2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-6-iodo-4-methylphenol | 1392406-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-6-iodo-4-methylphenol
• CAS: 1392406-80-2
• 化学式: C₁₄H₁₈IN₅O
• 分子量: 399.234
• InChiKey: GRKJOCOVRLDFPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-6-iodo-4-methylphenol 、 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 苯 为溶剂， 反应 240.0h， 以72.1 mg的产率得到2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-6-[2-(2,2-difluoro-4,6,8,10,12-pentamethyl-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-5-yl)ethynyl]-4-methylphenol
  参考文献：
  名称：

  Synthetic Routes to Fluorescent Dyes Exhibiting Large Stokes Shifts

  摘要：

  Derivatives of isomeric 2-(hydroxytolyl)-4,6-dimethylamino-1,3,5-triazines have been synthesized in high yields in a controlled manner using a multistep reaction sequence. Iodination of either 2-(1'-hydroxy-6'-methylphen-2'-yl)- or 2-(1'-hydroxy-4'-methylphen-2'-yl)-4,6-dimethylamino-1,3,5-triazine with ICl provides species differing in the positioning of the iodo group relative to the hydroxyl which readily undergo Suzuki, Sonogashira, and Heck reactions under Pd(0) catalysis. Thus, thienyl, bisthienyl, and 3,4-ethylenedioxythienyl groups have been directly grafted, while unsubstituted polycyclic aromatics such as pyrene and perylene have been linked via alkyne bridges, as have ethynyldifluoroborondipyrromethane (BODIPY) dyes prepared in situ. The presence of a hydrogen bond in the ground state involving the hydroxyl substituent has been established by proton NMR and several X-ray structure determinations. All of the new dyes with a simple substituent (phenyl, thienyl) exhibited a pronounced green fluorescence resulting from an intramolecular proton transfer:in:the excited state (ESIPT) which produces a large Stokes shift (> 10 000 cm(-1)). With other dyes, the fluorescence of the keto form responsible for the ESIPT process could be used as the.input energy in efficient intramolecular energy transfer processes. Replacing perylene with pyrene allowed reversal of the direction of energy transfer from the polyaromatic module to the keto form.

  DOI：

  10.1021/jo301059u
• 作为产物：
  描述：

  在 盐酸 、 水 、 一氯化碘 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-6-iodo-4-methylphenol
  参考文献：
  名称：

  Synthetic Routes to Fluorescent Dyes Exhibiting Large Stokes Shifts

  摘要：

  Derivatives of isomeric 2-(hydroxytolyl)-4,6-dimethylamino-1,3,5-triazines have been synthesized in high yields in a controlled manner using a multistep reaction sequence. Iodination of either 2-(1'-hydroxy-6'-methylphen-2'-yl)- or 2-(1'-hydroxy-4'-methylphen-2'-yl)-4,6-dimethylamino-1,3,5-triazine with ICl provides species differing in the positioning of the iodo group relative to the hydroxyl which readily undergo Suzuki, Sonogashira, and Heck reactions under Pd(0) catalysis. Thus, thienyl, bisthienyl, and 3,4-ethylenedioxythienyl groups have been directly grafted, while unsubstituted polycyclic aromatics such as pyrene and perylene have been linked via alkyne bridges, as have ethynyldifluoroborondipyrromethane (BODIPY) dyes prepared in situ. The presence of a hydrogen bond in the ground state involving the hydroxyl substituent has been established by proton NMR and several X-ray structure determinations. All of the new dyes with a simple substituent (phenyl, thienyl) exhibited a pronounced green fluorescence resulting from an intramolecular proton transfer:in:the excited state (ESIPT) which produces a large Stokes shift (> 10 000 cm(-1)). With other dyes, the fluorescence of the keto form responsible for the ESIPT process could be used as the.input energy in efficient intramolecular energy transfer processes. Replacing perylene with pyrene allowed reversal of the direction of energy transfer from the polyaromatic module to the keto form.

  DOI：

  10.1021/jo301059u