(difluoromethyl)phosphonic acid | 74963-39-6

• 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: (difluoromethyl)phosphonic acid
• 英文别名: DIFLUOROMETHYLPHOSPHONIC ACID
• CAS: 74963-39-6
• 化学式: CH₃F₂O₃P
• 分子量: 132.004
• InChiKey: NCEMUOYFYLEORV-UHFFFAOYSA-N

物化性质

• 沸点：
  287.7±45.0 °C(Predicted)
• 密度：
  1.748±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (difluoromethyl)phosphonic acid 在 吡啶 、 草酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 二氯磷(二氟)甲烷
  参考文献：
  名称：

  合成有用的膦酸二氯化物的温和制备：在合成环状膦酸二酯和二酰胺中的应用

  摘要：

  已经开发了一种非常温和的制备合成上有用的二氯化膦的方法，并将其用于合成2-烷基-2-氧代-1、3、2-二氧代膦酰基和1，3-二甲基-2-烷基-2-基。报导了oxo-1、3、2-二氮杂膦烷。

  DOI：

  10.1016/s0040-4039(00)89038-3
• 作为产物：
  描述：

  二氟甲基膦酸二乙酯 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (difluoromethyl)phosphonic acid
  参考文献：
  名称：

  Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases

  摘要：

  IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5'-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not assured, and usually is inefficient. In order to bypass cellular phosphorylation, a series of azole nucleoside 5'-MP mimics (P1Ms) based on ribavirin, EICAR and bredinin were synthesized and screened against human and C. albicans IMP dehydrogenises. P1Ms 8, 16, 25, 28 and 29 demonstrated substantial IMPDH inhibition with K-i values in low micromolar range.

  DOI：

  10.1081/ncn-120027838

文献信息

• A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids
  作者：Natalia V Pavlenko、Tatiana I Oos、Yurii L Yagupolskii、Igor I Gerus、Uwe Doeller、Lothar Willms

  DOI：10.3762/bjoc.10.66

  日期：——

  A series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids - analogues of proteinogenic and nonproteinogenic alpha-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine

  制备了一系列新型 (1-氨基烷基)(三氟甲基)-和-(二氟甲基) 次膦酸-蛋白质和非蛋白质α-氨基酸的类似物。合成方法基于（三氟甲基）次膦酸或（二氟甲基）次膦酸或其乙酯与具有 C=N 或活化的 C=C 双键的底物的亲核加成。由此制备了甘氨酸、苯基甘氨酸、丙氨酸、缬氨酸、脯氨酸、氨基丙二酸和天冬氨酸的类似物。还测试了（三氟甲基）次膦酸和二苄胺与醛的三组分一锅反应以制备标题化合物。
• Novel fluorophosphonate nucleotide derivatives
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0339161A1

  公开（公告）日：1989-11-02

  This invention relates to fluoromethylphosphonate derivatives of certain nucleosides, to methods for their preparation and to their use as antiviral and antitumoral agents.

  这项发明涉及某些核苷类化合物的氟甲基磷酸酯衍生物，涉及它们的制备方法以及它们作为抗病毒和抗肿瘤药物的用途。
• Etude d'un schema de synthese peptidique intramoleculaire a l'aide de derives du phosphore tetraedrique
  作者：M. Mulliez

  DOI：10.1016/s0040-4020(01)97957-8

  日期：——

  A new scheme of repetitive and controlled peptide synthesis offers two advantages compared to the usual methods of synthesis : two steps only are used for the prolongation of a peptide chain with an aminoacid residue and the risk of racemisation is minimized. The two postulated steps are verified particularly by the rearrangement, in an alkaline alcoholic medium, of phosphordiamides 1 incorporating

  与常规的合成方法相比，重复和受控的肽合成的新方案具有两个优点：仅两个步骤用于延长带有氨基酸残基的肽链，并且将外消旋化的风险降至最低。特别地，通过在碱性醇介质中重新排列掺入一个氨基酸残基的磷二酰胺1，导致形成肽衍生物6和8，证实了这两个假定的步骤。讨论了此方法的严重局限性。
• STOWELL, MICHAEL H. B.;UELAND, JOSEPH M.;MCCLARD, RONALD W., TETRAHEDRON LETT., 31,(1990) N3, C. 3261-3262
  作者：STOWELL, MICHAEL H. B.、UELAND, JOSEPH M.、MCCLARD, RONALD W.

  DOI：——

  日期：——
• Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases
  作者：Guangyi Wang、Kandasamy Sakthivel、Vasanthakumar Rajappan、Thomas W. Bruice、Kathleen Tucker、Patrick Fagan、Jennifer L. Brooks、Tiffany Hurd、Janet M. Leeds、P. Dan Cook

  DOI：10.1081/ncn-120027838

  日期：2004.1.1

  IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5'-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not assured, and usually is inefficient. In order to bypass cellular phosphorylation, a series of azole nucleoside 5'-MP mimics (P1Ms) based on ribavirin, EICAR and bredinin were synthesized and screened against human and C. albicans IMP dehydrogenises. P1Ms 8, 16, 25, 28 and 29 demonstrated substantial IMPDH inhibition with K-i values in low micromolar range.