5-[(diethylcarbamoyl)oxy]naphthalen-1-yl N,N-diethylcarbamate | 501104-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[(diethylcarbamoyl)oxy]naphthalen-1-yl N,N-diethylcarbamate
• 英文别名: [5-(diethylcarbamoyloxy)naphthalen-1-yl] N,N-diethylcarbamate
• CAS: 501104-82-1
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: AIORXGVYVNQGLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(diethylcarbamoyl)oxy]naphthalen-1-yl N,N-diethylcarbamate 在 二氯化双(三环己基膦)镍(II) 、 1,1,3,3-四甲基二硅氧烷 、 K₃PO₄ 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以82%的产率得到萘
  参考文献：
  名称：

  Cine Substitution of Arenes Using the Aryl Carbamate as a Removable Directing Group

  摘要：

  An efficient and controlled means to achieve a rare cine substitution of arenes is reported. The methodology relies on the strategic use of aryl O-carbamates as readily removable directing groups for arene functionallzation. The removal of aryl carbamates is achieved by employing an airstable Ni(II) precatalyst, along with an inexpensive reducing agent, to give synthetically useful yields across a range of substrates. The net cine substitution process offers a new strategy for analogue synthesis, which complements the well-established logic for achieving arene functionalization by ipso substitution.

  DOI：

  10.1021/ol301275u
• 作为产物：
  描述：

  1,5-二羟基萘 、 N,N-二乙基氯甲酰胺 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 mineral oil 为溶剂， 反应 20.0h， 以22%的产率得到5-[(diethylcarbamoyl)oxy]naphthalen-1-yl N,N-diethylcarbamate
  参考文献：
  名称：

  Cine Substitution of Arenes Using the Aryl Carbamate as a Removable Directing Group

  摘要：

  An efficient and controlled means to achieve a rare cine substitution of arenes is reported. The methodology relies on the strategic use of aryl O-carbamates as readily removable directing groups for arene functionallzation. The removal of aryl carbamates is achieved by employing an airstable Ni(II) precatalyst, along with an inexpensive reducing agent, to give synthetically useful yields across a range of substrates. The net cine substitution process offers a new strategy for analogue synthesis, which complements the well-established logic for achieving arene functionalization by ipso substitution.

  DOI：

  10.1021/ol301275u

文献信息

• Cine Substitution of Arenes Using the Aryl Carbamate as a Removable Directing Group
  作者：Tehetena Mesganaw、Noah F. Fine Nathel、Neil K. Garg

  DOI：10.1021/ol301275u

  日期：2012.6.1

  An efficient and controlled means to achieve a rare cine substitution of arenes is reported. The methodology relies on the strategic use of aryl O-carbamates as readily removable directing groups for arene functionallzation. The removal of aryl carbamates is achieved by employing an airstable Ni(II) precatalyst, along with an inexpensive reducing agent, to give synthetically useful yields across a range of substrates. The net cine substitution process offers a new strategy for analogue synthesis, which complements the well-established logic for achieving arene functionalization by ipso substitution.