ethyl (2-oxo-2-phenylethyl)(phenyl)phosphinate | 51104-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2-oxo-2-phenylethyl)(phenyl)phosphinate
• 英文别名: 2-[Ethoxy(phenyl)phosphoryl]-1-phenylethanone
• CAS: 51104-34-8
• 化学式: C₁₆H₁₇O₃P
• 分子量: 288.283
• InChiKey: MTDWPJWDQAEDMU-UHFFFAOYSA-N

物化性质

• 沸点：
  421.6±47.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-二苯乙烯 、 ethyl (2-oxo-2-phenylethyl)(phenyl)phosphinate 在 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 反应 6.0h， 以70%的产率得到ethyl phenyl(2,5,5-triphenyl-4,5-dihydrofuran-3-yl)phosphinate
  参考文献：
  名称：

  Mn(OAc)3-Mediated Synthesis of 3-Phosphonyldihydrofurans from β-Ketophosphonates and Alkenes

  摘要：

  A new, general method for the synthesis of 3-phosphonyldihydrofuran derivatives has been achieved through Mn(OAc)(3)-mediated radical cyclization between beta-ketophosphonates and alkenes. This transformation allows the direct formation of C-C/C-O bonds and the construction of a dihydrofuran ring in one reaction with operational simplicity and excellent functional-group compatibility.

  DOI：

  10.1055/s-0036-1588112
• 作为产物：
  描述：

  ethyl phenyl(phenylethynyl)phosphinate 在 水 、 palladium dichloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以94%的产率得到ethyl (2-oxo-2-phenylethyl)(phenyl)phosphinate
  参考文献：
  名称：

  钯（II）催化的炔基膦酸酯水合为β-酮基膦酸酯

  摘要：

  已开发出一种高效的钯（II）催化的广泛的炔基膦酸酯水合成相应的β-酮膦酸酯的化合物，可在80°C的1，4-二恶烷溶液中获得高收率，而无需使用酸性或碱性助催化剂。所描述的催化系统应提供高毒性汞催化方法的有效替代方法，并在合成程序中有用。

  DOI：

  10.1002/adsc.201200420

文献信息

• Copper catalyzed one-pot synthesis of β-ketophosphine oxides from ketones and H-phosphine oxides
  作者：Zhi-Jie Zhang、Dong Yi、Qiang Fu、Wu Liang、Su-Yuan Chen、Lu Yang、Feng-Tian Du、Jian-Xin Ji、Wei Wei

  DOI：10.1016/j.tetlet.2017.05.005

  日期：2017.6

  efficient copper catalyzed one-pot method has been developed for the formation of β-ketophosphine oxides from ketones and H-phosphine oxides under air at room temperature, in which vinylhydrazinedicarboxylate was formed as the key intermediate. Preliminary mechanistic studies indicated that the reaction might involve a radical process and carbonyl oxygen atom of β-ketophosphine oxides came from molecular

  已开发出一种简便有效的铜催化一锅法，用于在室温和空气中由酮和H-膦氧化物形成β-酮膦氧化物，其中乙烯基肼二羧酸酯是关键中间体。初步的机理研究表明，该反应可能涉及自由基过程，β-酮膦氧化物的羰基氧原子来自分子氧。
• Catalytic and Direct Oxyphosphorylation of Alkenes with Dioxygen and H-Phosphonates Leading to β-Ketophosphonates
  作者：Wei Wei、Jian-Xin Ji

  DOI：10.1002/anie.201100219

  日期：2011.9.19

  Direct access: The title reaction has been developed under mild reaction conditions (see scheme; DMSO=dimethyl sulfoxide). This reaction can be effectively scaled up and offers not only a green and attractive approach to β‐ketophosphonates, but also a useful example of direct incorporation of an oxygen atom from dioxygen into organic frameworks.

  直接访问：标题反应已在温和的反应条件下进行（请参阅方案； DMSO =二甲基亚砜）。该反应可以有效地扩大规模，不仅为β-酮膦酸酯提供了一种绿色且有吸引力的方法，而且还提供了一个将来自双氧的氧原子直接掺入有机骨架的有用实例。
• Copper-catalyzed tandem phosphination–decarboxylation–oxidation of alkynyl acids with H-phosphine oxides: a facile synthesis of β-ketophosphine oxides
  作者：Pengbo Zhang、Liangliang Zhang、Yuzhen Gao、Jian Xu、Hua Fang、Guo Tang、Yufen Zhao

  DOI：10.1039/c5cc01904d

  日期：——

  The general method for the tandem phosphination–decarboxylation–oxidation of alkynyl acids under aerobic conditions has been developed.

  烯丙酸的串联磷化-脱羧-氧化反应的一般方法已经开发出来。
• β-Ketophosphonates formation via deesterification or deamidation of cinnamyl/alkynyl carboxylates or amides with H-phosphonates
  作者：Yao Zhou、Mingxin Zhou、Ming Chen、Jihu Su、Jiangfeng Du、Qiuling Song

  DOI：10.1039/c5ra23950h

  日期：——

  We report here an unprecedented Fe/Cu synergistically catalyzed deesterificative or deamidative oxyphosphorylation of unsaturated carboxylates or amides with H-phosphonates.

  我们在这里报告了一种前所未有的Fe/Cu协同催化的不酯化或去酰胺氧磷酰化反应，用于不饱和羧酸盐或酰胺与H-膦酸酯的反应。
• Substituent-Controlled Chemoselective Cleavage of C═C or C_sp²–C(CO) Bond in α,β-Unsaturated Carbonyl Compounds with H-Phosphonates Leading to β-Ketophosphonates
  作者：Yao Zhou、Changqing Rao、Shaoyu Mai、Qiuling Song

  DOI：10.1021/acs.joc.5b02887

  日期：2016.3.4

  An unprecedented substituent-controlled chemoselective cleavage of C═C double bond or C(sp2)–C(CO) bond along with aerobic phosphorylation of α,β-unsaturated carbonyl compounds with H-phosphonates through a radical process has been disclosed. The current strategy provides an access to β-ketophosphonates under mild conditions with a wide substrate scope.

  揭示了前所未有的取代基控制的C═C双键或C（sp 2）–C（CO）键的化学选择性裂解，以及通过自由基过程与H，膦酸酯对α，β-不饱和羰基化合物的需氧磷酸化。当前的策略提供了在较宽的底物范围内在温和条件下获得β-酮膦酸酯的途径。