(R)-2-triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl
• 英文别名: 2-(Trifluoromethanesulfonyloxy)-2'-(4'-methoxybenzyloxy)-1,1'-binaphthyl；[1-[2-[(4-methoxyphenyl)methoxy]naphthalen-1-yl]naphthalen-2-yl] trifluoromethanesulfonate
• 化学式: C₂₉H₂₁F₃O₅S
• 分子量: 538.544
• InChiKey: HSDAOUBZTCUFGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl 在 盐酸 、 palladium diacetate 、 4 A molecular sieve 、 caesium carbonate 、 三乙胺 、 双(2-二苯基磷苯基)醚 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 19.0h， 生成 (R)-2-amino-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl
  参考文献：
  名称：

  Preparation of 2-amino-2′-hydroxy-1,1′-binaphthyl and N-arylated 2-amino-1,1′-binaphthyl derivatives via palladium-catalyzed amination

  摘要：

  Palladium-catalyzed amination reactions were carried out with 2-triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl (5) and benzophenone imine followed by hydrolysis of the imine and hydrogenolysis of the benzyl protecting group to afford 2-amino-2'-hydroxy-1,1'-binaphthyl (1). Arylamines were also coupled successfully with 5 under similar conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02642-2
• 作为产物：
  描述：

  (R)-1,1'-Bi-2-naphthol 在 正丁基锂 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.67h， 生成 (R)-2-triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl
  参考文献：
  名称：

  Preparation of 2-amino-2′-hydroxy-1,1′-binaphthyl and N-arylated 2-amino-1,1′-binaphthyl derivatives via palladium-catalyzed amination

  摘要：

  Palladium-catalyzed amination reactions were carried out with 2-triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl (5) and benzophenone imine followed by hydrolysis of the imine and hydrogenolysis of the benzyl protecting group to afford 2-amino-2'-hydroxy-1,1'-binaphthyl (1). Arylamines were also coupled successfully with 5 under similar conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02642-2

文献信息

• Arylamine synthesis
  申请人：Massachusetts Institute of Technology

  公开号：US06323366B1

  公开（公告）日：2001-11-27

  The present invention provides a method for the preparation of a wide range of primary arylamines. The arylamines are prepared in two efficient, straightforward transformations: 1) an activated aryl group and an imine group are combined, in the presence of a transition metal catalyst, under conditions wherein the transition metal catalyst catalyzes the formation of a carbon-nitrogen bond between the activated carbon of the arene and the imine nitrogen; and 2) the resulting N-aryl imine is transformed, via any of a number of standard protocols, to the primary arylamine. The method of the invention may also be exploited in the preparation of vinylamines.

  本发明提供了一种制备广泛范围的主要芳胺的方法。这些芳胺是通过两种高效、直接的转化制备的：1）在过渡金属催化剂的存在下，将活化的芳基和亚胺基结合在一起，在过渡金属催化剂催化的条件下，在芳烃的活化碳和亚胺氮之间催化形成碳-氮键；2）通过任何一种标准方案将产生的N-芳基亚胺转化为主要芳胺。该发明的方法还可用于制备乙烯胺。
• IMPROVED ARYLAMINE SYNTHESIS
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP1100774B1

  公开（公告）日：2004-01-21
• US6323366B1
  申请人：——

  公开号：US6323366B1

  公开（公告）日：2001-11-27
• [EN] IMPROVED ARYLAMINE SYNTHESIS<br/>[FR] SYNTHESE D'ARYLAMINE AMELIOREE
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2000005199A1

  公开（公告）日：2000-02-03

  The present invention provides a process for the preparation of a wide range of primary arylamines. The arylamines are prepared in two efficient, straightforward transformations: 1) an activated aryl group and an imine group are combined, in the presence of a transition metal catalyst, under conditions wherein the transition metal catalyst catalyzes the formation of a carbon-nitrogen bond between the activated carbon of the arene and the imine nitrogen; and 2) the resulting N-aryl imine is transformed, via any of a number of standard protocols, to the primary arylamine. The process of the invention may also be exploited in the preparation of vinylamines.
• Preparation of 2-amino-2′-hydroxy-1,1′-binaphthyl and N-arylated 2-amino-1,1′-binaphthyl derivatives via palladium-catalyzed amination
  作者：Robert A. Singer、Stephen L. Buchwald

  DOI：10.1016/s0040-4039(98)02642-2

  日期：1999.2

  Palladium-catalyzed amination reactions were carried out with 2-triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl (5) and benzophenone imine followed by hydrolysis of the imine and hydrogenolysis of the benzyl protecting group to afford 2-amino-2'-hydroxy-1,1'-binaphthyl (1). Arylamines were also coupled successfully with 5 under similar conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.