diethyl 2,5-bis[(triphenyl-λ⁵-phosphanylidene)amino]thiophene-3,4-dicarboxylate | 147235-54-9

• 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: diethyl 2,5-bis[(triphenyl-λ⁵-phosphanylidene)amino]thiophene-3,4-dicarboxylate
• 英文别名: diethyl 2,5-bis(triphenylphosphoranylideneamino)thiophene-3,4-dicarboxylate；2,5-Bis(triphenylphosphinideneamino)-3,4-thiophenedicarboxylic acid diethyl ester；diethyl 2,5-bis[(triphenyl-λ5-phosphanylidene)amino]thiophene-3,4-dicarboxylate
• CAS: 147235-54-9
• 化学式: C₄₆H₄₀N₂O₄P₂S
• 分子量: 778.848
• InChiKey: QJGKFFLSLCQWIT-UHFFFAOYSA-N

物化性质

• 沸点：
  872.6±75.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 2,5-bis[(triphenyl-λ⁵-phosphanylidene)amino]thiophene-3,4-dicarboxylate 在 sodium ethanolate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Application of Bis(iminophosphorane) in Heterocyclic Synthesis:  New Entries to Symmetrically or Unsymmetrically Substituted Thieno[2,3-d:5,4-d‘]dipyrimidine-4,5(3H,6H)-diones

  摘要：

  The bis(carbodiimides) 4, obtained from bis-aza-Wittig reactions of bis(iminophosphorane) 3 with 2 equiv of aromatic isocyanates, were reacted with secondary amine to give symmetrically substituted 2,7-diaminothieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-dione 6 in the presence of a catalytic amount of EtO-Na+ Reactions of 4 with phenols or ROH in the presence of a catalytic amount of potassium carbonate or RO-Na+ gave symmetrically substituted 2,7-diaryl(alkyl)oxythieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 6 in satisfactory yields. However, iminophosphoranes 9 were obtained via reaction of bis(iminophosphorane) 3 with 1 equiv of aromatic isocyanate and subsequent reaction with an amine in the presence of a catalytic amount of EtO-Na+. Further reaction of iminophosphoranes 9 with aromatic isocyanates and various nucleophile generated unsymmetrically substituted thieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 12 in good yields.

  DOI：

  10.1021/jo048691v
• 作为产物：
  描述：

  2,5-二氨基-3,4-噻吩二羧酸二乙酯 、 三苯基膦 在 六氯乙烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以72%的产率得到diethyl 2,5-bis[(triphenyl-λ⁵-phosphanylidene)amino]thiophene-3,4-dicarboxylate
  参考文献：
  名称：

  A new, general approach for the synthesis of heteroannulated 3,1-oxazin-4-ones

  摘要：

  Beta-(N-Triphenylphosphoranyliden)-enamino esters afford the synthetically useful heteroannulated 3,1-oxazin-4-ones with aroyl chlorides in different solvents. The reaction proceeds in one step and in high yields and appears to be independent of the reactivity of the heterocyclic substrate.

  DOI：

  10.1016/s0040-4020(01)86261-x