3,5-Dimethyl-4-nitrophenetol | 52177-27-2

• 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: 3,5-Dimethyl-4-nitrophenetol
• 英文别名: 5-ethoxy-1,3-dimethyl-2-nitrobenzene
• CAS: 52177-27-2
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: DGWKUEPMHISJLU-UHFFFAOYSA-N

物化性质

• 沸点：
  310.0±37.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-Dimethyl-4-nitrophenetol 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 硫酸 、 氢溴酸 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 3.83h， 生成 2,6-二甲基-2,5-环己二烯-1,4-二酮
  参考文献：
  名称：

  Direct observation of the cyclopropene-vinylcarbene rearrangement. Matrix isolation of bicyclo[3.1.0]hexa-3,5-dien-2-ones

  摘要：

  4-Oxocyclohexa-2,5-dienylidenes 4b-g have been generated in argon matrices at 10 K by visible-light irradiation of the corresponding quinone diazides 5. Carbenes 4 have been characterized by IR and UV-vis spectroscopy and by their characteristic thermal reaction with molecular oxygen. On irradiation into the longest-wavelength absorption (420-700 nm), carbenes 4c-g rearrange to give the highly strained bicyclo[3.1.0]hexa-3,5-dien-2-ones 3c-g, while 4b is photostable under the same conditions. The photochemical 4 --> 3 rearrangement is completely reversible: infrared irradiation or visible light irradiation (lambda > 470 nm) of the cyclopropenes 3 lead back to triplet carbenes 4 quantitatively. In addition, several of the 1,3-bridged cyclopropenes 3 undergo a thermal rearrangement to give carbenes 4. This indicates that the highly strained cyclopropenes 3 are thermodynamically less stable than the corresponding carbenes 4 and kinetically only stabilized by a shallow energy barrier. Even under the conditions of matrix isolation at cryogenic temperatures, cyclopropenes 3 are metastable compounds.

  DOI：

  10.1021/jo00031a009
• 作为产物：
  描述：

  硝基甲烷 、 4-Ethoxy-2,6-dimethylpyrylium tetrafluoroborate 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以72%的产率得到3,5-Dimethyl-4-nitrophenetol
  参考文献：
  名称：

  Direct observation of the cyclopropene-vinylcarbene rearrangement. Matrix isolation of bicyclo[3.1.0]hexa-3,5-dien-2-ones

  摘要：

  4-Oxocyclohexa-2,5-dienylidenes 4b-g have been generated in argon matrices at 10 K by visible-light irradiation of the corresponding quinone diazides 5. Carbenes 4 have been characterized by IR and UV-vis spectroscopy and by their characteristic thermal reaction with molecular oxygen. On irradiation into the longest-wavelength absorption (420-700 nm), carbenes 4c-g rearrange to give the highly strained bicyclo[3.1.0]hexa-3,5-dien-2-ones 3c-g, while 4b is photostable under the same conditions. The photochemical 4 --> 3 rearrangement is completely reversible: infrared irradiation or visible light irradiation (lambda > 470 nm) of the cyclopropenes 3 lead back to triplet carbenes 4 quantitatively. In addition, several of the 1,3-bridged cyclopropenes 3 undergo a thermal rearrangement to give carbenes 4. This indicates that the highly strained cyclopropenes 3 are thermodynamically less stable than the corresponding carbenes 4 and kinetically only stabilized by a shallow energy barrier. Even under the conditions of matrix isolation at cryogenic temperatures, cyclopropenes 3 are metastable compounds.

  DOI：

  10.1021/jo00031a009

文献信息

• 一种酰胺衍生物及其制备方法和在药学上的 应用
  申请人：四川海思科制药有限公司

  公开号：CN106928126B

  公开（公告）日：2019-12-20

  本发明提供了一种酰胺衍生物及其制备方法和在药学上的应用，其中该酰胺衍生物化合物选自以下等的结构之一，所述化合物可以用来制备局部麻醉或镇痛领域药物：
• Direct observation of the cyclopropene-vinylcarbene rearrangement. Matrix isolation of bicyclo[3.1.0]hexa-3,5-dien-2-ones
  作者：Goetz Bucher、Wolfram Sander

  DOI：10.1021/jo00031a009

  日期：1992.2

  4-Oxocyclohexa-2,5-dienylidenes 4b-g have been generated in argon matrices at 10 K by visible-light irradiation of the corresponding quinone diazides 5. Carbenes 4 have been characterized by IR and UV-vis spectroscopy and by their characteristic thermal reaction with molecular oxygen. On irradiation into the longest-wavelength absorption (420-700 nm), carbenes 4c-g rearrange to give the highly strained bicyclo[3.1.0]hexa-3,5-dien-2-ones 3c-g, while 4b is photostable under the same conditions. The photochemical 4 --> 3 rearrangement is completely reversible: infrared irradiation or visible light irradiation (lambda > 470 nm) of the cyclopropenes 3 lead back to triplet carbenes 4 quantitatively. In addition, several of the 1,3-bridged cyclopropenes 3 undergo a thermal rearrangement to give carbenes 4. This indicates that the highly strained cyclopropenes 3 are thermodynamically less stable than the corresponding carbenes 4 and kinetically only stabilized by a shallow energy barrier. Even under the conditions of matrix isolation at cryogenic temperatures, cyclopropenes 3 are metastable compounds.