3-phenyl-2,2-(bis(dicyclohexylamino)phosphino)(trimethylsilyl)-2H-aziridine | 167955-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 叠氮烷
• 英文名称: 3-phenyl-2,2-(bis(dicyclohexylamino)phosphino)(trimethylsilyl)-2H-aziridine
• 英文别名: N-cyclohexyl-N-[(dicyclohexylamino)-(3-phenyl-2-trimethylsilylazirin-2-yl)phosphanyl]cyclohexanamine
• CAS: 167955-65-9
• 化学式: C₃₅H₅₈N₃PSi
• 分子量: 579.925
• InChiKey: YLOBVEVZWVCXEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.31
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-2,2-(bis(dicyclohexylamino)phosphino)(trimethylsilyl)-2H-aziridine 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到2-[Bis(dicyclohexylamino)thioxophosphoranyl]-3-phenyl-2-trimethylsilyl-2H-azirine
  参考文献：
  名称：

  The Stable (Phosphino)(Silyl)Carbene As A Useful Building Block: Synthesis And Reactivity of 2-Phosphorus-Substituted 2H-Azirines

  摘要：

  Abstract[Bis(dicyclohexylamino)phosphino]trimethylsilylcarbene (1) reacts with benzonitrile leading to the corresponding 2‐phosphino‐2H‐azirine 3 in 85% yield. Treatment of 3 with trifluoro‐methanesulfonic acid, methyl trifluoro‐methanesulfonate, or elemental sulfur leads to the P‐hydrogeno‐2‐phosphonio‐,P‐methyl‐2‐phosphonio‐, or 2‐thioxo‐phosphoranyl‐2H‐azirine (4, 5, and 7) in 77, 87, and 91% yields, respectively. Irradiation of 3 gives rise to the 1,2λ5‐azaphosphete 8 (98% yield). Treatment of 3 with BF3·OEt2, BH3·SMe2, Lawesson's reagent, or methyl isothiocyanate gives heterocycles 9 (90% yield), 10 (76% yield), 12 (83% yield), or 13 (80% yield), while under the same experimental conditions, heterocycle 8 reacts with the same reagents to give 9 (82% yield), 11 (83% yield), 12 (86% yield), and 15 (56% yield), respectively. Thermolysis of the P‐hydrogeno‐2‐phosphonio‐2H‐azirine 4 at 55°C leads to the cationic, four‐membered heterocycle 17 (96% yield), while photolysis of the P‐methylazirine analogue 5 in the presence of dimethyl acetylenedicarboxylate affords pyrrole 19 (64% yield). Irradiation of the thiox‐ophosphoranyl azirine 7 gives the 1,3,5λ5‐thiazaphosphole 20 in 79% yield. The influence of the coordination state of phosphorus on the reactivity of 2‐phosphorus‐substituted 2H‐azirines is studied.

  DOI：

  10.1002/chem.19970031106
• 作为产物：
  描述：

  苯甲腈 、 [bis(dicyclohexylamino)phosphino](trimethylsilyl)carbene 以 甲苯 为溶剂， 以85%的产率得到3-phenyl-2,2-(bis(dicyclohexylamino)phosphino)(trimethylsilyl)-2H-aziridine
  参考文献：
  名称：

  4-π-Electron 4-Membered Phosphorus Heterocycles

  摘要：

  DOI：

  10.1080/10426509608545182

文献信息

• Alcaraz, Gilles; Wecker, Ulrich; Baceiredo, Antoine, Angewandte Chemie, 1995, vol. 107, # 11, p. 1358 - 1359
  作者：Alcaraz, Gilles、Wecker, Ulrich、Baceiredo, Antoine、Dahan, Francoise、Bertrand, Guy

  DOI：——

  日期：——
• 4-π-Electron 4-Membered Phosphorus Heterocycles
  作者：Regis Reau、Antoine Baceiredo、Guy Bertrand

  DOI：10.1080/10426509608545182

  日期：1996.1
• The Stable (Phosphino)(Silyl)Carbene As A Useful Building Block: Synthesis And Reactivity of 2-Phosphorus-Substituted 2H-Azirines
  作者：Valérie Piquet、Antoine Baceiredo、Heinz Gornitzka、Françoise Dahan、Guy Bertrand

  DOI：10.1002/chem.19970031106

  日期：1997.11

  Abstract[Bis(dicyclohexylamino)phosphino]trimethylsilylcarbene (1) reacts with benzonitrile leading to the corresponding 2‐phosphino‐2H‐azirine 3 in 85% yield. Treatment of 3 with trifluoro‐methanesulfonic acid, methyl trifluoro‐methanesulfonate, or elemental sulfur leads to the P‐hydrogeno‐2‐phosphonio‐,P‐methyl‐2‐phosphonio‐, or 2‐thioxo‐phosphoranyl‐2H‐azirine (4, 5, and 7) in 77, 87, and 91% yields, respectively. Irradiation of 3 gives rise to the 1,2λ5‐azaphosphete 8 (98% yield). Treatment of 3 with BF3·OEt2, BH3·SMe2, Lawesson's reagent, or methyl isothiocyanate gives heterocycles 9 (90% yield), 10 (76% yield), 12 (83% yield), or 13 (80% yield), while under the same experimental conditions, heterocycle 8 reacts with the same reagents to give 9 (82% yield), 11 (83% yield), 12 (86% yield), and 15 (56% yield), respectively. Thermolysis of the P‐hydrogeno‐2‐phosphonio‐2H‐azirine 4 at 55°C leads to the cationic, four‐membered heterocycle 17 (96% yield), while photolysis of the P‐methylazirine analogue 5 in the presence of dimethyl acetylenedicarboxylate affords pyrrole 19 (64% yield). Irradiation of the thiox‐ophosphoranyl azirine 7 gives the 1,3,5λ5‐thiazaphosphole 20 in 79% yield. The influence of the coordination state of phosphorus on the reactivity of 2‐phosphorus‐substituted 2H‐azirines is studied.