6-[2-(methoxymethoxy)-3-methylphenyl]-2-N,2-N,4-N,4-N-tetramethyl-1,3,5-triazine-2,4-diamine | 1392406-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-[2-(methoxymethoxy)-3-methylphenyl]-2-N,2-N,4-N,4-N-tetramethyl-1,3,5-triazine-2,4-diamine
• CAS: 1392406-84-6
• 化学式: C₁₆H₂₃N₅O₂
• 分子量: 317.391
• InChiKey: MTRUORGWUJOFFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[2-(methoxymethoxy)-3-methylphenyl]-2-N,2-N,4-N,4-N-tetramethyl-1,3,5-triazine-2,4-diamine 在 盐酸 、 水 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-6-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：

  、 二甲胺 以 四氢呋喃 、 正己烷 、 水 、 甲苯 为溶剂， 以4.41 g的产率得到6-[2-(methoxymethoxy)-3-methylphenyl]-2-N,2-N,4-N,4-N-tetramethyl-1,3,5-triazine-2,4-diamine
  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

文献信息

• Synthetic Routes to Fluorescent Dyes Exhibiting Large Stokes Shifts
  作者：Sandra Rihn、Pascal Retailleau、Antoinette De Nicola、Gilles Ulrich、Raymond Ziessel

  DOI：10.1021/jo301059u

  日期：2012.10.19

  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.