4-Methyl-2-phenyl-1-phenylmethoxybenzimidazole | 161958-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-Methyl-2-phenyl-1-phenylmethoxybenzimidazole
• CAS: 161958-74-3
• 化学式: C₂₁H₁₈N₂O
• 分子量: 314.387
• InChiKey: NPNBIGLIOAFVNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Methyl-2-phenyl-1-phenylmethoxybenzimidazole 在 palladium on activated charcoal 氢气 作用下， 反应 0.5h， 生成 4-methyl-2-phenyl-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents

  摘要：

  N-Alkoxy-, N-aryloxy- and N-allyloxybenzimidazoles (prepared using tandem N-alkylation, heterocyclisation and O-alkylation with in situ alkylating agent) can be selectively O-deprotected and then independently realkylated to provide a protocol For diversification with differentiated substituents at C2 and on oxygen. In addition, carboxamide functionalised derivatives 8 are amenable to staged interruption of the tandem reaction, allowing sequential additions of two different bases and alkylating agents directly affording 9. This 'start-stop-start' tandem process also facilitates diversification to analogues bearing different C2 and N-alkoxy substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00935-2
• 作为产物：
  描述：

  AR-甲基-AR-硝基苯胺 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以98%的产率得到4-Methyl-2-phenyl-1-phenylmethoxybenzimidazole
  参考文献：
  名称：

  Efficient One-Pot Conversion of 6-Methyl-2-nitroaniline into 1-Alkyloxy-2-alkyl-4-methyl-, 1-Benzyloxy-2-phenyl-4-Methyl-, and 1-Allyloxy-4-methyl-2-vinyl-benzimidazole

  摘要：

  6-Methyl-2-nitroaniline reacts with alkyl, benzyl and allyl halides and NaH as base, to afford 1-alkoxy-2-alkyl-, 1-benzyloxy-2-aryl- and 1-allyloxy-2-vinyl-benzimidazoles in good to excellent yields (73-98%), via a novel one-pot N-alkylation-heterocyclization-O-alkylation sequence.

  DOI：

  10.1080/00397919508013418

文献信息

• Gardiner John M., Loyns Colin R., Synth. Commun, 25 (1995) N 6, S 819-827
  作者：Gardiner John M., Loyns Colin R.

  DOI：——

  日期：——
• Efficient One-Pot Conversion of 6-Methyl-2-nitroaniline into 1-Alkyloxy-2-alkyl-4-methyl-, 1-Benzyloxy-2-phenyl-4-Methyl-, and 1-Allyloxy-4-methyl-2-vinyl-benzimidazole
  作者：John M. Gardiner、Colin R. Loyns

  DOI：10.1080/00397919508013418

  日期：1995.3

  6-Methyl-2-nitroaniline reacts with alkyl, benzyl and allyl halides and NaH as base, to afford 1-alkoxy-2-alkyl-, 1-benzyloxy-2-aryl- and 1-allyloxy-2-vinyl-benzimidazoles in good to excellent yields (73-98%), via a novel one-pot N-alkylation-heterocyclization-O-alkylation sequence.
• Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents
  作者：John M Gardiner、Jonathan Procter

  DOI：10.1016/s0040-4039(01)00935-2

  日期：2001.7

  N-Alkoxy-, N-aryloxy- and N-allyloxybenzimidazoles (prepared using tandem N-alkylation, heterocyclisation and O-alkylation with in situ alkylating agent) can be selectively O-deprotected and then independently realkylated to provide a protocol For diversification with differentiated substituents at C2 and on oxygen. In addition, carboxamide functionalised derivatives 8 are amenable to staged interruption of the tandem reaction, allowing sequential additions of two different bases and alkylating agents directly affording 9. This 'start-stop-start' tandem process also facilitates diversification to analogues bearing different C2 and N-alkoxy substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.