2,5-Bis(N,N-diethylamino)-4-<(trimethylsilyl)ethynyl>phenol | 172216-14-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-Bis(N,N-diethylamino)-4-<(trimethylsilyl)ethynyl>phenol
• 英文别名: 2,5-Bis(diethylamino)-4-(2-trimethylsilylethynyl)phenol
• CAS: 172216-14-7
• 化学式: C₁₉H₃₂N₂OSi
• 分子量: 332.561
• InChiKey: UAQKQTIPCOJBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-Bis(N,N-diethylamino)-4-<(trimethylsilyl)ethynyl>phenol 在 copper(l) iodide 、 15-冠醚-5 氢氧化钾 、 四甲基乙二胺 、 氧气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇甲醚 为溶剂， 反应 72.0h， 生成 2-butoxy-5-[4-[4-butoxy-2,5-bis(diethylamino)phenyl]buta-1,3-diynyl]-1-N,1-N,4-N,4-N-tetraethylbenzene-1,4-diamine
  参考文献：
  名称：

  Probing Delocalization Across Alkyne-Containing Linkages: Synthesis and Cyclic Voltammetry of Bridged Phenylenediamines

  摘要：

  This paper presents the synthesis of N,N,N',N'-tetraethyl-1,4-phenylenediamines bridged by ethynylphenyl-ethynyl and diethynyl linkages. These compounds are of interest to determine if the N,N,N',N'-tetraethyl-1,4-phenylenediamines exhibit delocalized mixed oxidation states when oxidized electrochemically. 1-Butoxy-2,5-bis(N,N-diethylamino)-4-ethynylbenzene was a key intermediate, and nucleophilic addition of lithium (trimethylsilyl)acetylide to 2,5-bis(N,N-diethylamino)-1,4-benzoquinone provided an efficient synthesis of this compound. This intermediate was then assembled into the redox assemblies of interest in high yield by use of palladium-catalyzed cross-coupling and copper-catalyzed oxidative home-coupling protocols. Cyclic voltammetry of these compounds indicate that the N,N,N',N'-tetraethyl-1,4-phenylenediamine redox units behave independently and that the interactions are principally electrostatic. As a result, we conclude that the electrochemically generated radical cations and dications are highly localized.

  DOI：

  10.1021/jo00127a011
• 作为产物：
  描述：

  2,5-Bis-diaethylamino-p-benzochinon 、 三甲基乙炔基硅 在 正丁基锂 、 三甲基氯硅烷 、 溶剂黄146 、 锌 作用下， 生成 2,5-Bis(N,N-diethylamino)-4-<(trimethylsilyl)ethynyl>phenol
  参考文献：
  名称：

  Probing Delocalization Across Alkyne-Containing Linkages: Synthesis and Cyclic Voltammetry of Bridged Phenylenediamines

  摘要：

  This paper presents the synthesis of N,N,N',N'-tetraethyl-1,4-phenylenediamines bridged by ethynylphenyl-ethynyl and diethynyl linkages. These compounds are of interest to determine if the N,N,N',N'-tetraethyl-1,4-phenylenediamines exhibit delocalized mixed oxidation states when oxidized electrochemically. 1-Butoxy-2,5-bis(N,N-diethylamino)-4-ethynylbenzene was a key intermediate, and nucleophilic addition of lithium (trimethylsilyl)acetylide to 2,5-bis(N,N-diethylamino)-1,4-benzoquinone provided an efficient synthesis of this compound. This intermediate was then assembled into the redox assemblies of interest in high yield by use of palladium-catalyzed cross-coupling and copper-catalyzed oxidative home-coupling protocols. Cyclic voltammetry of these compounds indicate that the N,N,N',N'-tetraethyl-1,4-phenylenediamine redox units behave independently and that the interactions are principally electrostatic. As a result, we conclude that the electrochemically generated radical cations and dications are highly localized.

  DOI：

  10.1021/jo00127a011

文献信息

• Probing Delocalization Across Alkyne-Containing Linkages: Synthesis and Cyclic Voltammetry of Bridged Phenylenediamines
  作者：Qin Zhou、Timothy M. Swager

  DOI：10.1021/jo00127a011

  日期：1995.11

  This paper presents the synthesis of N,N,N',N'-tetraethyl-1,4-phenylenediamines bridged by ethynylphenyl-ethynyl and diethynyl linkages. These compounds are of interest to determine if the N,N,N',N'-tetraethyl-1,4-phenylenediamines exhibit delocalized mixed oxidation states when oxidized electrochemically. 1-Butoxy-2,5-bis(N,N-diethylamino)-4-ethynylbenzene was a key intermediate, and nucleophilic addition of lithium (trimethylsilyl)acetylide to 2,5-bis(N,N-diethylamino)-1,4-benzoquinone provided an efficient synthesis of this compound. This intermediate was then assembled into the redox assemblies of interest in high yield by use of palladium-catalyzed cross-coupling and copper-catalyzed oxidative home-coupling protocols. Cyclic voltammetry of these compounds indicate that the N,N,N',N'-tetraethyl-1,4-phenylenediamine redox units behave independently and that the interactions are principally electrostatic. As a result, we conclude that the electrochemically generated radical cations and dications are highly localized.