N-phenylacetyltriphenylphosphinimine | 153595-68-7

• 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-phenylacetyltriphenylphosphinimine
• 英文别名: triphenylphosphine N-phenylacetylimide；2-phenyl-N-(triphenyl-l5-phosphaneylidene)acetamide；2-phenyl-N-(triphenyl-λ⁵-phosphaneylidene)acetamide；2-phenyl-N-(triphenyl-λ⁵-phosphanylidene)acetamide；2-phenyl-N-(triphenyl-lambda5-phosphanylidene)acetamide；2-phenyl-N-(triphenyl-λ5-phosphanylidene)acetamide
• CAS: 153595-68-7
• 化学式: C₂₆H₂₂NOP
• 分子量: 395.441
• InChiKey: MAOFGTNKHNOPLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-phenylacetyltriphenylphosphinimine 在 Dowex (H form) 、 水 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 53.0h， 生成 5'-(N-phenylacetyl)amino-5'-deoxy-4,5-didehydrouridine
  参考文献：
  名称：

  Gentle, Caragh A.; Bugg, Timothy D. H., Journal of the Chemical Society. Perkin transactions I, 1999, # 10, p. 1279 - 1285

  摘要：

  DOI：
• 作为产物：
  描述：

  N-羟基-2-苯基-乙酰胺 在 三乙胺 、 iron(II) chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 22.0h， 生成 N-phenylacetyltriphenylphosphinimine
  参考文献：
  名称：

  铁(II)催化膦与N-酰氧基酰胺的亚胺化构建N-酰基亚氨基正膦

  摘要：

  使用 FeCl 2作为廉价且容易获得的催化剂，描述了膦与 N-酰氧基酰胺的简便亚胺化反应，提供了具有高官能团耐受性的合成有用的N-酰基亚氨基正膦。该转化在室温下的空气气氛下很容易进行，并且可以在催化剂负载量为 1 mol% 的情况下放大至克级。产物中的亚氨基正膦基部分被进一步用作在 Rh(III) 催化下可控邻位C(sp 2 )-H 键酰胺化的有效导向基团。

  DOI：

  10.1021/acs.orglett.2c01238

文献信息

• Photoredox Catalytic Phosphine-Mediated Deoxygenation of Hydroxylamines Enables the Construction of <i>N</i>-Acyliminophosphoranes
  作者：Wencheng Han、Junqi Su、Jia-Nan Mo、Jiannan Zhao

  DOI：10.1021/acs.orglett.2c02226

  日期：2022.9.2

  phosphoranyl radicals has received increasing attention in recent years. Here, we report the generation of amidyl radicals through photocatalytic deoxygenation of hydroxylamines with triphenylphosphine. This methodology offers a novel and convenient route to a diverse range of N-acyliminophosphoranes in moderate to good yields under visible-light photoredox conditions. Fluorescence quenching experiments

  磷酰基自由基的化学近年来受到越来越多的关注。在这里，我们报告了通过羟胺与三苯膦的光催化脱氧产生酰胺基自由基。该方法为在可见光光氧化还原条件下以中等至高产率制备多种N-酰基亚氨基正膦提供了一种新颖且便捷的途径。荧光猝灭实验表明有机光催化剂 (4CzIPN) 的激发态被 Cu(II) 盐氧化猝灭。
• Copper(I)‐Catalyzed Decarboxylative <i>N</i>‐Phosphorylation: Modular Preparation of <i>N</i>‐Acyl Iminophosphoranes Using Dioxazolones and Phosphines
  作者：Jinhwan Park、Anattil Unnikrishnan Krishnapriya、Yeongmi Park、Minsuk Kim、Tyler W. Reidl、Rositha Kuniyil、Jongwoo Son

  DOI：10.1002/adsc.202300693

  日期：2023.12.19

  Dioxazolones and phosphines have been used to access N-acyl iminophosphoranes in copper(I) catalysis under simple thermal conditions. The synthetic utility of this protocol is demonstrated by a broad range of substrates with an excellent atom-economy. The optimization process showed that copper demonstrated as catalytic amount toward the targeted transformation. Functionalization studies of N-acyl

  二恶唑酮和膦已被用于在简单的热条件下在铜(I)催化中获得N-酰基亚氨基正膦。该协议的合成实用性通过具有出色原子经济性的广泛底物得到证明。优化过程表明铜对目标转化具有催化作用。还进行了N-酰基亚氨基正膦的官能化研究。我们的反应方案与含有生物活性基序的N-酰基亚氨基正膦类似物的示例兼容。
• Generation of Nitrene by the Photolysis of <i>N</i>-Substituted Iminodibenzothiophene
  作者：Hiroyuki Morita、Atsushi Tatami、Tetsuo Maeda、Byung Ju Kim、Wataru Kawashima、Toshiaki Yoshimura、Hitoshi Abe、Takeshi Akasaka

  DOI：10.1021/jo800604t

  日期：2008.9.19

  To evaluate the ability of dibenzothiophene N-substituted sulfilimines as photochemical nitrene sources, their photolyses in the presence of several trapping reagents, such as sulfides, olefins, and phosphorus compounds, were performed. In the reactions, the corresponding imino-transfer compounds, namely sulfilimines, aziridines, and iminophosphoranes, were formed in good yields, indicating dibenzothiophene N-tosyl and N-acylsulfilimines have a potent nature as nitrogen sources.
• Froeyen, Paul, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 78, # 1-4, p. 161 - 172
  作者：Froeyen, Paul

  DOI：——

  日期：——
• Regioselective Ortho Palladation of Stabilized Iminophosphoranes in Exo Positions: Scope, Limitations, and Mechanistic Insights
  作者：David Aguilar、Raquel Bielsa、María Contel、Agustí Lledós、Rafael Navarro、Tatiana Soler、Esteban P. Urriolabeitia

  DOI：10.1021/om701174v

  日期：2008.7.1

  The reactivity of the stabilized iminophosphoranes R3P = NC(O)Ph (R = p-tolyl, m-tolyl), Ph3P = NC(O)CH2Ph, and Ph2P(CH2)(n)PPh2 = NC(O)Ph (n = 1, 2) toward Pd(OAc)(2) has been examined. These substrates undergo palladation at the ortho C(sp(2))-H bond of the benzamide ring, giving exo complexes with complete regioselectivity. The mechanism of this reaction has been studied using DFT calculations and the regioselectivity explained on a kinetic basis, since the activation barrier is lower for the exo pathway than for the endo. The origin of this lower energy for the exo barrier seems to reside mainly on the interaction energy between the metal center and the ligand at the transition state. On the other hand, the palladation of the related keto-stabilized systems Ph3P = NC(O)FG (FG = NC4H8, NC4H8O) gives selectively the endo isomers through C-H bond activation at the Ph ring of the PPh3 unit.