1-[(1-methyl-1H-indol-3-yl)methyl]-1H-1,2,3-benzotriazole | 161533-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[(1-methyl-1H-indol-3-yl)methyl]-1H-1,2,3-benzotriazole
• 英文别名: 1-[(1-methylindol-3-yl)methyl]benzotriazole
• CAS: 161533-36-4
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: CRFPEWAHCOOXGS-UHFFFAOYSA-N

物化性质

• 沸点：
  510.5±33.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(1-methyl-1H-indol-3-yl)methyl]-1H-1,2,3-benzotriazole 在 正丁基锂 、 四氯化钛 、 铜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 0.5h， 生成 3-((Z)-2-cyclohexyl-1-ethenyl)-1-methyl-1H-indole
  参考文献：
  名称：

  Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

  摘要：

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

  DOI：

  10.1021/jo980616v
• 作为产物：
  描述：

  1-甲基吲哚 、 1H-苯并三唑-1-甲醇 以 甲苯 为溶剂， 反应 40.0h， 以40%的产率得到1-[(1-methyl-1H-indol-3-yl)methyl]-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  A Versatile Synthesis of 3-Substituted Indoles

  摘要：

  A variety of 3-substituted indoles are prepared from 1-methyl-3-(benzotriazol-1-ylalkyl)indoles (1), which are readily available either from the condensation of 3-methylindole with N-(benzotriazol-1-ylalkyl)carbamates or from the alkylation and silylation of lithiated 1-methyl-3-(benzotriazol-1-ylmethyl)indole (2).

  DOI：

  10.1080/00397919508011388

文献信息

• General and Efficient Insertions of Carbons Carrying Aryl and Heteroaryl Groups:  Synthesis of α-Aryl- and α-Heteroaryl-Substituted Ketones
  作者：Alan R. Katritzky、Dorin Toader、Linghong Xie

  DOI：10.1021/jo960841h

  日期：1996.1.1

  iazoles 1 with n-BuLi underwent addition to aliphatic and aromatic aldehydes and cyclic and acyclic ketones. Subsequent in situ thermal rearrangements of the intermediates in the presence of zinc bromide provided one-carbon chain-extended or ring-expanded alpha-aryl- and alpha-heteroaryl-substituted ketones 2 in moderate to excellent yields in simple one-pot operations with excellent regioselectivity

  由多种1-（芳基甲基）-和1-（杂芳基甲基）苯并三唑1与正丁基锂的锂化反应所形成的阴离子要加入脂族和芳族醛以及环状和非环状酮中。中间体在溴化锌存在下的随后原位热重排可在简单的一锅操作中以中等至优异的产率提供一碳链扩展或环扩展的α-芳基-和α-杂芳基取代的酮2在大多数情况下具有区域选择性。在1-（4-甲氧基苄基）苯并三唑（1e）与XC（6）H（4）COPh的插入反应中研究了取代基对相对迁移速率的影响。较小的负Hammett rho（+）值（-0.92）表明，重排通过早期的，类似试剂的电子不足的过渡态进行。
• General and Efficient Carbon Insertion Route to One-Carbon-Homologated .alpha.-Aryl, .alpha.-Alkenyl, .alpha.-Alkoxy, and .alpha.-Phenylthio Alkyl Ketones
  作者：Alan R. Katritzky、Linghong Xie、Dorin Toader、Larisa Serdyuk

  DOI：10.1021/ja00153a032

  日期：1995.12
• Katritzky, Alan R.; Wang, Junquan; Henderson, Scott A., Heterocycles, 1998, vol. 48, # 8, p. 1567 - 1574
  作者：Katritzky, Alan R.、Wang, Junquan、Henderson, Scott A.

  DOI：——

  日期：——
• Efficient Syntheses of Substituted Carbazoles and Cyclopent[<i>b</i>]indoles from 1-Methyl-3-(benzotriazol-1-ylmethyl)indole
  作者：Alan R. Katritzky、Guifen Zhang、Linghong Xie、Ion Ghiviriga

  DOI：10.1021/jo9604954

  日期：1996.1.1

  1-Methyl-3-(benzotriazol-1-ylmethyl)indole (1)undergoes lithiation and 1,4-addition with a variety of alpha,beta-unsaturated ketones and aldehydes. Subsequent treatment with an acidic resin in refluxing 1,4-dioxane causes intramolecular cyclization followed by aromatization to furnish a wide range of 1.3-di-, 2,3-di- and 1,2,3-trisubstituted carbazoles 6a-j and 8 in moderate to excellent yields. NMR study is described to discriminate between structures of types 6 and 8 on the basis of H-1-C-13 long-range correlation. Treatment of 1 with styrenes in the presence of zinc bromide results in formal [3+2] cycloaddition to give cyclopent[b]indoles 14a-c in good yields. When 1 is first lithiated and reacts with electrophiles, the resulting alkylation products undergo similar [3+2] additions with styrenes to give 1-functionalized cyclopent[b]indoles 15 and 16 with a high degree of stereoselectivity.
• A General and Facile Synthesis of Heterocyclo[b]-Fused Carbazoles
  作者：Alan R. Katritzky、Linghong Xie

  DOI：10.1021/jo00117a022

  日期：1995.6

  1-Methyl-2-bromo-3-[(benzotriazol-1-yl)methyl]indole (2), available from the regio selective bromination of 1-methyl-3-[(benzotriazol-1-yl)methyl]in (1), undergoes halogen-lithium exchange with t-BuLi. The resulting carbanion 4 reacts with thiophene-3-carboxaldehyde, furan-3-carboxaldehyde, thiophene-2-carboxaldehyde, furan-2-carboxaldehyde, and indole-3-carboxaldehyde. Subsequent quenching with methyl iodide affords the corresponding methyl ether intermediates 6a-e in excellent yields. Refluxing intermediates 6a-e in 1,2,4-trichlorobenzene or 1,2-dichlorobenzene causes intramolecular cyclization followed by aromatization. 5-Methylthieno[3,2-b]carbazole (8a), 5-methylfuro[3,2-b]carbazole (8b), 5-methylthieno[2,3-b]carbazole (8c), 5-methylfuro[2,3-b]carbazole (8d), and 5,11-dimethylindolo[3,2-b]carbazole (8e) are thus obtained in 31-67% yields.