diethyl 3-oxo-1,3-diphenylpropylphosphonate | 195324-59-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: diethyl 3-oxo-1,3-diphenylpropylphosphonate
• 英文别名: 3-Diethoxyphosphoryl-1,3-diphenylpropan-1-one
• CAS: 195324-59-5
• 化学式: C₁₉H₂₃O₄P
• 分子量: 346.363
• InChiKey: WKMLQTBEOVXDIG-UHFFFAOYSA-N

物化性质

• 沸点：
  489.7±45.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 3-oxo-1,3-diphenylpropylphosphonate 、 氰乙酸乙酯 在 sulfur 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以55%的产率得到2-Amino-5-[(diethoxy-phosphoryl)-phenyl-methyl]-4-phenyl-thiophene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthese de 2-Amino-5-(phosphonomethyl) Thiophenes

  摘要：

  The reaction of gamma-ketophosphonates (1) under bar with malonic derivatives and sulfur in basic conditions leads to 2-amino-5-(phosphonomethyl)thiophenes (2) under bar. The structure of compounds 2 was confirmed by NMR and IR spectroscopy and in some cases by mass spectrometry.

  DOI：

  10.1080/10426500500269844
• 作为产物：
  描述：

  苯亚甲基苯乙酮 、 亚磷酸三乙酯 在 溶剂黄146 作用下， 以100%的产率得到diethyl 3-oxo-1,3-diphenylpropylphosphonate
  参考文献：
  名称：

  Petnehazy, Imre; Jaszay, Zsuzsa M.; Toeke, Laszlo, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 103 - 106

  摘要：

  DOI：

文献信息

• Potassium Carbonate Promoted Nucleophilic Addition of Alkenes with Phosphites
  作者：Shengmei Guo、Zhenjun Huang、Wei Liu、Sen Li、Yutian Yang、Hu Cai

  DOI：10.1055/s-0040-1707852

  日期：2020.8

  A facile hydrophosphonylation of alkenes by phosphites promoted by potassium carbonate was developed. The reaction features include easy handling, environmental friendliness, and avoidance of the use of strong bases. A variety of alkenes are tolerated in this reaction, with moderate to excellent yields.

  开发了一种由碳酸钾促进的亚磷酸酯对烯烃的轻松氢膦酰化。反应特点包括易于处理、环境友好和避免使用强碱。该反应可以耐受多种烯烃，产率中等至极好。
• Novel Lanthanide Amides Incorporating Neutral Pyrrole Ligand in a Constrained Geometry Architecture: Synthesis, Characterization, Reaction, and Catalytic Activity
  作者：Fenhua Wang、Shaowu Wang、Xiancui Zhu、Shuangliu Zhou、Hui Miao、Xiaoxia Gu、Yun Wei、Qingbing Yuan

  DOI：10.1021/om400409x

  日期：2013.7.22

  The first series of lanthanide amido complexes incorporating a neutral pyrrole ligand in a constrained geometry architecture were synthesized, and their bonding, reactions, and catalytic activities were studied. Treatment of [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 with 1 equiv of (N-C6H5NHCH2CH2)(2,5-Me2C4H2N) (1) afforded the first example of bisamido lanthanide complexes having the neutral pyrrole η5-bonded

  合成了在受限几何结构中结合中性吡咯配体的第一系列镧系酰胺配合物，并研究了它们的键合，反应和催化活性。的治疗[（ME 3 Si）的2 N] 3 LN（μ-Cl）的锂（THF）3与1的（当量Ñ -C 6 ħ 5 NHCH 2 CH 2）（2,5-ME 2 c ^ 4 ħ 2 N）（1），得到具有中性吡咯η双酰胺镧系络合物的第一例5键合的，以配制成[η金属5：η 1-（N -C 6 H 5 NCH 2 CH 2）（2,5-Me 2 C 4 H 2 N）] Ln [N（SiMe 3）2 ] 2（Ln = La（2）和Nd（3）） 。的反应[（ME 3 Si）的2 N] 3的Sm（μ-Cl）的锂（THF）3与2当量的1产生的复杂的[η 5：η 1 - （Ñ -C 6 ħ 5 NCH 2 CH 2） （2,5-我2c ^ 4 ħ 2 N）] [η 1 - （Ñ -C 6 ħ 5 NCH 2 CH 2）（2
• PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes
  作者：Giacomo Strappaveccia、Luca Bianchi、Simone Ziarelli、Stefano Santoro、Daniela Lanari、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1039/c6ob00242k

  日期：——

  PS-BEMP was used as a heterogeneous catalyst for the phospha-Michael addition of phosphorus nucleophiles to a variety of electron-poor alkenes. The addition reactions were generally performed with equimolar amounts of reagents under solvent free conditions. The protocol proved to be very efficient for the addition to aromatic, non-aromatic and cyclic ketones, giving good yields (78–85%) in all cases

  PS-BEMP用作非均相催化剂，用于将磷亲核体的磷-迈克尔加成到各种电子贫乏的烯烃中。加成反应通常在无溶剂条件下用等摩尔量的试剂进行。事实证明，该方案对于添加芳族，非芳族和环状酮非常有效，在所有情况下均具有良好的收率（78-85％）。该方案还扩展到了α，β-不饱和酯和腈，并获得了良好的结果。这表明PS-BEMP是将磷-迈克尔加成至电子贫乏烯烃的良好催化剂。
• Highly Enantioselective 1,4-Addition of Diethyl Phosphite to Enones Using a Dinuclear Zn Catalyst
  作者：Depeng Zhao、Ye Yuan、Albert S. C. Chan、Rui Wang

  DOI：10.1002/chem.200802688

  日期：2009.3.9

  Zinc benefits: The first catalytic asymmetric phospha‐Michael addition of enones has been developed. Under mild reaction conditions, the γ‐oxo phosphonates could be obtained in high yields (up to 99 %) with excellent enantioselectivities (93–99 % ee; see scheme). The strategy makes the asymmetric synthesis of biologically important phosphonate compounds more accessible.

  锌的优点：首次开发了烯酮的催化不对称磷酸-迈克尔加成反应。在温和的反应条件下，可以以高收率（高达99％）和出色的对映选择性（93–99％ee；参见方案）获得γ-氧代膦酸酯。该策略使生物学上重要的膦酸酯化合物的不对称合成更容易实现。
• Generation and Application of Homoenolate Equivalents Utilizing [1,2]-Phospha-Brook Rearrangement under Brønsted Base Catalysis
  作者：Azusa Kondoh、Takuma Aoki、Masahiro Terada

  DOI：10.1002/chem.201605673

  日期：2017.2.24

  A new method for catalytic generation of a homoenolate equivalent and its application to carbon−carbon bond formation was developed by utilizing the [1,2]‐phospha‐Brook rearrangement under Brønsted base catalysis. The α‐oxygenated allyl anions, which can serve as homoenolate equivalents, were catalytically generated in situ by treating readily available chalcones with diethyl phosphite or the pre‐formed

  利用布朗斯台德碱催化下的[1,2]-磷-布鲁克重排反应，开发了一种催化均烯酸酯当量的新方法及其在碳-碳键形成中的应用。α-氧化的烯丙基阴离子可以用作均烯酸酯当量，它是通过在催化量的三氯甲烷存在下，用亚磷酸二乙酯处理易得的查耳酮或用查耳酮处理预先形成的亚磷酸二乙酯的1,2-加合物来原位催化生成的。磷腈碱P2- t Bu。所得的烯丙基阴离子随后被各种亲电试剂（包括迈克尔受体，亚胺和醛）捕获，以高收率提供相应的加合物，具有中等至良好的非对映选择性。