methyl (Z)-2-(4-cyanobenzoylamino)-3-(1-naphthyl)-2-propenoate | 708277-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (Z)-2-(4-cyanobenzoylamino)-3-(1-naphthyl)-2-propenoate
• 英文别名: methyl (Z)-2-[(4-cyanobenzoyl)amino]-3-naphthalen-1-ylprop-2-enoate
• CAS: 708277-12-7
• 化学式: C₂₂H₁₆N₂O₃
• 分子量: 356.381
• InChiKey: NQYLTEHCOQUCNR-MOSHPQCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-(4-cyanobenzoylamino)-3-(1-naphthyl)-2-propenoate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 cis-2-(4-cyanophenyl)-4-methoxycarbonyl-5-(1-naphthyl)-4,5-dihydrooxazole 、 trans-2-(4-cyanophenyl)-4-methoxycarbonyl-5-(1-naphthyl)-4,5-dihydrooxazole
  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
• 作为产物：
  描述：

  、 甲醇 在 TEA 作用下， 生成 methyl (Z)-2-(4-cyanobenzoylamino)-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

• 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。
• 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.