(E)-N-(2-methoxybenzylidene)-P,P-diphenylphosphinic amide | 252377-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-N-(2-methoxybenzylidene)-P,P-diphenylphosphinic amide
• 英文别名: N-(2-methoxybenzylidene)diphenylphosphinoylamide；(E)-N-diphenylphosphoryl-1-(2-methoxyphenyl)methanimine
• CAS: 252377-13-2
• 化学式: C₂₀H₁₈NO₂P
• 分子量: 335.342
• InChiKey: WIQOEAPTZVDICZ-LTGZKZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl(phenyl)silyllithium 、 (E)-N-(2-methoxybenzylidene)-P,P-diphenylphosphinic amide 在 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以90%的产率得到P,P-diphenyl-N-((dimethylphenylsilyl)(2-methoxyphenyl)methyl)phosphinic amide
  参考文献：
  名称：

  Stereoselective Synthesis of α-Silylamines by the Direct Addition of Silyl Anions to Activated Imines

  摘要：

  A highly efficient stereoselective synthesis of unusual alpha-silylamines via a direct silyl anion addition reaction is reported. This approach is convergent and avoids any problematic aza-Brook shifts of the anionic intermediates. The use of enantiopure tert-butanesulfinyl imines as the electrophiles affords exceedingly high levels of diastereocontrol for the newly formed stereogenic carbon.

  DOI：

  10.1021/ol050244u
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (E)-N-(2-methoxybenzylidene)-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  使用基于四氢噻吩的手性硫化物作为有机催化剂对二芳基氮丙啶的对映选择性合成。

  摘要：

  这项工作描述了使用（thiolan-2-yl）diarylmethanol苄基醚作为有机催化剂通过亚氨基Corey-Chaykovsky反应进行的苄基溴和亚胺的催化和不对称叠氮化（15例，95-98％ee）。通过快速有效的合成途径制备催化剂及其类似物，所述合成途径以双亲核取代和Shi环氧化为关键步骤。

  DOI：

  10.1039/c3cc47550f

文献信息

• 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%）。
• Synthesis of novel well-defined chain-end-functionalized polystyrenes with dendritic chiral ephedrine moieties and their applications as highly enantioselective diethylzinc addition to N-diphenylphosphinoyl arylimines
  作者：Ashraf A. El-Shehawy

  DOI：10.1016/j.tet.2007.08.093

  日期：2007.11

  A series of novel well-defined chain-end-functionalized polystyrenes having 2, 4, 8, and 16 chiral ephedrine moieties dendritically distributed at their hyperbranched chain-ends were quantitatively synthesized. Their well-defined architectures were fully confirmed by elemental analysis, FTIR, SEC as well as by 1H and 13C NMR spectroscopies. These polymers were precisely controlled in the molecular

  定量合成了一系列新颖的，定义明确的，具有2、4、8和16个手性麻黄碱部分在其超支化链端分布的手性麻油碱部分的链端官能化聚苯乙烯。通过元素分析，FTIR，SEC以及1 H和13 C NMR光谱学充分证实了它们的明确定义的体系结构。这些聚合物的分子量和分子量分布均得到精确控制，链端官能团也得到了明确定义。这些树状手性聚合物在二乙基锌向一系列N的对映选择性加成中充当高度对映选择性的手性配体-二苯基膦酰基芳基丙氨酸。其中，在链末端具有八个麻黄碱部分的手性树枝状聚合物以高至高收率提供了对映异构体富集的膦酰基酰胺，其对映选择性高达93％ee。所获得的对映选择性与使用N-苄基麻黄碱及其相应的共聚物作为手性配体所获得的对映选择性相当。
• (Thiolan-2-yl)diphenylmethyl benzyl ether/N,N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine
  作者：Shang-Hua Wang、Rong-Jie Chein

  DOI：10.1016/j.tet.2014.12.063

  日期：2016.5

  A dual catalyst system using THT-based chiral sulfide 2a and H-bond donor 10a was developed for the asymmetric imino Corey-Chaykovsky reaction. Under the optimum reaction conditions, cinnamyl bromide reacted with a wide scope of N-diphenylphosphinic aldimines, to give the major trans-aryl cinnamyl aziridines with up to 98% ee. The role of H-bond donor 10a was demonstrated empirically as well. (C) 2014 Elsevier Ltd. All rights reserved.
• Mattson, Anita E.; Scheidt, Karl A., Organic Letters, 2004, vol. 6, # 23, p. 4363 - 4366
  作者：Mattson, Anita E.、Scheidt, Karl A.

  DOI：——

  日期：——
• Novel chiral copper complexes of N,P-ferrocenyl ligands with central and planar chirality as efficient catalyst for asymmetric addition of diethylzinc to imines
  作者：Min-Can Wang、Lan-Tao Liu、Yuan-Zhao Hua、Jun-Song Zhang、Yan-Yan Shi、De-Kun Wang

  DOI：10.1016/j.tetasy.2005.06.005

  日期：2005.8

  A new type of chiral copper complexes of N,P-ferrocenyl ligands with central and planar chirality as efficient catalyst was applied to the enantioselective addition of diethylzinc to N-diphenylphosphinoylimines. The (R)- and (s)-enantiomers of the addition reaction were obtained for this transformation. In the presence of 6 mol % of bidentate ligand 1 and 12 mol % of Cu(OTf)(2), the asymmetric addition process affords N-diphenylphosphinoylamides in up to 97% ee and 95% yields. (c) 2005 Elsevier Ltd. All rights reserved.