1,5-bis-(2,6-dimethylphenyl)-1,4-pentadiyn-3-one | 503309-98-6

• 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: 1,5-bis-(2,6-dimethylphenyl)-1,4-pentadiyn-3-one
• 英文别名: 1,5-Bis(2,6-dimethylphenyl)penta-1,4-diyn-3-one
• CAS: 503309-98-6
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: DVXOESUXBFYNLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-bis-(2,6-dimethylphenyl)-1,4-pentadiyn-3-one 在 sodium tetrahydroborate 、 sodium ethanolate 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以22%的产率得到2,6-bis(2,6-dimethylphenyl)thiapyran-4-one
  参考文献：
  名称：

  A Comparison of Linear Optical Properties and Redox Properties in Chalcogenopyrylium Dyes Bearing Ortho-Substituted Aryl Substituents and tert-Butyl Substituents

  摘要：

  A series of thiapyrylium pentamethine dyes (4 and 12-15) bearing 2,2'-di-tert-butyl-6,6'-diphenyl, 2,2'-di-tert-butyl-6,6'-bis(2,6-dimethylphenyl), 2,2'-di-tert-butyl-6,6'-bis(2-methylphenyl), 2,2',6,6'-tetrakis(2,6-dimethylphenyl), and 2,2',6,6'-tetrakis(2-methylphenyl) substituents, respectively, were prepared and their linear optical properties and electrochemical redox properties were measured and compared to thiapyrylium pentamethine dyes 3 and 5. The tert-butyl and 2,6-dimethylphenyl substituents give nearly identical chromophores with respect to values of lambda(max), molar extinction coefficients (epsilon), bandwidths at half-height (v(1/2)), and lack of absorption in the visible spectrum. The 2-methylphenyl substituent imparts linear optical properties that are intermediate between those of the tert-butyl and phenyl substituents. The 2,6-dimethylphenyl and 2-methylphenyl substituents impart greater oxidative stability based on anodic shifts in oxidation potential.

  DOI：

  10.1021/jo026645u
• 作为产物：
  描述：

  2,6-二甲基溴苯 在 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 1,5-bis-(2,6-dimethylphenyl)-1,4-pentadiyn-3-one
  参考文献：
  名称：

  A Comparison of Linear Optical Properties and Redox Properties in Chalcogenopyrylium Dyes Bearing Ortho-Substituted Aryl Substituents and tert-Butyl Substituents

  摘要：

  A series of thiapyrylium pentamethine dyes (4 and 12-15) bearing 2,2'-di-tert-butyl-6,6'-diphenyl, 2,2'-di-tert-butyl-6,6'-bis(2,6-dimethylphenyl), 2,2'-di-tert-butyl-6,6'-bis(2-methylphenyl), 2,2',6,6'-tetrakis(2,6-dimethylphenyl), and 2,2',6,6'-tetrakis(2-methylphenyl) substituents, respectively, were prepared and their linear optical properties and electrochemical redox properties were measured and compared to thiapyrylium pentamethine dyes 3 and 5. The tert-butyl and 2,6-dimethylphenyl substituents give nearly identical chromophores with respect to values of lambda(max), molar extinction coefficients (epsilon), bandwidths at half-height (v(1/2)), and lack of absorption in the visible spectrum. The 2-methylphenyl substituent imparts linear optical properties that are intermediate between those of the tert-butyl and phenyl substituents. The 2,6-dimethylphenyl and 2-methylphenyl substituents impart greater oxidative stability based on anodic shifts in oxidation potential.

  DOI：

  10.1021/jo026645u

文献信息

• A Comparison of Linear Optical Properties and Redox Properties in Chalcogenopyrylium Dyes Bearing Ortho-Substituted Aryl Substituents and <i>tert</i>-Butyl Substituents
  作者：Jagannath Panda、Peter R. Virkler、Michael R. Detty

  DOI：10.1021/jo026645u

  日期：2003.3.1

  A series of thiapyrylium pentamethine dyes (4 and 12-15) bearing 2,2'-di-tert-butyl-6,6'-diphenyl, 2,2'-di-tert-butyl-6,6'-bis(2,6-dimethylphenyl), 2,2'-di-tert-butyl-6,6'-bis(2-methylphenyl), 2,2',6,6'-tetrakis(2,6-dimethylphenyl), and 2,2',6,6'-tetrakis(2-methylphenyl) substituents, respectively, were prepared and their linear optical properties and electrochemical redox properties were measured and compared to thiapyrylium pentamethine dyes 3 and 5. The tert-butyl and 2,6-dimethylphenyl substituents give nearly identical chromophores with respect to values of lambda(max), molar extinction coefficients (epsilon), bandwidths at half-height (v(1/2)), and lack of absorption in the visible spectrum. The 2-methylphenyl substituent imparts linear optical properties that are intermediate between those of the tert-butyl and phenyl substituents. The 2,6-dimethylphenyl and 2-methylphenyl substituents impart greater oxidative stability based on anodic shifts in oxidation potential.