3-phenylpenta-1,2-dienyl diphenyl phosphine oxide | 1190882-60-0

• 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: 3-phenylpenta-1,2-dienyl diphenyl phosphine oxide
• CAS: 1190882-60-0
• 化学式: C₂₃H₂₁OP
• 分子量: 344.393
• InChiKey: ZZZBOTCNXSNYHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-phenylpenta-1,2-dienyl diphenyl phosphine oxide 在 水 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以70%的产率得到2-fluoro-3-hydroxy-3-phenyl-1(E)-pentenyl diphenyl phosphine oxide
  参考文献：
  名称：

  Studies on highly regio- and stereoselective fluorohydroxylation reaction of 3-aryl-1,2-allenyl phosphine oxides with Selectfluor

  摘要：

  The fluorohydroxylation of allenyl phosphine oxides with Selectfluor in commercial MeCN without prior treatment or a mixed solvent of anhydrous MeCN (refluxed over CaH2 and distilled before use) and 7.0 equiv of H2O or MeNO2/H2O=10/1 afforded 2-fluoro-3-hydroxy-1(E)-alkenyl diphenyl phosphine oxides in moderate yields with very high regio- and stereoselectivities. The E-stereoselectivity is believed to be controlled by the phosphine oxide functionality. In the reaction of 3-(4-methoxyphenyl)-1,2-propadienyl diphenyl phosphine oxide, further fluorination on the electron-rich phenyl ring was also observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.009
• 作为产物：
  描述：

  3-phenyl-1-pentyn-3-ol 、 二苯基氯化膦 在 吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以55%的产率得到3-phenylpenta-1,2-dienyl diphenyl phosphine oxide
  参考文献：
  名称：

  Studies on highly regio- and stereoselective fluorohydroxylation reaction of 3-aryl-1,2-allenyl phosphine oxides with Selectfluor

  摘要：

  The fluorohydroxylation of allenyl phosphine oxides with Selectfluor in commercial MeCN without prior treatment or a mixed solvent of anhydrous MeCN (refluxed over CaH2 and distilled before use) and 7.0 equiv of H2O or MeNO2/H2O=10/1 afforded 2-fluoro-3-hydroxy-1(E)-alkenyl diphenyl phosphine oxides in moderate yields with very high regio- and stereoselectivities. The E-stereoselectivity is believed to be controlled by the phosphine oxide functionality. In the reaction of 3-(4-methoxyphenyl)-1,2-propadienyl diphenyl phosphine oxide, further fluorination on the electron-rich phenyl ring was also observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.009