronaphthylalaninamides [(Z)-1] in methanol containing triethylamine (TEA) with Pyrex-filtered light was found to give 3,4-dihydrobenzoquinolinone derivatives (2) in high yields along with minor amounts of 4,5-dihydrooxazole derivatives (3). Analysis of the substituent effects on product composition revealed that both the photoreactivity of 1 and the selectivity of 2 are decreased with increasing electron-withdrawing ability of the substituent introduced at the para-position on the N-benzoyl benzene ring. From the analysis of the dependence of the quantum yield for the formation of 2 on the TEA concentration, it was found that back electron transfer occurs efficiently within an (E)-1 anion radical-TEA cation radical pair intermediate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.096
• 作为产物：
  描述：

  1-萘甲醛 、 (4-甲氧基-苯甲酰氨基)-乙酸 在 sodium acetate 、 乙酸酐 作用下， 生成 (Z)-2-(4-methoxyphenyl)-4-(1-naphthylmethylene)-5(4H)-oxazolone
  参考文献：
  名称：

  通过光诱导电子转移引发的N-酰基-α-脱氢芳基丙氨酸烷基酯的环化反应，优先形成顺式-4,5-二氢恶唑衍生物

  摘要：

  从机理和合成的观点出发，研究了极性溶剂中烷基，芳基和酰基取代基对标题化合物（1）的光诱导电子转移引发的环化反应的影响。的照射（ż） - 1在含有三乙胺（TEA）的甲醇被发现，定量得到顺式-和反式-4,5-二氢恶唑衍生物（顺式- 2和反式- 2）。除了热力学考虑为对发光强度的电子转移和荧光猝灭在TEA，酰基和芳基取代基效应的存在和光反应1证实了形成（E）-芳基亚甲基自由基阴离子和（E）-N-酰基自由基阴离子中间体的连续电子转移反应的参与。还证实了后者中间体的环化最终导致2。这样的发现为选择性的基础顺- 2大大随的烷基和芳基取代基的空间体积增加1，可以得出结论，在的环化双基中间，前体的这些取代基对氢移的空间位阻2负责该中间体的动力学控制的氢转移。产物组成分析表明，质子性极性溶剂甲醇具有氢键合溶剂化能力，是最适合检测的光环化反应的溶剂。

  DOI：

  10.1016/j.tet.2007.08.089

文献信息

• Motohashi, Toyohisa; Maekawa, Kei; Kubo, Kanji, Heterocycles, 2002, vol. 57, # 2, p. 269 - 292
  作者：Motohashi, Toyohisa、Maekawa, Kei、Kubo, Kanji、Igarashi, Tetsutaro、Sakurai, Tadamitsu

  DOI：——

  日期：——
• Highly selective conversion of N-aroyl-α-dehydronaphthylalaninamides into 3,4-dihydrobenzoquinolinone derivatives via photoinduced intermolecular electron transfer
  作者：Kei Maekawa、Ayana Shinozuka、Michiko Naito、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2004.08.096

  日期：2004.11

  The irradiation of substituted (Z)-N-aroyl-alpha-dehydronaphthylalaninamides [(Z)-1] in methanol containing triethylamine (TEA) with Pyrex-filtered light was found to give 3,4-dihydrobenzoquinolinone derivatives (2) in high yields along with minor amounts of 4,5-dihydrooxazole derivatives (3). Analysis of the substituent effects on product composition revealed that both the photoreactivity of 1 and the selectivity of 2 are decreased with increasing electron-withdrawing ability of the substituent introduced at the para-position on the N-benzoyl benzene ring. From the analysis of the dependence of the quantum yield for the formation of 2 on the TEA concentration, it was found that back electron transfer occurs efficiently within an (E)-1 anion radical-TEA cation radical pair intermediate. (C) 2004 Elsevier Ltd. All rights reserved.
• Preferential formation of cis-4,5-dihydrooxazole derivatives via photoinduced electron transfer-initiated cyclization of N-acyl-α-dehydroarylalanine alkyl esters
  作者：Kei Maekawa、Norikazu Hishikawa、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2007.08.089

  日期：2007.11

  aryl, and acyl substituent effects on the photoinduced electron transfer-initiated cyclization reaction of the title compounds (1) were investigated in polar solvents from mechanistic and synthetic points of view. The irradiation of (Z)-1 in methanol containing triethylamine (TEA) was found to quantitatively give cis- and trans-4,5-dihydrooxazole derivatives (cis-2 and trans-2). In addition to thermodynamic

  从机理和合成的观点出发，研究了极性溶剂中烷基，芳基和酰基取代基对标题化合物（1）的光诱导电子转移引发的环化反应的影响。的照射（ż） - 1在含有三乙胺（TEA）的甲醇被发现，定量得到顺式-和反式-4,5-二氢恶唑衍生物（顺式- 2和反式- 2）。除了热力学考虑为对发光强度的电子转移和荧光猝灭在TEA，酰基和芳基取代基效应的存在和光反应1证实了形成（E）-芳基亚甲基自由基阴离子和（E）-N-酰基自由基阴离子中间体的连续电子转移反应的参与。还证实了后者中间体的环化最终导致2。这样的发现为选择性的基础顺- 2大大随的烷基和芳基取代基的空间体积增加1，可以得出结论，在的环化双基中间，前体的这些取代基对氢移的空间位阻2负责该中间体的动力学控制的氢转移。产物组成分析表明，质子性极性溶剂甲醇具有氢键合溶剂化能力，是最适合检测的光环化反应的溶剂。