2,N,N,-diethylcarbamyloxyphenyl boronic acid | 103698-26-6

• 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: 2,N,N,-diethylcarbamyloxyphenyl boronic acid
• 英文别名: [2-(diethylcarbamoyloxy)phenyl]boronic Acid
• CAS: 103698-26-6
• 化学式: C₁₁H₁₆BNO₄
• 分子量: 237.063
• InChiKey: HZDUWQDOLDTYML-UHFFFAOYSA-N

物化性质

• 熔点：
  162-165 °C
• 沸点：
  398.8±48.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,N,N,-diethylcarbamyloxyphenyl boronic acid 在 四(三苯基膦)钯 盐酸 、 lithium aluminium tetrahydride 、 Jones’ reagent 、 sodium 、 sodium carbonate 、 Merrifield resin 作用下， 以 丙酮 为溶剂， 反应 96.0h， 生成 苯并[c]苯并吡喃-6-酮
  参考文献：
  名称：

  The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes

  摘要：

  The synthesis of the titled compounds by Suzuki-Miyaura cross coupling on Merrifield resin - Leznoff acetal - linked halo benzaldehydes followed by mild acid hydrolysis is reported; synthetic utility for heterocycles based on solution phase Directed ortho Metalation chemistry is demonstrated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00779-5
• 作为产物：
  描述：

  苯基二乙基氨基甲酸酯 在 四甲基乙二胺 、 仲丁基锂 、 硼酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以82%的产率得到2,N,N,-diethylcarbamyloxyphenyl boronic acid
  参考文献：
  名称：

  Strategies towards the Synthesis of 6‐N,N‐Diethylcarbamyloxy‐1,4‐dimethoxy‐ 7‐naphthylboronic Acid

  摘要：

  After acetylation, condensation between Danishefsky's diene and benzoquinone afforded a stable methoxytriacetoxydihydronaphthalene intermediate, which was subsequently transformed by the Snieckus DOM protocol into the regiospecific 7-naphthylboronic acid.

  DOI：

  10.1080/00397910701542962

文献信息

• Selective <i>Ortho</i> and Benzylic Functionalization of Secondary and Tertiary <i>p</i>-Tolylsulfonamides. <i>Ipso</i>-Bromo Desilylation and Suzuki Cross-Coupling Reactions
  作者：Stephen L. MacNeil、O. B. Familoni、Victor Snieckus

  DOI：10.1021/jo001402s

  日期：2001.6.1

  Kinetic vs thermodynamic deprotonation studies on secondary and tertiary sulfonamides 1 and 2 using n-BuLi have been carried out. While both 1 and 2 show kinetic ortho-metalation, thermodynamic conditions lead to ortho and benzylic deprotonation, respectively (Figures 1 and 2). Metalation of 1 using the n-BuLi/KOtBu superbase led to regioselective benzylic metalation (Figure 4); LDA deprotonation was

  已使用n-BuLi对仲磺酰胺1和叔磺酰胺2进行了动力学与热力学去质子研究。虽然1和2均显示动力学原位金属化，但热力学条件分别导致原位和苄基去质子化（图1和2）。使用n-BuLi / KOtBu超碱金属化1会导致区域选择性苄基金属化（图4）；还简要探讨了LDA的去质子化。所开发条件的应用允许合成多种磺酰胺产物5a-e，6a-e，7a，b和8a-e。异丙基-溴脱甲硅基反应得到磺酰胺9a，b，而铃木的交叉偶联反应得到联芳基磺酰胺11a-c。
• Synthetic connections to the aromatic directed metalationreaction. Unsymmetrical biaryls by palladium-catalyzed cross coupling of directed metalation-derived arylboronic acids with aryl halides
  作者：M.J. Sharp、V. Snieckus

  DOI：10.1016/s0040-4039(00)95108-6

  日期：1985.1

  The arylboronic acids 2 and 4 derived by directed ortho metalation of benzamides and carbamates, undergo an efficient palladium-catalyzed cross coupling reaction with a variety of aryl halides to yield unsymmetrical biaryls and heterobiaryls (Table).

  通过苯甲酰胺和氨基甲酸酯的直接邻位金属化衍生的芳基硼酸2和4与各种芳基卤化物进行有效的钯催化的交叉偶联反应，以产生不对称的联芳基和杂联芳基（表）。
• Readily available catalysts for demanding Suzuki–Miyaura couplings under mild conditions
  作者：Oleg M. Demchuk、Katarzyna Kapłon、Liliana Mazur、Dorota Strzelecka、K. Michał Pietrusiewicz

  DOI：10.1016/j.tet.2016.08.087

  日期：2016.10

  realised in a high yield starting from simple substrates in easily affordable conditions. In combination with a palladium source, the obtained ligand formed a highly active catalyst mediating sterically demanding Suzuki–Miyaura coupling reactions in aqueous media even at 60 °C and with no need to protect the reaction mixture by an inert gas.

  从简单的底物开始，在容易负担得起的条件下，以高收率实现了位阻和富电子的双齿双膦单膦联芳基配体Sym -Phos的C，P型络合的直接合成。与钯源结合，所得配体形成了高活性催化剂，即使在60°C的温度下，也能在水介质中介导空间要求严格的Suzuki-Miyaura偶联反应，而无需用惰性气体保护反应混合物。
• Dihydrothiophenes as precursors to fused quinolines, quinolones and coumarins via o-quinodimethane intermediates
  作者：Lindsay A. White、Richard C. Storr

  DOI：10.1016/0040-4020(95)01099-8

  日期：1996.2

  5-dihydrothiophene is a convenient starting point for synthesis of a range of 3,4- and 2,3-quinoline and quinolone and coumarin fused dihydrothiophene dioxides. With the exception of the 2,3-quinoline derivatives these all lose sulfur dioxide on thermolysis to give the corresponding o-quinodimethanes which can be intercepted in Diels-Alder reactions.

  3-甲氧羰基-4-酮-2,5-二氢噻吩是合成一系列3,4-和2,3-喹啉，喹诺酮和香豆素稠合的二氢噻吩二氧化物的便利起点。除2，3-喹啉衍生物外，所有这些均在热解时损失二氧化硫，得到相应的邻喹啉二甲烷，其可在狄尔斯-阿尔德反应中被拦截。
• Tricotet, Thomas; Fleming, Patricia; Cotter, Juliet, Journal of the American Chemical Society, 2009, vol. 131, p. 3142 - 3143
  作者：Tricotet, Thomas、Fleming, Patricia、Cotter, Juliet、Hogan, Anne-Marie L.、Strohmann, Carsten、et al.

  DOI：——

  日期：——