3-diphenylphosphinoyl-butan-2-one | 71893-27-1

• 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: 3-diphenylphosphinoyl-butan-2-one
• 英文别名: 3-(Diphenylphosphoryl)butan-2-one；3-diphenylphosphorylbutan-2-one
• CAS: 71893-27-1
• 化学式: C₁₆H₁₇O₂P
• 分子量: 272.284
• InChiKey: HYJPOBPSILDXIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-diphenylphosphinoyl-butan-2-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 26.0h， 生成 4-diphenylphosphinoyl-4,5-dihydro-4,5-dimethylfuran-2(3H)-one
  参考文献：
  名称：

  Torr, Richard S.; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1983, p. 1173 - 1180

  摘要：

  DOI：
• 作为产物：
  描述：

  diphenylphosphine oxide 在 磷酸 作用下， 以 正丁醇 为溶剂， 反应 2.0h， 生成 3-diphenylphosphinoyl-butan-2-one
  参考文献：
  名称：

  Petrov, K. A.; Chauzov, V. A.; Agafonov, S. V., Journal of general chemistry of the USSR, 1983, vol. 53, # 1, p. 42 - 47

  摘要：

  DOI：

文献信息

• Diphenylphosphinoyl-mediated synthesis of ketones
  作者：David J. Fox、Daniel Sejer Pedersen、Stuart Warren

  DOI：10.1039/b606873a

  日期：——

  α-Diphenylphosphinoyl ketones are selectively and sequentially alkylated at the α-position. Double lithiation and selective alkylation occurs at the less stabilised γ-position. Dephosphinoylation of the alkylation products gives ketones. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible. The method is ideally suited for the preparation of acid-sensitive ketones.

  α-二苯基膦酰基酮在α位上选择性且顺序性地进行烷基化。双锂化和选择性烷基化发生在较不稳定的γ位。脱膦酰化得到的烷基化产物是酮。单烷基化具有选择性，形成的中间体晶体高度结晶，且可以进行一步完成的方法。该方法非常适合制备酸敏感的酮。
• Friedländer reaction in the synthesis of 2-(phosphoryl)alkyl-substituted 1,6-naphthyridines
  作者：Pavel S. Lemport、Georgy V. Bodrin、Andrey I. Belyakov、Pavel V. Petrovskii、Anna V. Vologzhanina、Edward E. Nifant’ev

  DOI：10.1016/j.mencom.2009.11.002

  日期：2009.11

  First 2-(phosphoryl)alkyl-substituted 1,6-naphthyridines have been synthesized by the Friedlander reaction between 4-amino-3-formylpyridine and phosphorus-containing ketones; their structures have been confirmed by 1H, 13C and 31P NMR spectroscopy and X-ray diffraction analysis.

  通过2-氨基-3-甲酰基吡啶和含磷酮之间的弗里德兰德反应合成了第一个2-（磷酰基）烷基取代的1，6-萘啶；它们的结构已通过1H，13C和31P NMR光谱法以及X射线衍射分析证实。
• Electrochemical Oxidation‐Induced Oxyphosphorylation of Alkenes and Alkynes with Water via Hydrogen Atom Transfer
  作者：Jianjing Yang、Xue Sun、Kelu Yan、Hongzhao Sun、Shuai Sun、Xiaoyu Jia、Fanjun Zhang、Jiangwei Wen

  DOI：10.1002/adsc.202200421

  日期：2022.8.16

  oxyphosphorylation of alkenes and alkynes with water for β-ketophosphonates has been developed through the radical coupling under electrochemical conditions. This protocol is compatible with a wide range of alkenes, alkynes, and diarylphosphorus derivatives, and enables the gram-scale synthesis of β-ketophosphonates. The mechanistic study revealed that the P radicals were generated via hydrogen atom transfer (HAT)

  已经通过电化学条件下的自由基偶联开发了一种不含金属和外源氧化剂的氧化诱导烯烃和炔烃与水的氧磷酸化反应生成 β-酮膦酸盐。该协议与多种烯烃、炔烃和二芳基磷衍生物兼容，并能够实现克级 β-酮膦酸盐的合成。机理研究表明，P自由基是通过四丁基乙酸铵和阳极氧化过程共同介导的氢原子转移（HAT）事件产生的。
• β-羰基类化合物的制备方法
  申请人：黄淮学院

  公开号：CN116217395A

  公开（公告）日：2023-06-06

  本发明提供了一种β‑羰基类化合物的制备方法，包括：在光和过渡金属协同催化作用和碱性环境下，第一底物及α‑取代酮在反应溶剂中反应合成β‑羰基类化合物；其中，所述第一底物的结构式为：酮酸 亚磺酸钠类化合物 或二取代的膦氧化合物 所述β‑羰基类化合物为1,3‑二羰基化合物 2‑(苯基磺酰)苯乙酮类化合物 或二苯基膦酰苯乙酮类化合物 所以，上述制备方法具有底物普适性、条件温和、操作简单、效率高等特点，且收率可以达到80％以上，可实现同一设备或同一系列设备制备不同的化合物。另外，其底物及催化剂均为商品化试剂，无需特殊制备，原料廉价易得、成本低，有利于工业化应用。
• Opposite Stereochemical Effects Exerted by CeCl3 and TiCl4 on the Lewis Acid Mediated Reduction of α-Alkyl-β-ketophosphine Oxides with Metallic Hydrides: A Highly Stereoselective Protocol for the Synthesis of syn and anti α-alkyl-β-Hydroxyphosphine Oxides
  作者：Giuseppe Bartoli、Marcella Bosco、Letizia Sambri、Renato Dalpozzo、Enrico Marcantoni

  DOI：10.1002/chem.19970031209

  日期：1997.12

  AbstractA general, highly efficient methodology for obtaining both syn and anti β‐hydroxyphosphine oxides by reduction of the corresponding β‐ketophosphine oxides is described. The nature of the Lewis acid was found to be pivotal in determining the outcome of these reactions. Strongly chelating TiCl4 led to the anti isomer in high diastereoisomeric excess in noncoordinating solvents (CH2Cl2) at ‐78°C with BH3/py as reducing agent, while nonchelating CeCl3 gave a high excess of the syn isomer in coordinating solvents (THF) at the same temperature with LiBH4 as reducing agent. In the latter case, CeCl3 is essential in achieving high yields and stereoselectivity, since it allows the reaction to be performed at low temperatures. Otherwise, higher temperatures (0°C) are required, which lower both yields and selectivities. Moreover, each step of the protocol for the synthesis of stereodefined disubstituted olefins from alkylphosphine oxides (Warren's modification of the Horner procedure) has been optimized, and the optimized procedure has been applied to the synthesis of muscalure, the pheromone of the domestic fly.