3-methoxy-6-oxo-6H-benzo[c]chromene-8-carbonitrile | 1403876-04-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-methoxy-6-oxo-6H-benzo[c]chromene-8-carbonitrile
• 英文别名: 3-Methoxy-6-oxobenzo[c]chromene-8-carbonitrile；3-methoxy-6-oxobenzo[c]chromene-8-carbonitrile
• CAS: 1403876-04-9
• 化学式: C₁₅H₉NO₃
• 分子量: 251.241
• InChiKey: LACGTPQATKGAJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-6-oxo-6H-benzo[c]chromene-8-carbonitrile 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.01h， 生成 methyl 4-cyano-2',4'-dimethoxy-[1,1'-biphenyl]-2-carboxylate
  参考文献：
  名称：

  Donor–acceptor biaryl lactones: pH induced molecular switches with intramolecular charge transfer modulation

  摘要：

  The physical properties of biaryl-containing compounds are known to be highly dependent on molecular geometry. We report the syntheses and fundamental spectroscopic study of two donor-acceptor biaryl lactone (6H-benzo[c]chromen-6-one) pH-driven switches. These compounds have been determined to rapidly and efficiently switch between two geometric states upon cycling of acidic or basic stimuli. The planar lactone state exhibits enhanced intramolecular charge transfer (ICT) between the donor and acceptor units which is instantly attenuated upon addition of basic stimuli. The resulting lactone cleavage enables aryl-aryl bond rotation thus decreasing the extent of conjugation between the rings. Each state is readily identifiable by the significant changes that occur in their respective UV-vis spectra and luminescent character, indicative of the facile modulation of extended conjugation by pH. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.016
• 作为产物：
  描述：

  methyl 4-cyano-2',4'-dimethoxy-[1,1'-biphenyl]-2-carboxylate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98.7%的产率得到3-methoxy-6-oxo-6H-benzo[c]chromene-8-carbonitrile
  参考文献：
  名称：

  Donor–acceptor biaryl lactones: pH induced molecular switches with intramolecular charge transfer modulation

  摘要：

  The physical properties of biaryl-containing compounds are known to be highly dependent on molecular geometry. We report the syntheses and fundamental spectroscopic study of two donor-acceptor biaryl lactone (6H-benzo[c]chromen-6-one) pH-driven switches. These compounds have been determined to rapidly and efficiently switch between two geometric states upon cycling of acidic or basic stimuli. The planar lactone state exhibits enhanced intramolecular charge transfer (ICT) between the donor and acceptor units which is instantly attenuated upon addition of basic stimuli. The resulting lactone cleavage enables aryl-aryl bond rotation thus decreasing the extent of conjugation between the rings. Each state is readily identifiable by the significant changes that occur in their respective UV-vis spectra and luminescent character, indicative of the facile modulation of extended conjugation by pH. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.016

文献信息

• Donor–acceptor biaryl lactones: pH induced molecular switches with intramolecular charge transfer modulation
  作者：Erik J. Carlson、Asia Marie S. Riel、Bart J. Dahl

  DOI：10.1016/j.tetlet.2012.09.016

  日期：2012.11

  The physical properties of biaryl-containing compounds are known to be highly dependent on molecular geometry. We report the syntheses and fundamental spectroscopic study of two donor-acceptor biaryl lactone (6H-benzo[c]chromen-6-one) pH-driven switches. These compounds have been determined to rapidly and efficiently switch between two geometric states upon cycling of acidic or basic stimuli. The planar lactone state exhibits enhanced intramolecular charge transfer (ICT) between the donor and acceptor units which is instantly attenuated upon addition of basic stimuli. The resulting lactone cleavage enables aryl-aryl bond rotation thus decreasing the extent of conjugation between the rings. Each state is readily identifiable by the significant changes that occur in their respective UV-vis spectra and luminescent character, indicative of the facile modulation of extended conjugation by pH. (C) 2012 Elsevier Ltd. All rights reserved.