N-benzotriazol-1-ylmethyl-2-chloro-aniline | 62001-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-benzotriazol-1-ylmethyl-2-chloro-aniline
• 英文别名: n-(1h-1,2,3-Benzotriazol-1-ylmethyl)-2-chloroaniline；N-(benzotriazol-1-ylmethyl)-2-chloroaniline
• CAS: 62001-30-3
• 化学式: C₁₃H₁₁ClN₄
• 分子量: 258.71
• InChiKey: TYMCWBNPKBRJMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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-2-chloro-aniline 、 sodium S-butyl sulfothioate 在 三氢化钐 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以78%的产率得到N-(butylsulfanylmethyl)-2-chloroaniline
  参考文献：
  名称：

  A Novel Synthesis of Unsymmetrical α-Amino Sulfides via the Sm/ZnCl2 System in THF–Water

  摘要：

  通过1-(α-氨基烷基)苯并三唑与烷基硫代硫酸钠在THF-水中的Sm/ZnCl2体系催化下反应，可以合成非对称的α-氨基硫醚，产率中等至良好。

  DOI：

  10.1039/a904194j
• 作为产物：
  描述：

  1H-苯并三唑-1-甲醇 、 邻氯苯胺 以 乙醇 为溶剂， 以45%的产率得到N-benzotriazol-1-ylmethyl-2-chloro-aniline
  参考文献：
  名称：

  Milata; Kada; Zalibera, Bollettino Chimico Farmaceutico, 2001, vol. 140, # 4, p. 215 - 220

  摘要：

  DOI：

文献信息

• Benzotriazole Mediated Synthesis of Methylenebisanilines
  作者：Alan R. Katritzky、Xiangfu Lan、Jamshed N. Lam

  DOI：10.1055/s-1990-26873

  日期：——

  Methylenebisanilines and methylenebis(N,N-dialkylaniline)s are prepared by the reactions of 1-hydroxymethylbenzotriazole with anilines and with N,N-dialkylanilines under acidic conditions. Isolation of the intermediate 4-(benzotriazol-1-ylmethyl)anilines and the N,N-dialkyl analogues and their reactions with anilines allow the efficient preparation of both symmetrical and unsymmetrical members of both product classes.

  亚甲基双苯胺和亚甲基双(N,N-二烷基苯胺)是由 1-羟甲基苯并三唑与苯胺和 N,N-二烷基苯胺在酸性条件下反应制备的。通过分离中间体 4-(苯并三唑-1-基甲基)苯胺和 N,N-二烷基类似物以及它们与苯胺的反应，可以有效地制备这两类产品的对称和不对称成员。
• 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。
• Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)
  作者：Gordon W. Rewcastle、Brian D. Palmer、Ellen M. Dobrusin、David W. Fry、Alan J. Kraker、William A. Denny

  DOI：10.1021/jm00039a016

  日期：1994.6

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.
• Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+, J. Med. Chem, 37 (1994) N 13, S 2033-2042
  作者：Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+

  DOI：——

  日期：——
• Milata; Kada; Zalibera, Bollettino Chimico Farmaceutico, 2001, vol. 140, # 4, p. 215 - 220
  作者：Milata、Kada、Zalibera、Belicova

  DOI：——

  日期：——