diphenyl(2,2,2-trifluoroethyl)phosphine | 241495-60-3

• 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: diphenyl(2,2,2-trifluoroethyl)phosphine
• 英文别名: (2,2,2-Trifluoroethyl)diphenylphosphine；diphenyl(2,2,2-trifluoroethyl)phosphane
• CAS: 241495-60-3
• 化学式: C₁₄H₁₂F₃P
• 分子量: 268.218
• InChiKey: MJYYTCYDCIPJEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diphenyl(2,2,2-trifluoroethyl)phosphine 在 potassium tert-butylate 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 生成 (2,2-difluorovinyl)diphenylphosphine oxide
  参考文献：
  名称：

  A facile synthesis of 1-H-2,2-difluorovinylphosphorus compounds from 2,2,2-trifluoroethyl trifluoromethanesulfonate and substitutions of their vinylic fluorines

  摘要：

  2,2-Difluorovinylphosphine as well as its oxide and borane-complex are synthesized in high yields via the P-trifluoroethylation of lithium diphenylphosphide with 2,2,2-trifluoroethyl trifluoromethanesulfonate, followed by dehydrofluorination with potassium tert-butoxide. The reactions of 2,2-difluorovinylphosphine oxide and borane-complex with hydride, S- and N-nucleophiles proceed via an addition-elimination process to afford mono- or nonfluorovinylphosphorus compounds and carbamoylmethylphosphine oxides. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00037-8
• 作为产物：
  描述：

  2,2,2-三氟乙基三氟甲烷磺酸酯 、 二苯基膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以83%的产率得到diphenyl(2,2,2-trifluoroethyl)phosphine
  参考文献：
  名称：

  A facile synthesis of 1-H-2,2-difluorovinylphosphorus compounds from 2,2,2-trifluoroethyl trifluoromethanesulfonate and substitutions of their vinylic fluorines

  摘要：

  2,2-Difluorovinylphosphine as well as its oxide and borane-complex are synthesized in high yields via the P-trifluoroethylation of lithium diphenylphosphide with 2,2,2-trifluoroethyl trifluoromethanesulfonate, followed by dehydrofluorination with potassium tert-butoxide. The reactions of 2,2-difluorovinylphosphine oxide and borane-complex with hydride, S- and N-nucleophiles proceed via an addition-elimination process to afford mono- or nonfluorovinylphosphorus compounds and carbamoylmethylphosphine oxides. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00037-8

文献信息

• Photoredox-Catalyzed Selective α-Scission of PR₃–OH Radicals to Access Hydroalkylation of Alkenes
  作者：Zhen-Zhen Xie、Zi-Hao Liao、Yu Zheng、Chu-Ping Yuan、Jian-Ping Guan、Ming-Zhi Li、Ke-Yi Deng、Hao-Yue Xiang、Kai Chen、Hua Yang

  DOI：10.1021/acs.orglett.3c03632

  日期：2023.12.22

  Photoinduced generation of phosphoranyl radicals offers a versatile strategy to access a variety of synthetically valuable radicals. A long-standing challenge remains in the regulation of phosphoranyl radical to undergo α-scission pathway, although the β-scission mode has been intensively studied. We herein developed an unprecedented protocol for selective α-scission of the P(OH)R3 radical intermediate

  光诱导产生正膦基自由基提供了一种通用策略来获取各种具有合成价值的自由基。尽管β-断裂模式已被深入研究，但调节正膦基自由基进行α-断裂途径仍然是一个长期存在的挑战。我们在此开发了一种前所未有的方案，用于在光催化条件下选择性 α-裂解 P(OH)R 3自由基中间体。这种通过 P(OH)R 3自由基的 α-断裂实现的有效 P-C 键断裂已成功用于烯烃的烷基化/氟烷基化。
• Zn-Mediated Scalable Synthesis of Trifluoromethylphosphines from Phosphine Chlorides and CF₃Br
  作者：Deqian Peng、Shouzhi Zhang、Wu Fan、Yuan Wen、Suhua Li

  DOI：10.1021/acs.orglett.3c01253

  日期：2023.6.2

  reported TFMPhos, products from nucleophilic or electrophilic trifluoromethylation of substrates, requiring one or more steps and prepared from phosphine chlorides, are very limited in structure diversity. Herein, we report a convenient and scalable (up to 100 mmol) recipe to synthesize diverse trifluoromethylphosphines via direct radical trifluoromethylation of phosphine chlorides with CF3Br in the presence

  三氟甲基膦是一种稀有的膦，具有独特的吸电子特性，可导致一些独特的反应性。报道的 TFMPhos 是底物的亲核或亲电三氟甲基化产物，需要一个或多个步骤并由氯化膦制备，其结构多样性非常有限。在此，我们报告了一种方便且可扩展（高达 100 mmol）的配方，通过氯化膦与 CF 3 Br 在锌粉存在下的直接自由基三氟甲基化合成多种三氟甲基膦。
• A facile synthesis of 1-H-2,2-difluorovinylphosphorus compounds from 2,2,2-trifluoroethyl trifluoromethanesulfonate and substitutions of their vinylic fluorines
  作者：Junji Ichikawa、Hideharu Jyono、Satoshi Yonemaru、Tatsuo Okauchi、Toru Minami

  DOI：10.1016/s0022-1139(99)00037-8

  日期：1999.7

  2,2-Difluorovinylphosphine as well as its oxide and borane-complex are synthesized in high yields via the P-trifluoroethylation of lithium diphenylphosphide with 2,2,2-trifluoroethyl trifluoromethanesulfonate, followed by dehydrofluorination with potassium tert-butoxide. The reactions of 2,2-difluorovinylphosphine oxide and borane-complex with hydride, S- and N-nucleophiles proceed via an addition-elimination process to afford mono- or nonfluorovinylphosphorus compounds and carbamoylmethylphosphine oxides. (C) 1999 Elsevier Science S.A. All rights reserved.