4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate | 1245824-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate
• 英文别名: [4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] N,N-diethylcarbamate
• CAS: 1245824-47-8
• 化学式: C₁₈H₂₈BNO₅
• 分子量: 349.235
• InChiKey: NAJJXXTWXJBDFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 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77%的产率得到3-甲氧基苯硼酸频哪醇酯
  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：

  (4-甲氧基苯基)N,N-二乙基氨基甲酸酯 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.42h， 生成 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 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

• Directed Ortho Borylation of Phenol Derivatives Catalyzed by a Silica-Supported Iridium Complex
  作者：Kenji Yamazaki、Soichiro Kawamorita、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ol101493m

  日期：2010.9.17

  The directed ortho borylation of phenol derivatives protected with an N,N-diethylcarbamoyl group was efficiently catalyzed by an immobilized monophosphine-Ir system, which was prepared in situ from [Ir(OMe)(cod)](2) and a silica-supported, compact phosphine. The utility of the carbamoyloxy group as a leaving group for metal-catalyzed cross-coupling reactions was demonstrated by its utilization in the synthesis of a terphenyl derivative.
• 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.