N-(2-Nitro-1-phenylethyl)-P,P-diphenylphosphinic amide | 807610-78-2

• 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: N-(2-Nitro-1-phenylethyl)-P,P-diphenylphosphinic amide
• 英文别名: N-(2-nitro-1-phenylethyl)diphenylphosphinic amide；N-diphenylphosphoryl-2-nitro-1-phenylethanamine
• CAS: 807610-78-2
• 化学式: C₂₀H₁₉N₂O₃P
• 分子量: 366.356
• InChiKey: RWYNJSBZVMJJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-Nitro-1-phenylethyl)-P,P-diphenylphosphinic amide 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到N-diphenylphosphoryl-1-phenylethane-1,2-diamine
  参考文献：
  名称：

  The First Catalytic Asymmetric Nitro-Mannich-Type Reaction Promoted by a New Heterobimetallic Complex

  摘要：

  The best ratio is 1:1:3 for the components Yb, K, and binaphthol in the new heterobimetallic complex, which efficiently catalyzes an asymmetric nitro-Mannich-type reaction. The desired nitro-Mannich products 2 are obtained with up to 91 % ee starting from N-phosphinoyl imines 1.

  DOI：

  10.1002/(sici)1521-3773(19991203)38:23<3504::aid-anie3504>3.0.co;2-e
• 作为产物：
  描述：

  二苯基磷酰胺 在 (R)-binaphthol 、 ytterbium(III) isopropoxide 、 potassium tert-butylate 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 35.0h， 生成 N-(2-Nitro-1-phenylethyl)-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  The First Catalytic Asymmetric Nitro-Mannich-Type Reaction Promoted by a New Heterobimetallic Complex

  摘要：

  The best ratio is 1:1:3 for the components Yb, K, and binaphthol in the new heterobimetallic complex, which efficiently catalyzes an asymmetric nitro-Mannich-type reaction. The desired nitro-Mannich products 2 are obtained with up to 91 % ee starting from N-phosphinoyl imines 1.

  DOI：

  10.1002/(sici)1521-3773(19991203)38:23<3504::aid-anie3504>3.0.co;2-e

文献信息

• [EN] ASYMMETRIC MICHAEL AND ALDOL ADDITION USING BIFUNCTIONAL CINCHONA-ALKALOID-BASED CATALYSTS<br/>[FR] ADDITIONS ASYMETRIQUES DE MICHAEL ET D'ALDOL UTILISANT DES CATALYSEURS BIFONCTIONNELS A BASE DE CINCHONINE
  申请人：UNIV BRANDEIS

  公开号：WO2005121137A1

  公开（公告）日：2005-12-22

  One aspect of the present invention relates to quinine-based and quinidine-based catalysts. Another aspect of the invention relates to a method of preparing a derivatized quinine-based or quinidine-based catalyst comprising 1) reacting quinine or quinidine with 5 base and a compound that has a suitable leaving group, and 2) converting the ring methoxy group to a hydroxy group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone, comprising the step of: reacting a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral 10 ketone with a nucleophile in the presence of a catalyst; thereby producing a chiral, non racemic compound; wherein said catalyst is a derivatized quinine or quinidine. Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of reacting racemic chiral alkene with a nucleophile in the presence of a derivatized quinine or quinidine.

  本发明的一个方面涉及基于奎宁和奎宁的催化剂。发明的另一个方面涉及一种制备衍生奎宁或奎宁催化剂的方法，包括1）将奎宁或奎宁与5碱和具有适当离去基团的化合物反应，以及2）将环甲氧基转化为羟基。本发明的另一个方面涉及一种从前手性电子亏缺烯烃或偶氮化合物或前手性醛或前手性酮制备手性、非拉克米化合物的方法，包括以下步骤：在催化剂存在下，将前手性电子亏缺烯烃或偶氮化合物或前手性醛或前手性酮与亲核试剂反应；从而产生手性、非拉克米化合物；其中所述催化剂是衍生奎宁或奎宁。本发明的另一个方面涉及一种动力学分辨的方法，包括在衍生奎宁或奎宁存在下，将拉克米手性烯烃与亲核试剂反应的步骤。
• Organocatalyzed Solvent-Free Aza-Henry Reaction:  A Breakthrough in the One-Pot Synthesis of 1,2-Diamines
  作者：Luca Bernardi、Bianca F. Bonini、Elena Capitò、Gabriella Dessole、Mauro Comes-Franchini、Mariafrancesca Fochi、Alfredo Ricci

  DOI：10.1021/jo0488762

  日期：2004.11.1

  A nitrogen-containing superbase such as TMG was found to be an effective catalyst for the reaction between N-diphenylphosphinoyl imines and nitroalkanes. Exploiting a protocol that avoids the use of any solvent also during workup procedure, we synthesized a series of β-nitroamines in excellent yields and high diastereomeric ratios. These results, combined with the capability of the indium in conjunction

  发现含氮的超碱例如TMG是N-二苯基膦酰基亚胺与硝基烷烃之间反应的有效催化剂。利用在后处理过程中也避免使用任何溶剂的方案，我们合成了一系列β-硝基胺，具有优异的收率和高的非对映体比率。这些结果，结合铟与锌作为化学计量还原剂的能力，可在温和的反应条件下在水介质中还原硝基，使我们设计出了三步一锅合成一系列在各个步骤中使用环保程序生产1,2-二胺。
• Electrochemically Induced Aza-Henry Reaction: A New, Mild, and Clean Synthesis of α-Nitroamines
  作者：Leucio Rossi、Achille Inesi、Gabriele Bianchi、Marta Feroci

  DOI：10.1055/s-2007-986643

  日期：2007.10

  The addition reaction of nitro compounds to azomethine functions, known as the aza-Henry (or nitro-Mannich) reaction was performed electrochemically under solvent and supporting electrolyte-free conditions. Reaction yields are very good and the method is very clean, avoiding the use of any classical solvent or catalyst.

  硝基化合物与偶氮甲碱官能团的加成反应，称为氮杂亨利（或硝基曼尼希）反应，是在无溶剂和支持电解质的条件下以电化学方式进行的。反应产率非常好，方法非常干净，避免使用任何经典溶剂或催化剂。