N-(benzotriazol-1-ylmethyl)-1-naphthylamine | 134627-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(benzotriazol-1-ylmethyl)-1-naphthylamine
• 英文别名: N-(benzotriazol-1-ylmethyl)naphthalen-1-amine
• CAS: 134627-19-3
• 化学式: C₁₇H₁₄N₄
• 分子量: 274.325
• InChiKey: ABYVUCOEJMCTGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(benzotriazol-1-ylmethyl)-1-naphthylamine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 1-<1-(methylamino)-2-naphthyl>-2-methyl-1-propanol
  参考文献：
  名称：

  Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. 17. Substitution of N-methyl-1- and N-methyl-2-naphthylamine and side-chain functionalization of o-toluidine

  摘要：

  N-Methyl-1-naphthylamine is readily converted into a range of 2-substituted derivatives in one-pot sequences, using carbon dioxide for NH protection. Similarly, N-methyl-2-naphthylamine yields 3-substituted derivatives in the first direct preparation of 2,3-disubstituted naphthalenes. The intermediate lithium carbamates are further lithiated by tert-butyllithium at the 2-position for N-methyl-1-naphthylamine and at the 3-position for N-methyl-2-naphthylamine and then reacted with an electrophile; the products undergo acid-catalyzed decarboxylation during workup. omicron-Toluidine is converted into its methyl-functionalized derivatives in a similar way, except that 2 equiv of tert-butyllithium are used for the further lithiation of the intermediate lithium carbamate.

  DOI：

  10.1021/jo00017a012
• 作为产物：
  描述：

  T406石油添加剂 、 聚合甲醛 、 1-萘胺 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 N-(benzotriazol-1-ylmethyl)-1-naphthylamine
  参考文献：
  名称：

  N-环丙基-1-氨基萘将光电子注入DNA

  摘要：

  含有N-环丙基-1-氨基萘（cAN）或N的DNA已经开发了作为光诱导电子供体的-甲基-1-氨基萘（mAN），以研究DNA双链体中的电子注入和电荷重组过程。与SCE相比，光激发的氨基萘（ANs）的氧化电位估计约为-3.0 V，该电位高至足以诱导DNA碱基的单电子还原。已使用凝胶电泳检查了在AN拴系的DNA双链体中光诱导的过量电子转移，但对于cAN和mAN拴系的DNA而言，表观电子转移效率几乎相同。环丙基取代对电荷分离效率的边际影响表明，接触自由基离子对中的电荷重组比环丙烷开环更快更有效。

  DOI：

  10.1016/j.jphotochem.2011.01.025

文献信息

• Reactions of<i>N</i>-aryl-1<i>H</i>-benzotriazolyl-1-methanamines with allyl trimethylsilanes. A facile route to trialkylsilane tetrahydroquinolines
  作者：Alan R. Katritzky、Xilin Cui、Qiuhe Long

  DOI：10.1002/jhet.5570360207

  日期：1999.3

  N-Aryl-1H-benzotriazolyl-1-methanamines 1, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo Lewis acid assisted reactions with allyl trimethylsilanes to give 4-(trimethylsilyl)methyl-1,2,3,4-tetrahydroquinolines 2 in good to high yields.

  N-芳基-1 H-苯并三唑基-1-甲胺1易于从苯胺与甲醛和苯并三唑的缩合反应中进行，与路易斯烯酸三甲基硅烷进行路易斯酸辅助反应，得到4-（三甲基甲硅烷基）甲基-1,2,3,4 -四氢喹啉2高至高收率。
• Photoinduced electron injection into DNA by N-cyclopropyl-1-aminonaphthalene
  作者：Takeo Ito、Tsukasa Uchida、Kazuhito Tanabe、Hisatsugu Yamada、Sei-ichi Nishimoto

  DOI：10.1016/j.jphotochem.2011.01.025

  日期：2011.3

  one-electron reduction of DNA bases. Photoinduced excess electron transfer in the AN-tethered DNA duplexes has been examined using gel electrophoresis, but the apparent electron-transfer efficiencies were almost the same for both of the cAN- and the mAN-tethered DNA. The marginal effect of cyclopropyl substitution on the efficiency of charge separation suggests that charge recombination in the contact radical

  含有N-环丙基-1-氨基萘（cAN）或N的DNA已经开发了作为光诱导电子供体的-甲基-1-氨基萘（mAN），以研究DNA双链体中的电子注入和电荷重组过程。与SCE相比，光激发的氨基萘（ANs）的氧化电位估计约为-3.0 V，该电位高至足以诱导DNA碱基的单电子还原。已使用凝胶电泳检查了在AN拴系的DNA双链体中光诱导的过量电子转移，但对于cAN和mAN拴系的DNA而言，表观电子转移效率几乎相同。环丙基取代对电荷分离效率的边际影响表明，接触自由基离子对中的电荷重组比环丙烷开环更快更有效。
• Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. 17. Substitution of N-methyl-1- and N-methyl-2-naphthylamine and side-chain functionalization of o-toluidine
  作者：Alan R. Katritzky、Michael Black、Wei Qiang Fan

  DOI：10.1021/jo00017a012

  日期：1991.8

  N-Methyl-1-naphthylamine is readily converted into a range of 2-substituted derivatives in one-pot sequences, using carbon dioxide for NH protection. Similarly, N-methyl-2-naphthylamine yields 3-substituted derivatives in the first direct preparation of 2,3-disubstituted naphthalenes. The intermediate lithium carbamates are further lithiated by tert-butyllithium at the 2-position for N-methyl-1-naphthylamine and at the 3-position for N-methyl-2-naphthylamine and then reacted with an electrophile; the products undergo acid-catalyzed decarboxylation during workup. omicron-Toluidine is converted into its methyl-functionalized derivatives in a similar way, except that 2 equiv of tert-butyllithium are used for the further lithiation of the intermediate lithium carbamate.