P,P,P-triphenyl-N-phenylsulfonylphosphine imide | 1056-25-3

• 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: P,P,P-triphenyl-N-phenylsulfonylphosphine imide
• 英文别名: N-(triphenyl-λ5-phosphaneylidene)benzenesulfonamide；N-Triphenylphosphoranyliden-benzolsulfonamid；Benzenesulfonamide, N-(triphenylphosphoranylidene)-；N-(triphenyl-λ5-phosphanylidene)benzenesulfonamide
• CAS: 1056-25-3
• 化学式: C₂₄H₂₀NO₂PS
• 分子量: 417.468
• InChiKey: MNSLPYMSWMILHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2935009090

反应信息

• 作为产物：
  描述：

  N,N-bis(trimethylsilyl)benzenesulfonamide 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 P,P,P-triphenyl-N-phenylsulfonylphosphine imide
  参考文献：
  名称：

  Bis[phenylsulphonylimino]iodoarenes: A New Type of Pentavalent Iodine Compound

  摘要：

  DOI：

  10.1055/s-1983-30375

文献信息

• Copper-catalyzed imination of sulfoxides and sulfides
  作者：Yuanyuan Liu、Hanying Wang、Xianjin Yang

  DOI：10.1016/j.tet.2019.07.020

  日期：2019.8

  and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene

  磺胺嘧啶和亚磺胺在有机化学家中引起了相当大的兴趣。在这项研究中，研究了使用各种N-氟苯磺酰胺的Cu（II）催化的亚砜和硫化物的亚胺化。通过使用几种取代的硫化物和亚砜来证明反应的范围。还检查了制备NH-磺胺嘧啶的流动策略。通过三苯膦截留腈中间体，我们发现该反应是通过金属-氮化物中间体机理进行的。
• Asymmetric α-substitution versus aza Diels–Alder reaction of electron deficient N-sulfonyl imines
  作者：Paul E. Morgan、Ray McCague、Andrew Whiting

  DOI：10.1039/a909116e

  日期：——

  Several N-arylsulfonylglycine esters have been brominated under photolytic conditions to provide the corresponding α-bromoglycine. These bromo esters can be treated with a range of bases to generate N-sulfonyl imino esters in situ; attempts to isolate the imines in a pure state were universally unsuccessful. Once generated, the imines can be trapped with cyclopentadiene to provide the corresponding aza Diels–Alder adducts in varying yields, depending upon the base used. In addition, if organometallic bases were employed (alkyllithiums and alkylaluminium reagents), not only were aza Diels–Alder adducts formed, but addition to the imine was also observed. In the case of organoaluminium reagents, imine addition was the major product. This process could be transformed into a stoichiometric asymmetric version, by generating a chiral aluminium reagent in situ to form a trialkyl (or trialkoxy) aluminium reagent, which when reacted with an N-sulfonyl bromoglycinate resulted in 19 to 62% enantiomeric excess of the corresponding substituted glycinate product.

  在光解条件下，几种 N-芳磺酰甘氨酸酯被溴化，生成相应的 δ-溴甘氨酸。这些溴化酯可以用一系列碱处理，在原位生成 N-磺酰亚胺酯；试图分离出纯净状态的亚胺的尝试普遍不成功。亚胺一旦生成，就可以与环戊二烯反应，生成相应的氮杂 DielsâAlder 加合物，根据所用碱的不同，产率也不同。此外，如果使用有机金属碱（烷基锂和烷基铝试剂），不仅可以生成氮杂 DielsâAlder 加合物，还可以观察到亚胺的加成反应。在有机铝试剂中，亚胺加成是主要产物。通过在原位生成手性铝试剂，形成三烷基（或三烷氧基）铝试剂，该试剂与 N-磺酰基溴甘氨酸反应后，相应的取代甘氨酸产物的对映体过量率为 19% 至 62%，从而将这一过程转化为化学计量不对称版本。
• Hypervalent Iodine in Synthesis XXXI: Formation of Phosphinimines and Arsinimines by Nitrene Route or Non-Nitrene Route
  作者：Wei Ou、Zhi-Gang Wang、Zhen-Chu Chen

  DOI：10.1080/00397919908086232

  日期：1999.7

  N-suIfonyltriphenylphosphinimines and N-sulfonyltriphenylarsinimines are prepared by the reaction of triphenylphosphine or triphenylarsine under nitrene-producing conditions with I-N ylide (PhI=NSO2R). Triphenylarsinimines can also be generated by a non-nitrene route from triphenylarsine, iodobenzene diacetate, and sulfonamides via triphenylarsine diacetale, Ph3As(OAc)2.

  摘要 N-磺酰基三苯基膦亚胺和N-磺酰基三苯基胂亚胺是由三苯基膦或三苯基胂在生成氮烯的条件下与IN ylide (PhI=NSO2R)反应制备的。三苯基胂亚胺也可以通过三苯基胂、碘苯二乙酸酯和磺酰胺通过三苯基胂二乙酰、Ph3As(OAc)2通过非硝烯途径生成。
• Synthesis of N-sulfonylamidines via three-component reaction of proline, aldehydes, and sulfonyl azides under metal-free conditions
  作者：Fattaneh Mohammadpour、Arash Ghaderi

  DOI：10.1007/s00706-022-02914-y

  日期：2022.6

  Synthesis of N-sulfonylamidines was performed by three-component coupling reaction of proline, aldehydes, and sulfonyl azides under mild conditions. In this reaction, using acetophenone as a representative ketone instead of aldehydes gave the desired product albeit in low yield. During our mechanistic studies, we trapped the nitrene as the key intermediate using PPh3. This simple and practical approach

  N-磺酰脒的合成通过脯氨酸、醛和磺酰叠氮化物的三组分偶联反应在温和条件下进行。在该反应中，使用苯乙酮作为代表性酮代替醛得到所需产物，尽管收率低。在我们的机理研究中，我们使用 PPh 3捕获了作为关键中间体的氮烯。这种简单实用的方法可用于合成具有N-磺酰脒部分的生物活性分子。 图形概要
• Synthesis of N-acyl-, N-sulfonyl-, and N-phosphinylphospha(PV)azenes by a redox-condensation reaction using amides, triphenylphosphine, and diethyl azodicarboxylate
  作者：Shmuel Bittner、Yonit Assaf、Penina Krief、Martin Pomerantz、Barbara T. Ziemnicka、Christina G. Smith

  DOI：10.1021/jo00210a027

  日期：1985.5