(R)-P,P-diphenyl-N-(phenyl(o-tolyl)methyl)phosphinic amide | 1190207-38-5

• 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)-P,P-diphenyl-N-(phenyl(o-tolyl)methyl)phosphinic amide
• 英文别名: N-[1-(2-methylphenyl)-1-phenylmethyl]-P,P-diphenylphosphinamide；(1R)-N-diphenylphosphoryl-1-(2-methylphenyl)-1-phenylmethanamine
• CAS: 1190207-38-5
• 化学式: C₂₆H₂₄NOP
• 分子量: 397.456
• InChiKey: KHOCWTLQHZTEHK-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  N-(2-methylbenzylidene)-P,P-diphenylphosphinamide 、 苯硼酸酐 在 acetylacetonatobis(ethylene)rhodium(I) 、 tert-butyl N-{1-(R)-[(2-(S)-bis(2-methylphenyl)phosphinomethyl)pyrrolidine-1-carbonyl]-2-methylpropyl}-carbamate 作用下， 以 1,4-二氧六环 、 丙醇 为溶剂， 反应 12.0h， 以86%的产率得到(R)-P,P-diphenyl-N-(phenyl(o-tolyl)methyl)phosphinic amide
  参考文献：
  名称：

  Steric Tuning of the Amidomonophosphane-Rhodium(I) Catalyst in Asymmetric Addition of Arylboroxines to N-Phosphinoyl Aldimines

  摘要：

  Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-phosphinoylaldi mines was realized by the steric tuning of a cliphenylphosphorus moiety to a di(o-tolyl) phosphorus moiety of a chiral amidomonophosphane. The presence of MS 4 A in a 5:1 solvent mixture of dioxane-propanol was essential to afford the corresponding diarylmethylamines in high yield.

  DOI：

  10.1021/ol901866y

文献信息

• A New Phosphine-Amine-Oxazoline Ligand for Ru-Catalyzed Asymmetric Hydrogenation of<i>N</i>-Phosphinylimines
  作者：Xiaochen Ma、Lin Qiao、Guixia Liu、Zheng Huang

  DOI：10.1002/cjoc.201800343

  日期：2018.12

  A series of chiral phosphine‐amine‐oxazoline (PAO) ligands with an NH moiety were synthesized and applied to the ruthenium‐catalyzed asymmetric hydrogenation of N‐phosphinylimines. The ligand bearing phenyl groups at the phosphorus moiety and isopropyl at the oxazoline moiety exhibits good activity and excellent enantioselectivity (up to 99% ee). This catalytic system provides an efficient and mild

  合成了一系列具有NH部分的手性膦-胺-恶唑啉（PAO）配体，并将其应用于钌催化的N-次膦亚胺的不对称氢化。在磷部分带有苯基且在恶唑啉部分带有异丙基的配体表现出良好的活性和优异的对映选择性（至多99％ee）。该催化体系提供了一种有效且温和的方法来获得对映体胺。
• Design and Synthesis of Chiral Diene Ligands for Rh^I -Catalyzed Enantioselective Arylation of <i>N</i> -DPP-protected Aldimines: Synthesis of the Antifungal Agent Bifonazole
  作者：Jin-Fong Syu、Huang-Ying Lin、Yu-Yi Cheng、Yao-Chu Tsai、Yi-Ching Ting、Ting-Shen Kuo、Damodar Janmanchi、Ping-Yu Wu、Julian P. Henschke、Hsyueh-Liang Wu

  DOI：10.1002/chem.201702509

  日期：2017.10.17

  carboxylic ester groups, or only with aryl groups, the addition reaction proceeded with high stereoselectivity. The protocol tolerated a range of N‐DPP‐aldimines and arylboronic acids, producing the desired optically active N‐DPP‐protected amines with yields between 31–99 % and with ee values up to 91–99 %. The synthetic utility of the method was demonstrated by the conversion of N‐DPP‐protected amine 3 ae into

  在本文中，我们描述了新型的双官能团，带有芳基和仲酰胺基的手性双环[2.2.1]庚二烯配体的设计和合成，并证明了它们在Rh I催化的芳基硼酸与N-二苯基膦基的对映选择性加成反应中的用途。（N -DPP）保护的亚胺。与包含被芳基和羧酸酯基团或仅被芳基取代的二烯配体的类似Rh I催化剂不同，加成反应以高立体选择性进行。该方案可耐受N -DPP-亚胺和芳基硼酸，产生所需的旋光性N‐DPP保护的胺，收率在31–99％之间，并且ee值高达91–99％。该方法的合成效用通过将N ‐DPP保护的胺3 ae转化为抗真菌剂联苯苄唑（13）得以证明。