1-(tert-butoxyformamido)-2,2-dibromo-1-(4-methoxyphenyl)-2-nitroethane | 1420742-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(tert-butoxyformamido)-2,2-dibromo-1-(4-methoxyphenyl)-2-nitroethane
• 英文别名: tert-butyl N-[2,2-dibromo-1-(4-methoxyphenyl)-2-nitroethyl]carbamate
• CAS: 1420742-57-9
• 化学式: C₁₄H₁₈Br₂N₂O₅
• 分子量: 454.115
• InChiKey: JHURWPZXRUSGMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氨基甲酸叔丁酯 在 potassium phosphate monohydrate 、 溴 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 1-(tert-butoxyformamido)-2,2-dibromo-1-(4-methoxyphenyl)-2-nitroethane
  参考文献：
  名称：

  Approach to Vicinal t-Boc-amino Dibromides via Catalytic Aminobromination of Nitrostyrenes without Using Chromatography and Recrystallization

  摘要：

  A 1.0 mol % amount of K3PO4 center dot 3H(2)O was found to catalyze aminohalogenation reaction of nitrostyrenes with N,N-dibromo-tert-butylcarbamate (t-Boc-NBr2) in a dichloroethane system. Good to excellent yields and complete regioselectivity have been achieved by taking advantage of the GAP workup without using traditional purification techniques such as column chromatography and recrystallization. A new mechanism is proposed involving radical and ionic catalytic cycles and an intramolecular migration.

  DOI：

  10.1021/jo302727v

文献信息

• Approach to Vicinal <i>t</i>-Boc-amino Dibromides via Catalytic Aminobromination of Nitrostyrenes without Using Chromatography and Recrystallization
  作者：Hao Sun、Jianlin Han、Padmanabha V. Kattamuri、Yi Pan、Guigen Li

  DOI：10.1021/jo302727v

  日期：2013.2.1

  A 1.0 mol % amount of K3PO4 center dot 3H(2)O was found to catalyze aminohalogenation reaction of nitrostyrenes with N,N-dibromo-tert-butylcarbamate (t-Boc-NBr2) in a dichloroethane system. Good to excellent yields and complete regioselectivity have been achieved by taking advantage of the GAP workup without using traditional purification techniques such as column chromatography and recrystallization. A new mechanism is proposed involving radical and ionic catalytic cycles and an intramolecular migration.