(E)-N-diphenylphosphoryl-1-(3-nitrophenyl)methanimine | 1023287-82-2

• 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: (E)-N-diphenylphosphoryl-1-(3-nitrophenyl)methanimine
• CAS: 1023287-82-2
• 化学式: C₁₉H₁₅N₂O₃P
• 分子量: 350.313
• InChiKey: ZBEWEASTQNQDHY-HMMYKYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-丁二烯酸乙酯 、 (E)-N-diphenylphosphoryl-1-(3-nitrophenyl)methanimine 在 chiral bifunctional thiourea catalyst 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 48.42h， 生成 、 ethyl (2S)-1-(diphenylphosphoryl)-2-(3-nitrophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions

  摘要：

  A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.

  DOI：

  10.1021/ja801344w

文献信息

• Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions
  作者：Yuan-Qing Fang、Eric N. Jacobsen

  DOI：10.1021/ja801344w

  日期：2008.4.1

  A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.