[furan-2-yl(diphenyl)phosphonio](methoxycarbonyl) | 1448325-79-8

• 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: [furan-2-yl(diphenyl)phosphonio](methoxycarbonyl)
• CAS: 1448325-79-8
• 化学式: BF₄*C₂₅H₂₁IO₃P
• 分子量: 614.123
• InChiKey: PFASQELLOWPVDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  45.43
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-癸炔 、 [furan-2-yl(diphenyl)phosphonio](methoxycarbonyl) 以 二氯甲烷 为溶剂， 以10%的产率得到methyl 4-octyl-7,7-diphenyl-7λ⁵-phosphinino[2,3-b]furan-6-carboxylate
  参考文献：
  名称：

  Annelated P-containing heterocycles from aryl- and hetaryl-substituted phosphonium iodonium ylides with a methoxycarbonyl-group

  摘要：

  Hetaryl-substituted phosphonium iodonium ylides with a methoxycarbonyl group as acceptor proved to be highly reactive toward various alkynes in comparison with triphenyl-substituted analogue. We were able to isolate annelated P-containing heterocycles-lambda(5)-phosphininothiophenes, lambda(5)-phosphininofurans, lambda(5)-phosphinolines, and rare polyaryl-substituted phosphonium salts, which can be traced back to three different rotamers of an intermediate adduct of the alkyne with the cation generated from the mixed ylide by removal of iodobenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.066
• 作为产物：
  描述：

  (2-furyl)diphenylphosphine 在 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.0h， 生成 [furan-2-yl(diphenyl)phosphonio](methoxycarbonyl)
  参考文献：
  名称：

  Annelated P-containing heterocycles from aryl- and hetaryl-substituted phosphonium iodonium ylides with a methoxycarbonyl-group

  摘要：

  Hetaryl-substituted phosphonium iodonium ylides with a methoxycarbonyl group as acceptor proved to be highly reactive toward various alkynes in comparison with triphenyl-substituted analogue. We were able to isolate annelated P-containing heterocycles-lambda(5)-phosphininothiophenes, lambda(5)-phosphininofurans, lambda(5)-phosphinolines, and rare polyaryl-substituted phosphonium salts, which can be traced back to three different rotamers of an intermediate adduct of the alkyne with the cation generated from the mixed ylide by removal of iodobenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.066

文献信息

• Furyl-Substituted Mixed Phosphonium-Iodonium Ylides in the Synthesis of Annelated P-Containing Heterocyclic Compounds
  作者：Elena D. Matveeva、Dmitrii S. Vinogradov、Tatyana A. Podrugina、Tatiana D. Nekipelova、Andrey V. Mironov、Rolf Gleiter、Nikolay S. Zefirov

  DOI：10.1002/ejoc.201500876

  日期：2015.11

  Photochemical reactions between stabilized furyl-substituted phosphonium–iodonium ylides and terminal acetylenes led to the formation of new P-containing heterocyclic compounds. For the heterocyclization of 2-furyl-substituted ylides, we observed an unprecedented electrophilic ipso attack onto the α position of the furan ring in a carbocationic intermediate, leading – via a spiro intermediate – to

  稳定的呋喃基取代的鏻-碘鎓叶立德与末端乙炔之间的光化学反应导致形成新的含磷杂环化合物。对于 2-呋喃基取代的叶立德的杂环化，我们观察到前所未有的亲电同向攻击碳阳离子中间体中呋喃环的 α 位置，通过螺中间体导致重排产物在呋喃环。