(difluoromethyl)(octyl)phosphinic acid butyl ester

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: (difluoromethyl)(octyl)phosphinic acid butyl ester
• 英文别名: difluoromethyl-octyl-phosphinic acid butyl ester；1-[Butoxy(difluoromethyl)phosphoryl]octane
• 化学式: C₁₃H₂₇F₂O₂P
• 分子量: 284.327
• InChiKey: FPJVKYXRQARIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (difluoromethyl)(octyl)phosphinic acid butyl ester 、 碘甲烷 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 2.0h， 以85%的产率得到difluoromethyl-(1-methyl-octyl)-phosphinic acid butyl ester
  参考文献：
  名称：

  Synthesis and reactivity studies of α,α-difluoromethylphosphinates

  摘要：

  The preparation and reactivity of some a,alpha-difluorophosphinates are investigated. Alkylation of H-phosphinates with LiHMDS and ClCF2H gives the corresponding alpha,alpha-difluorophosphinates in good yield. Deprotonation of these reagents with alkyllithium or LDA is then studied. Subtle electronic effects translate into significant differences in the deprotonation/alkylation of the two 'Ciba-Geigy reagents' (EtO)(2)CRP(O)(OEt)H (R=H, Me). On the other hand, attempted methylation of difluoromethyl-octyl-phosphinic acid butyl ester resulted in the exclusive alkylation of the octyl chain. Finally, reaction with carbonyl compounds results in the formation of 1,1 -difluoro-2-phosphinoyl compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.036
• 作为产物：
  描述：

  氟里昂-22 、 butyl octyl-H-phosphinate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(difluoromethyl)(octyl)phosphinic acid butyl ester
  参考文献：
  名称：

  Alkylation of H-Phosphinate Esters under Basic Conditions

  摘要：

  An efficient and general procedure was developed for the direct alkylation of H-phosphinate esters with LHMDS at low temperature. The simplicity of the reaction allows the use of various H-phosphinate esters and takes place with a wide range of electrophiles. The approach can be employed to access some GABA analogues or precursors to GABA analogues. The isolated yields are moderate to good. This is the first report of an alkylation with a secondary iodide or a primary chloride.

  DOI：

  10.1021/jo062436o