5-(2-methyl-1,3-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate | 1245824-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-methyl-1,3-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate
• 英文别名: [5-(2-methyl-1,3-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] N,N-diethylcarbamate
• CAS: 1245824-56-9
• 化学式: C₂₂H₃₄BNO₆
• 分子量: 419.326
• InChiKey: HVCVPTPUVYBUNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(2-methyl-1,3-dioxan-2-yl)phenyl N,N-diethylcarbamate 、 联硼酸频那醇酯 在 Ir(OMe)(cod) on silica-supported bridgehead monophosphine 作用下， 以 正己烷 为溶剂， 反应 24.0h， 以99%的产率得到5-(2-methyl-1,3-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate
  参考文献：
  名称：

  Rh-Catalyzed Ortho-Selective C–H Borylation of N-Functionalized Arenes with Silica-Supported Bridgehead Monophosphine Ligands

  摘要：

  Supported phosphine-Rh systems, prepared in situ from silica-supported bridgehead monophosphines and [Rh(OH)(cod)]2, have enabled ortho-selective C-H borylation for a range of arenes containing nitrogen-based directing groups. The regioselectivity was excellent with various N-directing groups, including saturated and unsaturated N-heterocycles, tert-aminoalkyl groups, and iminetype C-N double bonds. The reaction showed significant tolerance toward steric repulsion around the reacting C-H bond. This Rh catalysis complements the Jr-catalyzed orthoborylation, which is effective for arenes with oxygen-based directing groups.

  DOI：

  10.1021/ja208364a

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.