1-(2-(benzyloxy)-3-nitrophenyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(2-(benzyloxy)-3-nitrophenyl)piperidine
• 英文别名: 1-(3-Nitro-2-phenylmethoxyphenyl)piperidine；1-(3-nitro-2-phenylmethoxyphenyl)piperidine
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: VRBMFXBRWHPWOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-(benzyloxy)-3-nitrophenyl)piperidine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3-氨基吩恶嗪酮
  参考文献：
  名称：

  Unexpected one pot C (aryl)–N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives

  摘要：

  2-Amino-6-nitrophenol derivatives 5A and 5B have been prepared from the bromonitro phenol derivative 4 using the Buchwald conditions. While attempting one pot reduction of nitro group and deprotection of phenolic benzyl group of the compounds 5A and 5B separately using Pd/C in methanol under H-2 atmosphere, an unexpected C(aryl)-N bond cleavage reaction had occurred which was followed by formation of a known compound Questiomycin A (2-amino-3H-phenoxazin-3-one) 1 from both the compounds. In the present study, the danger of deamination of Buchwald products 5A and 5B under the conditions of catalytic hydrogenation and the simultaneous formation of phenoxazine I is disclosed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.080
• 作为产物：
  描述：

  硝苯酚 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 溴 、 potassium carbonate 、 caesium carbonate 、 溶剂黄146 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 20.0h， 生成 1-(2-(benzyloxy)-3-nitrophenyl)piperidine
  参考文献：
  名称：

  Unexpected one pot C (aryl)–N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives

  摘要：

  2-Amino-6-nitrophenol derivatives 5A and 5B have been prepared from the bromonitro phenol derivative 4 using the Buchwald conditions. While attempting one pot reduction of nitro group and deprotection of phenolic benzyl group of the compounds 5A and 5B separately using Pd/C in methanol under H-2 atmosphere, an unexpected C(aryl)-N bond cleavage reaction had occurred which was followed by formation of a known compound Questiomycin A (2-amino-3H-phenoxazin-3-one) 1 from both the compounds. In the present study, the danger of deamination of Buchwald products 5A and 5B under the conditions of catalytic hydrogenation and the simultaneous formation of phenoxazine I is disclosed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.080

文献信息

• Unexpected one pot C (aryl)–N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives
  作者：Shaik Mustafa、K. Santhosh Reddy、M.S. Surendra Babu

  DOI：10.1016/j.tetlet.2015.09.080

  日期：2015.10

  2-Amino-6-nitrophenol derivatives 5A and 5B have been prepared from the bromonitro phenol derivative 4 using the Buchwald conditions. While attempting one pot reduction of nitro group and deprotection of phenolic benzyl group of the compounds 5A and 5B separately using Pd/C in methanol under H-2 atmosphere, an unexpected C(aryl)-N bond cleavage reaction had occurred which was followed by formation of a known compound Questiomycin A (2-amino-3H-phenoxazin-3-one) 1 from both the compounds. In the present study, the danger of deamination of Buchwald products 5A and 5B under the conditions of catalytic hydrogenation and the simultaneous formation of phenoxazine I is disclosed. (C) 2015 Elsevier Ltd. All rights reserved.