1-[2-(Diphenylphosphinothioylamino)naphthalen-1-yl]naphthalen-2-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[2-(Diphenylphosphinothioylamino)naphthalen-1-yl]naphthalen-2-amine
• 化学式: C₃₂H₂₅N₂PS
• 分子量: 500.604
• InChiKey: BYDWMELPACNHBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [1,1’-联萘]-2,2’-二胺 、 氯化二苯基硫磷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以92%的产率得到1-[2-(Diphenylphosphinothioylamino)naphthalen-1-yl]naphthalen-2-amine
  参考文献：
  名称：

  手性铜（I）联萘硫代磷酰胺或联萘硒代磷酰胺配体体系催化的二烷基锌和二苯基锌对映体的对映选择性共轭加成反应。

  摘要：

  二烷基锌或二苯基锌向烯酮的对映选择性共轭加成反应是在室温（20摄氏度）或0摄氏度下通过铜（I）-轴向手性二萘基硫代磷酰胺或二萘基硒代磷酰胺配体体系催化的，以高收率得到迈克尔加成物，具有优异的ee收率。环状和非环状烯酮。此处实现的对映选择性和反应速率是迄今为止将铜催化的共轭物添加至烯酮中的最佳结果之一。根据（31）P NMR和（13）C NMR光谱学研究表明，该系列手性磷酰胺是一种新型的S，N-二齿配体。还研究了这种不对称共轭加成系统的机理。我们发现这些手性配体中的磷酰胺的酸性质子在活性物种的形成中起着重要作用。在先前文献的基础上已经提出了双金属催化方法。产物ee和配体ee的线性效应进一步表明，活性物质是带有单个配体[Cu（I）：配体1：1]的单体Cu（I）配合物。

  DOI：

  10.1002/chem.200400254

文献信息

• Highly Enantioselective Allylation of Arylaldehydes Catalyzed by a Silver(I)-Chiral Binaphthylthiophosphoramide
  作者：Chun-Jiang Wang、Min Shi

  DOI：10.1002/ejoc.200300099

  日期：2003.8

  diphenylthiophosphoramide L2 prepared from diphenylthiophosphinic chloride and ?-(+)-N-ethyl-1,1'-binaphthyl-2,2'-diamine 2 was used as a catalytic chiral ligand in the siver(I)-catalyzed enantioselective allylation reaction of arylaldehydes with allyltribuyltin to furnish high ee (up to 98%) of the homoallylic alcohols.

  由二苯基硫代次膦酰氯和 α-(+)-N-乙基-1,1'-联萘-2,2'-二胺 2 制备的手性二苯基硫代磷酰胺 L2 在银 (I) 催化的对映选择性烯丙基化反应中用作催化手性配体芳基醛与烯丙基三烷基锡的反应可提供高 ee（高达 98%）的高烯丙醇。
• Enantioselective Conjugate Addition of Dialkylzinc and Diphenylzinc to Enones Catalyzed by a Chiral Copper(I) Binaphthylthiophosphoramide or Binaphthylselenophosphoramide Ligand System
  作者：Min Shi、Chun-Jiang Wang、Wen Zhang

  DOI：10.1002/chem.200400254

  日期：2004.11.5

  The enantioselective conjugate addition of dialkylzinc or diphenylzinc to enones was catalyzed by a copper(I)-axially chiral binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system at room temperature (20 degrees C) or 0 degrees C, affording the Michael adducts in high yields with excellent ee for cyclic and acyclic enones. The enantioselectivity and reaction rate achieved here are

  二烷基锌或二苯基锌向烯酮的对映选择性共轭加成反应是在室温（20摄氏度）或0摄氏度下通过铜（I）-轴向手性二萘基硫代磷酰胺或二萘基硒代磷酰胺配体体系催化的，以高收率得到迈克尔加成物，具有优异的ee收率。环状和非环状烯酮。此处实现的对映选择性和反应速率是迄今为止将铜催化的共轭物添加至烯酮中的最佳结果之一。根据（31）P NMR和（13）C NMR光谱学研究表明，该系列手性磷酰胺是一种新型的S，N-二齿配体。还研究了这种不对称共轭加成系统的机理。我们发现这些手性配体中的磷酰胺的酸性质子在活性物种的形成中起着重要作用。在先前文献的基础上已经提出了双金属催化方法。产物ee和配体ee的线性效应进一步表明，活性物质是带有单个配体[Cu（I）：配体1：1]的单体Cu（I）配合物。
• The Catalytic Asymmetric Addition of Diethylzinc toN-(Diphenylphosphinoyl) Imines Catalyzed by Cu(OTf)2-ChiralN-(Binaphthyl-2-yl)thiophosphoramide Ligands
  作者：Min Shi、Chun-Jiang Wang

  DOI：10.1002/adsc.200303041

  日期：2003.8

  Chiral N-(binaphthyl-2-yl)thiophosphoramide L7 [O,O-diethyl 2′-(ethylamino)-1,1′-binaphthyl-2-ylamidothiophosphate] prepared from the reaction of diethyl chlorothiophosphate with (R)-(+)-N-ethyl-1,1′-binaphthyl-2,2′-diamine was used as a catalytic chiral ligand in the first Cu(OTf)2-promoted catalytic asymmetric addition of diethylzinc to N-(diphenylphosphinoyl) imines in which ~85% ee can be realized

  手性ñ - （联萘-2-基）硫代磷酰胺L7 [ O，O-二乙基-2' - （乙基氨基）-1,1'-联萘-2- ylamidothiophosphate]从二氯代硫代磷酸酯与反应制备（[R ）- （+ ）-N-乙基-1,1'-联萘-2,2'-二胺在第一个Cu（OTf）2促进的二乙基锌向N-（二苯基膦酰基）亚胺的催化不对称加成中用作催化手性配体可以实现〜85％ee。
• Chiral diphenylthiophosphoramides: a new class of chiral ligands for the silver(I)-promoted enantioselective allylation of aldehydes
  作者：Min Shi、Wen-Sheng Sui

  DOI：10.1016/s0957-4166(99)00580-7

  日期：2000.2

  Chiral C-2-symmetric diphenylthiophosphoramides 1 and 2 were prepared in high yields from the reaction of diphenylthiophosphinic chloride with (1R,2R)-(-)-1,2-diaminocyclohexane and (1R,2R)-(+)- 1,2-diphenylethylenediamine, respectively. Another novel chiral ligand 4 was prepared from reaction of diphenylthiophosphinic chloride with (R)-(+)-1,1'-binaphthyl-2,2'-diamine using butyllithium as a base. They were used as catalytic chiral ligands in the silver(I)-promoted enantioselective allylation reaction of aldehydes with allyltributyltin. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Chiral Binaphthylthiophosphoramide−Cu(I)-Catalyzed Asymmetric Addition of Diethylzinc to <i>N</i>-Sulfonylimines
  作者：Chun-Jiang Wang、Min Shi

  DOI：10.1021/jo034269n

  日期：2003.8.1

  In the presence of a catalytic amount of chiral binaphthylthiophosphoramide L2 (6 mol %) and Cu(I) (3 mol %), the asymmetric addition of diethylzinc to N-sulfonylimines could be achieved in good yields with moderate to high ee (63-93% ee) at 0 degreesC in toluene. A novel chiral binaphthylthiophosphoramide ligand system for this asymmetric addition reaction has been explored.