diethyl difluoro{4-[3-hydroxy-2-(hydroxymethyl)propyl]phenyl}methylphosphonate | 213127-72-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl difluoro{4-[3-hydroxy-2-(hydroxymethyl)propyl]phenyl}methylphosphonate
• 英文别名: 2-[[4-[Diethoxyphosphoryl(difluoro)methyl]phenyl]methyl]propane-1,3-diol
• CAS: 213127-72-1
• 化学式: C₁₅H₂₃F₂O₅P
• 分子量: 352.315
• InChiKey: INYXATRBDNFMMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl difluoro{4-[3-hydroxy-2-(hydroxymethyl)propyl]phenyl}methylphosphonate 在 palladium on activated charcoal jones reagent 、 Lipase PS 、 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 生成 (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)(difluoro)methyl]phenyl}propyl acetate
  参考文献：
  名称：

  Enzymatic desymmetrization of prochiral 2-benzyl-1,3-propanediol derivatives: A practical chemoenzymatic synthesis of novel phosphorylated tyrosine analogues

  摘要：

  (Phosphonomethyl)phenylalanine (Pmp) and (phosphonodifluoromethyl)phenylalanine (F(2)Pmp) as well as their beta-amino acid congeners were prepared as a protecting variant amenable to the peptide synthesis from readily available 2-benzyl-1,3-propandiols possessing either a diethylphosphonomethyl- or diethylphosphonodifluoromethyl functionality at the para-position via the lipase-catalyzed desymmetrization. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00586-9
• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 、 copper(I) bromide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 N,N-二甲基乙酰胺 为溶剂， 反应 5.5h， 生成 diethyl difluoro{4-[3-hydroxy-2-(hydroxymethyl)propyl]phenyl}methylphosphonate
  参考文献：
  名称：

  Enzymatic desymmetrization of prochiral 2-benzyl-1,3-propanediol derivatives: A practical chemoenzymatic synthesis of novel phosphorylated tyrosine analogues

  摘要：

  (Phosphonomethyl)phenylalanine (Pmp) and (phosphonodifluoromethyl)phenylalanine (F(2)Pmp) as well as their beta-amino acid congeners were prepared as a protecting variant amenable to the peptide synthesis from readily available 2-benzyl-1,3-propandiols possessing either a diethylphosphonomethyl- or diethylphosphonodifluoromethyl functionality at the para-position via the lipase-catalyzed desymmetrization. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00586-9

文献信息

• Enzymatic desymmetrization of prochiral 2-benzyl-1,3-propanediol derivatives: A practical chemoenzymatic synthesis of novel phosphorylated tyrosine analogues
  作者：Tsutomu Yokomatsu、Takayuki Minowa、Tetsuo Murano、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(98)00586-9

  日期：1998.8

  (Phosphonomethyl)phenylalanine (Pmp) and (phosphonodifluoromethyl)phenylalanine (F(2)Pmp) as well as their beta-amino acid congeners were prepared as a protecting variant amenable to the peptide synthesis from readily available 2-benzyl-1,3-propandiols possessing either a diethylphosphonomethyl- or diethylphosphonodifluoromethyl functionality at the para-position via the lipase-catalyzed desymmetrization. (C) 1998 Elsevier Science Ltd. All rights reserved.