4-[3-(Dibutylamino)-2-methylpropyl]-2-methoxyphenol | 1415746-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[3-(Dibutylamino)-2-methylpropyl]-2-methoxyphenol
• CAS: 1415746-49-4
• 化学式: C₁₉H₃₃NO₂
• 分子量: 307.477
• InChiKey: NTUORJBLCQWBRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丁香酚 、 一氧化碳 、 二正丁胺 在 methoxy(cyclooctadiene)rhodium(I) dimer 、 氢气 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲苯 为溶剂， 120.0 ℃ 、4.0 MPa 条件下， 反应 24.0h， 生成 4-[3-(Dibutylamino)-2-methylpropyl]-2-methoxyphenol 、 4-[4-(Dibutylamino)butyl]-2-methoxyphenol 、 3-(4-hydroxy-3-methoxyphenyl)-2-methylpropanal 、 4-(3-甲氧基-4-羟基-苯基)-丁醛
  参考文献：
  名称：

  Hydroaminomethylation of eugenol with di-n-butylamine catalyzed by rhodium complexes: Bringing light on the promoting effect of Brönsted acids

  摘要：

  The hydroaminomethylation of eugenol with di-n-butylamine was performed employing a bis[(1,5-ciclooctadiene)(mu-methoxy)rhodium(1)] as pre-catalyst. In the absence of phosphines, the catalyst was efficient in the process, but the regioselectivity for amines was poor. For phosphine-promoted catalyst, the chemoselectivity at the hydroformylation step improved, but the hydrogenation of enamine intermediates was hampered. The regioselectivity within the class of amines was surprisingly high (>96%) for the linear product. The addition of triflic acid (10-20 mol%) improved significantly the efficiency of HAM. Employing the 22'-bis((diphenylphosphino)methyl)-1,1'-binaphthyl as ancillary and triflic acid as a promoter, the linear product was obtained in up to 93% yield. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2012.08.033