diethyl (1,1-difluoro-3-phenylprop-2-yn-1-yl)phosphonate

• 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 (1,1-difluoro-3-phenylprop-2-yn-1-yl)phosphonate
• 英文别名: diethyl [1,1-difluoro-3-phenyl-2-propyn-1-yl]phosphonate；diethyl 1,1-difluoro-3-phenylprop-2-ynylphosphonate；diethyl 1,1-difluoro-3-phenyl-2-propynephosphonate；(3-Diethoxyphosphoryl-3,3-difluoroprop-1-ynyl)benzene
• 化学式: C₁₃H₁₅F₂O₃P
• 分子量: 288.231
• InChiKey: XIPNORFFZUMXMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  lithium phenylacetylide 在 溴 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 diethyl (1,1-difluoro-3-phenylprop-2-yn-1-yl)phosphonate
  参考文献：
  名称：

  An alternative route for the preparation of α,α-difluoropropargylphosphonates

  摘要：

  The organometallic reagent, (EtO)(2)P(O)CF2ZnBr, reacts with 1-bromoalkynes in the presence of CuBr to give good yields (50-61%) of alpha,alpha-difluoropropargylphosphonates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01354-x

文献信息

• Copper-Mediated Introduction of the CF₂ PO(OEt)₂ Motif: Scope and Limitations
  作者：Maria V. Ivanova、Alexandre Bayle、Tatiana Besset、Xavier Pannecoucke、Thomas Poisson

  DOI：10.1002/chem.201703542

  日期：2017.12.6

  can be functionalised. The procedure allows the conversion of aryl diazonium salts, as well as aryl, heteroaryl, vinyl and alkynyl iodonium salts, into the corresponding fluorinated molecules at room temperature. Mechanistic studies were performed to gain a better understanding of the reaction pathway. Under similar conditions, vinyl and aryl iodides, allyl halides, and benzyl bromides were also functionalised

  在本文中，报告了访问包含CF 2 PO（OEt）2的分子的一般程序。试剂CuCF 2 PO（OEt）2可以通过简单的协议访问，并且可以对多种底物进行功能化。该方法允许在室温下将芳基重氮盐以及芳基，杂芳基，乙烯基和炔基碘鎓盐转化为相应的氟化分子。进行了机理研究，以更好地了解反应途径。在相似的条件下，乙烯基和芳基碘化物，烯丙基卤化物和苄基溴化物也被官能化，并且研究了反应的范围和局限性。最后，该程序扩展到二硫化物，以提供新的SCF 2通道含PO（OEt）2的分子。
• Copper-Mediated Oxidative Cross-Coupling Reaction of Terminal Alkynes with α-Silyldifluoromethylphosphonates: An Efficient Method for α,α-Difluoropropargylphosphonates
  作者：Xueliang Jiang、Lingling Chu、Feng-Ling Qing

  DOI：10.1021/ol301113v

  日期：2012.6.1

  A copper-mediated oxidative cross-coupling reaction of terminal alkynes with readily available α-silyldifluoromethylphosphonates under mild conditions has been developed. This method allows for an efficient synthesis of a series of synthetically useful α,α-difluoropropargylphosphonates with excellent functional group compatibility.

  已经开发了在温和条件下，末端炔烃与容易获得的α-甲硅烷基二氟甲基膦酸酯的铜介导的氧化交叉偶联反应。该方法允许有效合成具有优异的官能团相容性的一系列合成上有用的α，α-二氟炔丙基膦酸酯。
• Synthesis of fluoroalkylated alkynes <i>via</i> visible-light photocatalysis
  作者：Naila Iqbal、Naeem Iqbal、Sung Su Han、Eun Jin Cho

  DOI：10.1039/c8ob02486c

  日期：——

  Fluoroalkylated alkynes, which are versatile building blocks for the synthesis of various biologically active organofluorine compounds, were synthesized from easily available alkynyl halides and fluoroalkyl halides by visible-light photocatalysis. Addition of fluoroalkyl radicals to alkynes and subsequent dehalogenation selectively yielded fluoroalkylated alkynes.

  氟烷基化炔烃是用于合成各种生物活性有机氟化合物的通用构建基块，是通过可见光光催化由易于获得的炔基卤化物和氟代烷基卤化物合成的。将氟烷基自由基加至炔烃并随后脱卤选择性地产生氟烷基化的炔烃。
• Copper‐Mediated Formation of Aryl, Heteroaryl, Vinyl and Alkynyl Difluoromethylphosphonates: A General Approach to Fluorinated Phosphate Mimics
  作者：Maria V. Ivanova、Alexandre Bayle、Tatiana Besset、Thomas Poisson、Xavier Pannecoucke

  DOI：10.1002/anie.201507130

  日期：2015.11.2

  A general and efficient access to aryl, heteroaryl, vinyl and alkynyl difluoromethylphosphonates is described. The developed methodology using TMSCF2PO(OEt)2, iodonium salts and a copper salt provided a straightforward manifold to reach these highly relevant products. The reaction proved to be highly functional group tolerant and proceeded under mild conditions, giving the corresponding products in

  描述了一般和有效地获得芳基，杂芳基，乙烯基和炔基二氟甲基膦酸酯的方法。使用TMSCF 2 PO（OEt）2，碘鎓盐和铜盐开发的方法为获得这些高度相关的产品提供了直接途径。该反应被证明是高度官能团耐受的，并且在温和的条件下进行，从而给出相应的产物，收率良好至优异。该方法代表了这一重要类别的氟化支架的第一个通用合成路线，众所周知，该支架为体内稳定的磷酸盐替代物。
• An expedient synthesis of (α,α-difluoroprop-2-ynyl)phosphonate esters
  作者：Farid Benayoud、Gerald B. Hammond

  DOI：10.1039/cc9960001447

  日期：——

  Pfitzner-Moffatt oxidation of diethyl alpha-hydroxyalkynephosphonate 4, prepared by nucleophilic attack of diethyl phosphite on the corresponding aldehyde, followed by DAST fluorination of the resulting alpha-ketophosphonate 8, results in the smooth formation of alpha,alpha-difluoroalkynephosphonate 7.