(R)-(+)-N-[1-(2-chlorophenyl)propyl]-P,P-diphenylphosphinoylamide | 919349-88-5

• 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: (R)-(+)-N-[1-(2-chlorophenyl)propyl]-P,P-diphenylphosphinoylamide
• 英文别名: N-[(1R)-1-(2-chlorophenyl)propyl]-P,P-diphenylphosphinic amide；(R)-N-[1-(2-chlorophenyl)propyl]-P,P-diphenylphosphinoylamide；N-[1-(2-chlorophenyl)propyl]-P,P-diphenylphosphinoylamide；Phosphinic amide, N-[(1R)-1-(2-chlorophenyl)propyl]-P,P-diphenyl-；(1R)-1-(2-chlorophenyl)-N-diphenylphosphorylpropan-1-amine
• CAS: 919349-88-5
• 化学式: C₂₁H₂₁ClNOP
• 分子量: 369.831
• InChiKey: PZOIJIPOVCVWFB-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  P,P-diphenyl-N-(2-chlorophenylmethylene)phosphinic amide 、 diethylzinc 在 copper(II) bis(trifluoromethanesulfonate) (R_a)-(+)-(2'-EtNH-[1,1']binaphth-2-yl)-NH-P(S)(OPh)2 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以82%的产率得到(R)-(+)-N-[1-(2-chlorophenyl)propyl]-P,P-diphenylphosphinoylamide
  参考文献：
  名称：

  三氟甲磺酸铜（II）-手性（2'-乙氨基-[1,1']联萘基-2-基）-硫代磷酰胺酸O， O'-二芳基酯配体催化的二乙基锌与二苯基膦酰基亚胺的不对称加成反应

  摘要：

  手性binaphthylthiophosphoramide L1从反应制备O，O-二苯基磷酰氯与（[R ）- （+） - ñ -乙基- 1,1'-联萘-2,2'-二胺用作催化手性配体由三氟甲磺酸铜（II）促进的二乙基膦酸向二苯基膦酰基亚胺的不对称加成反应，得到相应的加合物，收率90-98％ee，在温和条件下收率良好。

  DOI：

  10.1002/adsc.200606128

文献信息

• METHOD OF ENANTIOSELECTIVE ADDITION TO IMINES
  申请人：UANG Biing-Jiun

  公开号：US20120004441A1

  公开（公告）日：2012-01-05

  The present invention relates to a method of enantioselective addition to imines, including: reacting R 3 CH═NY with R 4 ZnR 5 in the presence of a compound represented by the following formula (I), in which Y, R 1 , R 2 , R 3 , R 4 and R 5 are defined the same as the specification. Accordingly, the present invention can prepare secondary amines in high yields and enantiomeric excess by the above-mentioned method.

  本发明涉及一种对亚胺进行对映选择性加成的方法，包括：在以下式(I)所代表的化合物存在下，将R3CH═NY与R4ZnR5反应，其中Y、R1、R2、R3、R4和R5的定义与规范相同。因此，本发明可以通过上述方法高产率和对映过量地制备二级胺。
• Asymmetric, Catalytic Synthesis of α-Chiral Amines Using a Novel Bis(phosphine) Monoxide Chiral Ligand
  作者：Alessandro A. Boezio、Julien Pytkowicz、Alexandre Côté、André B. Charette

  DOI：10.1021/ja038291+

  日期：2003.11.1

  We have shown that Me-DuPHOS monoxide (BozPHOS) is a very effective ligand in the copper-catalyzed addition of dialkylzinc to N-phosphinoylimines providing access to alpha-chiral amines. The new ligand is particularly effective for the addition of the lesser reactive dimethylzinc. The major advantages of this process are high yields, broad substrate scope, and high enantioselectivities with low catalyst

  我们已经证明 Me-DuPHOS 一氧化 (BozPHOS) 在铜催化下将二烷基锌加成到 N-膦亚胺中是一种非常有效的配体，提供了获得 α-手性胺的途径。新配体对于添加反应性较低的二甲基锌特别有效。该方法的主要优点是收率高、底物范围广、对映选择性高、催化剂负载量低（3 mol%）。
• Enantioselective Addition of Dialkylzinc to Aromatic Aldimines Mediated by Camphor-Derived Chiral β-Amino Alcohols
  作者：Wei-Ming Huang、Biing-Jiun Uang

  DOI：10.1002/asia.201403240

  日期：2015.4

  The enantioselective addition of diethylzinc or dimethylzinc to N‐(diphenylphosphinoyl)imines mediated by 1 or 2 could be achieved in high yields (70–97 %) and enantioselectivities (85–98 % ee). The catalytic loading of 1 or 2 a could be reduced to 10 mol % for methylation or ethylation of imines in high yields and enantioselectivities (79–96 %) when the reaction was conducted in the presence of 1

  在1或2介导的N-（二苯基膦酰基）亚胺中对二乙基锌或二甲基锌的对映选择性加成（70-97％）和对映选择性（85-98％ee）可以实现。当反应在1.8当量甲醇的存在下进行时，亚胺的甲基化或乙基化反应可以将1或2 a的催化负载降低至10 mol％，从而获得高收率和对映选择性（79-96％）。ñ单取代的氨基醇比他们更高的诱导对映选择性ñ，ñ在我们的催化体系双取代同类。
• Chiral ferrocenyl amidophosphine ligand for highly enantioselective addition of diethylzinc to N-diphenylphosphinoylimines
  作者：Min-Can Wang、Cui-Lian Xu、Fu Cheng、Xue Ding

  DOI：10.1016/j.tet.2006.10.015

  日期：2006.12

  The asymmetric addition of diethylzine to N-diphenylphosphinoylimines afforded N-diphenylphosphinoylamides with enantioselectivity of up to 90% ee in the presence of a catalytic amount of chiral ligand (S)-N-ferrocenoyl-2-[(diphenylphosphino)methyll-pyrrolidine 13 (7 mol %) and Cu(OTf)(2) (15 mol %). The remarkable improvement of enantioselectivities, as compared with the same type of chiral ligand 6, could be explained by the unique structure of ferrocenyl amidophosphine ligand combining with the reactive intermediate of this addition reaction. (c) 2006 Elsevier Ltd. All rights reserved.
• US8461371B2
  申请人：——

  公开号：US8461371B2

  公开（公告）日：2013-06-11