Diisopropyl 2,6-difluorobenzoylphosphonate

• 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: Diisopropyl 2,6-difluorobenzoylphosphonate
• 英文别名: (2,6-Difluorophenyl)-di(propan-2-yloxy)phosphorylmethanone
• 化学式: C₁₃H₁₇F₂O₄P
• 分子量: 306.246
• InChiKey: ITOAERPLHSDPSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diisopropyl 2,6-difluorobenzoylphosphonate 在 (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 以96%的产率得到(S)-Diisopropyl (2,6-difluorophenyl)hydroxymethylphosphonate
  参考文献：
  名称：

  Asymmetric synthesis of chiral, nonracemic dialkyl-α-, β-, and γ-hydroxyalkylphosphonates via a catalyzed enantioselective catecholborane reduction

  摘要：

  A highly enantioselective synthesis of dialkyl alpha-hydroxyphosphonates achieved by a oxazaborolidine catalyzed reduction with catecholborane starting with m-ketophosphonates is described. Both alpha-aryl- and alpha-alkylketophosphonates were reduced using the (S)-enantiomer of the catalyst 4 leading also to the (S)-configuration in the products 2. The reaction gave good chemical yields and excellent enantiomeric excesses (up to >99 % ee).

  DOI：

  10.1016/0957-4166(95)00132-9
• 作为产物：
  描述：

  三异丙基亚磷酸酯 、 2,6-二氟苯甲酰氯 反应 2.0h， 以83%的产率得到Diisopropyl 2,6-difluorobenzoylphosphonate
  参考文献：
  名称：

  Meier, Chris; Laux, Wolfgang H. G.; Bats, Jan W., Liebigs Annalen, 1995, # 11, p. 1963 - 1980

  摘要：

  DOI：

文献信息

• Meier, Chris; Laux, Wolfgang H. G.; Bats, Jan W., Liebigs Annalen, 1995, # 11, p. 1963 - 1980
  作者：Meier, Chris、Laux, Wolfgang H. G.、Bats, Jan W.

  DOI：——

  日期：——
• Asymmetric synthesis of chiral, nonracemic dialkyl-α-, β-, and γ-hydroxyalkylphosphonates via a catalyzed enantioselective catecholborane reduction
  作者：Chris Meier、Wolfgang H.G. Laux

  DOI：10.1016/0957-4166(95)00132-9

  日期：1995.5

  A highly enantioselective synthesis of dialkyl alpha-hydroxyphosphonates achieved by a oxazaborolidine catalyzed reduction with catecholborane starting with m-ketophosphonates is described. Both alpha-aryl- and alpha-alkylketophosphonates were reduced using the (S)-enantiomer of the catalyst 4 leading also to the (S)-configuration in the products 2. The reaction gave good chemical yields and excellent enantiomeric excesses (up to >99 % ee).