2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one | 1341235-02-6

• 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: 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one
• 英文别名: 2-(5-Methyl-2-phenyl-2h-1,2,3-diazaphosphol-4-yl)-4h-benzo[d]-1,3,2-dioxaphosphorin-4-one；2-(5-methyl-2-phenyldiazaphosphol-4-yl)-1,3,2-benzodioxaphosphinin-4-one
• CAS: 1341235-02-6
• 化学式: C₁₆H₁₂N₂O₃P₂
• 分子量: 342.23
• InChiKey: BKMKEBFTAIQAFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-二叔丁基环己-3,5-二烯-1,2-二酮 、 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到
  参考文献：
  名称：

  Features of Reaction of 2-(5-Methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one with 1,2-Dicarbonyl Compounds

  摘要：

  2-(5-Methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one reacts with perfluorodiacetyl, 3,6-di(tert-butyl)-1,2-benzoquinone and phenanthrenequinone only with the participation of a three-coordinated phosphorus atom to form spirophosphoranes containing acyclic 5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl substituent, whereas the interaction with tetrachloro-1,2-benzoquinone proceeds via expanding the six-membered heterocycle to the nine-membered one to form 2-(2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-2,9-dioxo-4,5,6,7-tetrachlorodibenzo[d,h]-1,3,8-trioxaphosphonine.

  DOI：

  10.1134/s107036321803009x
• 作为产物：
  描述：

  4-(dichlorophosphino)-5-methyl-2-phenyl-2H-1,2,3-diazaphosphole 、 三甲基甲硅烷醇三硅甲烷氧基水杨酯 以 二氯甲烷 为溶剂， 以93%的产率得到2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one
  参考文献：
  名称：

  2-(5-methyl-2-phenyl-2h-1,2,3-diazaphosphol-4-yl)-4h-benzo[e]-1,3,2-dioxaphosphinin-4-one 与活性羰基的相互作用化合物。含二配位和四配位磷的双杂环系统的合成

  摘要：

  图形摘要摘要 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphinin-4-one 的相互作用与中草酸和三氟丙酮酸乙酯和二乙酯、六氟丙酮和氯醛在 P(III) 原子的独家参与下进行，并允许获得 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4 -yl)- 1,4,2- 和 1,3,2- 二氧磷以及二氯乙烯基膦酸酯的衍生物，在氯醛的情况下是 Perkow 反应的产物。

  DOI：

  10.1080/10426507.2017.1390459

文献信息

• Reaction of ethyl trifluoropyruvate with 2-(5-Methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[d]-1,3,2-dioxaphosphorin-4-one. Effect of exocyclic substituent on chemoselectivity
  作者：V. F. Mironov、G. A. Ivkova、L. M. Abdrakhmanova、I. V. Konovalova

  DOI：10.1134/s1070363211110272

  日期：2011.11

  only. The trifluoropyruvate ester contains a prochiral carbonyl group, which is the source of the second chiral center (C), causing the formation of two diastereomers (55:45) of the reaction product II, whose structure was established by the NMR and mass spectrometry. The H, С–H}, Р–H} NMR spectra of the compound II purified from the volatile impurities contain a double set of signals that can not

  Benzo[d]-1,3,2-dioxaphosphorin-4-ones（水杨酸的 P-磷酸化环状衍生物），含有亲核磷原子和亲电子环内羰基，具有特定的反应性。它们很容易通过具有多个键的活化系统的作用将环增加到七元环[1-6]。苯并[d]-1,3,2-dioxaphosphorin-4-one 的磷原子是一种环外取代基，含有 P 原子的 λσ-二氮杂磷片段可以改变与活化不饱和系统相互作用的方向，例如羰基化合物。事实上，似乎化合物 I 中的弱受体和庞大的二氮杂磷部分导致与三氟丙酮酸乙酯的反应方向发生变化。与 benzo[d]1,3,2-dioxaphosphorin-4-one [7] 的普通衍生物相比，这里主要 (>90%) 形成 (Р–С → Р–ОС)-重组产物，即仅涉及二氧杂膦片段的 1,3,2-二氧杂膦衍生物 II。三氟丙酮酸酯含有一个前手性羰基，它是第二个手性中心 (C) 的来源，导致反应产物
• Formation of the P–C and C–C bonds in the Reaction of 2-(5-Methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one with Dimethyl Acetylenedicarboxylate under Mild Conditions
  作者：V. F. Mironov、G. A. Ivkova、R. Z. Musin、L. M. Abdrakhmanova

  DOI：10.1134/s1070363218030350

  日期：2018.3

  e]-1,3,2-dioxaphosphorin-4-one reacts under mild conditions with dimethyl acetylenedicarboxylate with the participation by only threecoordinated phosphorus atom and the formation of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-3,4-dimethoxycarbonylbenzo[f]-1,2-oxaphosphepine-2,5-dione. During the process, simultaneous formation of the P–C and C–C bonds takes place.

  2-（5-甲基-2-苯基-2 H -1,2,3-二氮杂磷-4-基）-4 H-苯并[ e ] -1,3,2-二氧杂磷烷基-4-酮在温和条件下反应与乙炔二羧酸二甲酯一起仅由三个配位的磷原子参与，并形成2-（5-甲基-2-苯基-2 H -1,2,3-二氮杂磷-4-基）-3,4-二甲氧基羰基苯并[f] -1,2-氧杂磷平-2,5-二酮。在此过程中，同时形成了P–C和C–C键。
• 2-(5-Methyl-2-Phenyl-2<i>H</i>-1,2,3-Dizaphosphol-4-YL)-4<i>H</i>-Benzo[<i>D</i>]-1,3,2-Dioxaphosphorin-4-One in the Synthesis of Bis-Heterocyclic 1,4,2-Oxazaphosphepine Derivatives
  作者：Vladimir F. Mironov、Gulnara A. Ivkova、Andrey V. Bogdanov、Liliya M. Burnaeva、Petro Onys’ko、Yulia Rassukanaya

  DOI：10.1080/10426507.2014.985822

  日期：2015.6.3

  The reaction of 2-(5-methyl-2-phenyl-2H-1,2,3-dizaphosphol-4-yl)-4H-benzo[d]-1,3,2-dioxaphosphorin-4-one with arylimines leads to the formation of seven-membered heterocycles, 3-aryl-2-(5-methyl-2-phenyl-2H-1,2,3-dizaphosphol-4-yl)benzo[f]-1,4,2-oxaza-phosphepin-5-ones with moderate stereoselectivity. 1,2,3-Diazaphospholic moiety does not take part in the process and fulfills the role of sterically hindered substituent.
• Special features of reaction of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[d]-1,3,2-dioxaphosphorin-4-one with diethyl mesoxalate
  作者：V. F. Mironov、G. A. Ivkova、L. M. Abdrakhmanova、L. M. Burnaeva、R. Z. Musin、S. V. Kharlamov、I. V. Konovalova

  DOI：10.1134/s1070428012020261

  日期：2012.2