diphenyl (2-nitro-1-phenylethyl)phosphonate | 922729-59-7

• 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-nitro-1-phenylethyl)phosphonate
• 英文别名: Diphenyl (2-nitro-1-phenylethyl)phosphonate；(1-diphenoxyphosphoryl-2-nitroethyl)benzene
• CAS: 922729-59-7
• 化学式: C₂₀H₁₈NO₅P
• 分子量: 383.34
• InChiKey: ITPPSYRSWOHXQN-UHFFFAOYSA-N

物化性质

• 熔点：
  153.8-153.9 °C
• 沸点：
  530.4±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  β-硝基苯乙烯 、 亚磷酸二苯酯 在 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate 作用下， 以89%的产率得到diphenyl (2-nitro-1-phenylethyl)phosphonate
  参考文献：
  名称：

  Ionic Liquid–Promoted Phospha-Michael Reaction: Convenient Access to β-Nitrophosphonates

  摘要：

  A convenient and mild procedure is developed for -nitrophosphonates via phospha-Michael addition of phosphites to nitrostyrene at room temperature in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU)-based ionic liquid [DBUH][OAc]. The operational simplicity, convenient workup, and reusability of the ionic liquid make this method attractive.

  DOI：

  10.1080/00397911.2015.1064138

文献信息

• P–C Bond formation via direct and three-component conjugate addition catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)
  作者：Zhiyong Jiang、Yan Zhang、Weiping Ye、Choon-Hong Tan

  DOI：10.1016/j.tetlet.2006.11.019

  日期：2007.1

  The direct addition of P(O)–H bonds (dialkyl phosphites and diphenyl phosphonite) across various activated alkenes was catalyzed effectively by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). This is a mild, rapid and efficient protocol to generate P–C bonds. This simple procedure allows a series of dialkyl alkylphosphonates and trisubstituted phosphine oxides to be prepared in high yields. Further investigation

  1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD）有效地催化了各种活化烯烃之间直接添加的P（O）-H键（亚磷酸二烷基酯和亚磷酸二苯酯）。这是生成P–C键的温和，快速且有效的协议。这种简单的方法可以高收率制备一系列的烷基二膦酸烷基酯和三取代的氧化膦。进一步的研究导致了方便的一锅三组分反应，该反应包含二苯基亚膦酸酯，丙二腈和醛。
• Quinine-Catalyzed Enantioselective Michael Addition of Diphenyl Phosphite to Nitroolefins: Synthesis of Chiral Precursors of α-Substituted β-Aminophosphonates
  作者：Jian Wang、Lora D. Heikkinen、Hao Li、Liansuo Zu、Wei Jiang、Hexin Xie、Wei Wang

  DOI：10.1002/adsc.200600429

  日期：2007.5.7

  nitroalkenes has been developed. This methodology affords a facile access to enantiomerically enriched β-nitrophosphates, precursors for the preparation of synthetically and biologically useful β-aminophosphonates.

  已经开发了由奎宁促进的亚磷酸二苯酯与硝基烯烃的对映选择性迈克尔加成反应。该方法提供了对映异构体富集的β-硝基磷酸酯的简便方法，β-硝基磷酸酯是制备合成和生物学上有用的β-氨基膦酸酯的前体。
• Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes
  作者：Ana Alcaine、Eugenia Marqués-López、Pedro Merino、Tomás Tejero、Raquel P. Herrera

  DOI：10.1039/c0ob01059f

  日期：——

  Bifunctional thiourea catalyzes the enantioselective Michael addition reaction of diphenyl phosphite to nitroalkenes. This methodology provides a facile access to enantiomerically enriched β-nitrophosphonates, precursors for the preparation of synthetically and biologically useful β-aminophosphonic acids. DFT level of computational calculations invoke the attack of the diphenyl phosphite to the nitroolefin

  双功能 硫脲 催化对映体的迈克尔对映选择性迈克尔加成反应 亚磷酸二苯酯硝基烯烃。该方法提供了对映异构体富集的β-硝基膦酸酯的便捷途径，β-硝基膦酸酯是制备合成和生物学上有用的β-氨基膦酸的前体。DFT级别的计算计算会引起Re面对亚磷酸二苯酯对硝基烯烃的攻击，这为文献中这一鲜为人知的过程更新提供了光明。计算结果支持在最终加合物中获得的绝对构型。
• TRANSITION METAL COMPLEXES FOR ENANTIOSELECTIVE CATALYSIS OF CARBON-CARBON, CARBON-HETEROATOM, AND CARBON-HYDROGEN BOND FORMING REACTIONS
  申请人：THE TEXAS A&M UNIVERSITY SYSTEM

  公开号：US20150165429A1

  公开（公告）日：2015-06-18

  In some embodiments, the present disclosure pertains to a compound, comprising a transition metal complex having the formula Φ-[M(x,y)-L 1 (w,v)-L 2 (t,u)-L 3 ] p+ An − m Z − p — m . In an embodiment of the present disclosure Φ may be A. In another embodiment Φ may be Δ. In some embodiments of the present disclosure, M is a transition metal. In a related embodiment, p is an integer corresponding to the oxidation state of M. In some embodiments of the present disclosure, each of x, y, w, v, t, and u independently comprise R. In other embodiments, each of x, y, w, v, t, and u independently comprise S. In an embodiment of the present disclosure, each of L 1 , L 2 , and L 3 independently is a ligand comprising a substituted diamine. In some embodiments, An″ comprises a lipophilic anion, where m is from 1 to 3, and where Z − comprises an optional second anion.

  在某些实施例中，本公开涉及一种化合物，包括具有公式Φ-[M（x，y）-L1（w，v）-L2（t，u）-L3]p+An−mZ−p—m的过渡金属配合物。在本公开的某种实施例中，Φ可以是A。在另一种实施例中，Φ可以是Δ。在本公开的某些实施例中，M是一种过渡金属。在相关实施例中，p是与M的氧化态相对应的整数。在本公开的某些实施例中，x，y，w，v，t和u中的每个都独立地包括R。在其他实施例中，x，y，w，v，t和u中的每个都独立地包括S。在本公开的某种实施例中，L1、L2和L3中的每个都独立地是包含取代二胺的配体。在某些实施例中，An″包括一个亲脂性阴离子，其中m从1到3，而Z−包括一个可选的第二个阴离子。
• Transition metal complexes for enantioselective catalysis of carbon-carbon, carbon-heteroatom, and carbon-hydrogen bond forming reactions
  申请人：Lewis Kyle G.

  公开号：US10189871B2

  公开（公告）日：2019-01-29

  In some embodiments, the present disclosure pertains to a compound, comprising a transition metal complex having the formula Φ-[M (x,y)-L1 (w,v)-L2 (t,u)-L3]p+An−mZ−p−m. In an embodiment of the present disclosure Φ may be Λ. In another embodiment Φ may be Δ. In some embodiments of the present disclosure, M is a transition metal. In a related embodiment, p is an integer corresponding to the oxidation state of M. In some embodiments of the present disclosure, each of x, y, w, v, t, and u independently comprise R. In other embodiments, each of x, y, w, v, t, and u independently comprise S. In an embodiment of the present disclosure, each of L1, L2, and L3 independently is a ligand comprising a substituted diamine. In some embodiments, An− comprises a lipophilic anion, where m is from 1 to 3, and where Z− comprises an optional second anion.

  在一些实施方案中，本公开涉及一种化合物，该化合物包含具有式 Φ-[M (x,y)-L1 (w,v)-L2 (t,u)-L3]p+An-mZ-p-m 的过渡金属配合物。在本公开的一个实施方案中，Φ 可以是Λ。在本公开的一些实施方案中，M 是过渡金属。在本公开的一些实施方案中，x、y、w、v、t和u中的每一个独立地包括R。在其它实施方案中，x、y、w、v、t和u中的每一个独立地包括S。在本公开的一个实施方案中，L1、L2和L3中的每一个独立地是包括取代二胺的配体。在一些实施方案中，An-包括亲脂阴离子，其中m为1至3，Z-包括任选的第二阴离子。