tert-Butyl 2-fluoro-2-(triphenylphosphoranylidene)acetate | 201221-73-0

• 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: tert-Butyl 2-fluoro-2-(triphenylphosphoranylidene)acetate
• 英文别名: tert-butyl 2-fluoro-2-(triphenyl-λ5-phosphanylidene)acetate
• CAS: 201221-73-0
• 化学式: C₂₄H₂₄FO₂P
• 分子量: 394.426
• InChiKey: NCMHKLHCENNZNK-UHFFFAOYSA-N

物化性质

• 沸点：
  502.7±33.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  癸醛 、 tert-Butyl 2-fluoro-2-(triphenylphosphoranylidene)acetate 以 乙腈 为溶剂， 生成 (Z)-2-Fluoro-dodec-2-enoic acid tert-butyl ester
  参考文献：
  名称：

  A facile one-pot synthesis of α-fluoro-α,β-unsaturated esters from alkoxycarbonylmethyltriphenylphosphonium bromides

  摘要：

  A convenient one-pot synthesis of alpha-fluoro-alpha,beta-unsaturated esters from ethoxy- and tert-butoxycarbonylmethyltriphenylphosphoniurn bromide was developed. The fluorinated phosphoranes, generated in situ from alkoxycarbonylmethyltriphenylphosphoniurn bromides and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor(R)), undergo a Wittig reaction with aldehydes to yield alpha-fluoro-alpha,beta-misaturated esters with (Z)-selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.103
• 作为产物：
  描述：

  (叔丁氧基羰基亚甲基)三苯基磷烷 在 Selectfluor 、 sodium hydride 作用下， 以 乙腈 为溶剂， 生成 tert-Butyl 2-fluoro-2-(triphenylphosphoranylidene)acetate
  参考文献：
  名称：

  A facile one-pot synthesis of α-fluoro-α,β-unsaturated esters from alkoxycarbonylmethyltriphenylphosphonium bromides

  摘要：

  A convenient one-pot synthesis of alpha-fluoro-alpha,beta-unsaturated esters from ethoxy- and tert-butoxycarbonylmethyltriphenylphosphoniurn bromide was developed. The fluorinated phosphoranes, generated in situ from alkoxycarbonylmethyltriphenylphosphoniurn bromides and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor(R)), undergo a Wittig reaction with aldehydes to yield alpha-fluoro-alpha,beta-misaturated esters with (Z)-selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.103