diphenyl allylphosphonate | 101111-39-1

• 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: diphenyl allylphosphonate
• 英文别名: Phosphonic acid, 2-propenyl-, diphenyl ester；[phenoxy(prop-2-enyl)phosphoryl]oxybenzene
• CAS: 101111-39-1
• 化学式: C₁₅H₁₅O₃P
• 分子量: 274.256
• InChiKey: INDCZXZNLPWHJP-UHFFFAOYSA-N

物化性质

• 沸点：
  178-180 °C(Press: 5 Torr)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diphenyl allylphosphonate 在 Grubbs catalyst first generation 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-phenoxy-3,6-dihydro-1,2-oxaphosphinine 2-oxide
  参考文献：
  名称：

  Synthesis of Cyclic Phosphonate Analogues of (Lyso)phosphatidic Acid Using a Ring-Closing Metathesis Reaction

  摘要：

  We describe a versatile and efficient method for the preparation of acyloxy-substituted six-membered cyclic phosphonates using the ring-closing metathesis. After closure, the key cyclic phosphonate intermediate was dihydroxylated and converted to a new class of conformationally constrained PA and LPA analogues. The oleoyloxy-substituted cyclic phosphonate 4 had unique receptor-selective properties as a ligand, showing partial activation of the LPA(2) GPCR and weak antagonism of the LPA(1) GPCR.

  DOI：

  10.1021/jo0607919
• 作为产物：
  描述：

  phosphorous acid allyl ester-diphenyl ester 在 四氯化碳 作用下， 生成 diphenyl allylphosphonate
  参考文献：
  名称：

  Kamai; Charrasowa, Metodiceskij sbornik, 1957, # 23, p. 122,126

  摘要：

  DOI：

文献信息

• Method and compositions for identifying anti-HIV therapeutic compounds
  申请人：GILEAD SCIENCES, INC.

  公开号：US20040121316A1

  公开（公告）日：2004-06-24

  Methods are provided for identifying anti-HIV therapeutic compounds substituted with carboxyl ester or phosphonate ester groups. Libraries of such compounds are screened optionally using the novel enzyme GS-7340 Ester Hydrolase. Compositions and methods relating to GS-7340 Ester Hydrolase also are provided.

  提供了一种鉴定含有羧酸酯或磷酸酯基团抗HIV治疗化合物的方法。可以选择使用新型酶GS-7340酯水解酶筛选这类化合物的文库。还提供了与GS-7340酯水解酶相关的组合物和方法。
• <i>P</i>-Heterocyclic Building Blocks:  Application to the Stereoselective Synthesis of <i>P-</i>Sugars
  作者：Diana S. Stoianova、Alan Whitehead、Paul R. Hanson

  DOI：10.1021/jo0505122

  日期：2005.7.1

  the utilization of stereoselective additions to allyldiphenylphosphonate esters and subsequent ring-closing metathesis (RCM) to access P-chiral P-heterocyclic building blocks for the synthesis of phosphono sugars is described. These building blocks possess several attractive components, including the following: (i) P(2) and C(6) stereogenic centers for directing stereoselective transformations; (ii)

  一种策略是利用对烯丙基二苯基膦酸酯的立体选择性加成以及随后的闭环复分解（RCM）来获得P-手性P描述了用于合成膦酰基糖的-杂环结构单元。这些构件具有几个有吸引力的组成部分，其中包括：（i）用于指导立体选择性转化的P（2）和C（6）立体生成中心；（ii）活化的C（3）亚甲基，其促进碱介导的烯烃转座以产生可用于进一步的立体选择性反应的乙烯基膦酸酯；（iii）一个P（2）-立体异构中心，该中心含有可交换的膦酸酯，可以减弱磷的“立体化学环境”。归纳起来，这些属性有助于简明的方法，用于立体选择性地合成P糖阵列。
• Hydroboration of Unsaturated Phosphonic Esters:  Synthesis of Boronophosphonates and Trisubstituted Vinylphosphonates
  作者：Inna Pergament、Morris Srebnik

  DOI：10.1021/ol006836o

  日期：2001.1.1

  [figure: see text] Hydroboration of vinyl phosphonates with pinacolborane (PBH) proceeds to give phosphonoboronates, 2. Surprisingly, such compounds have not been reported before. The reaction works well with terminal alkenylphosphonates. Internal alkenylphosphonates give complex mixtures. Hydroboration/Suzuki coupling of alkynylphosphonates, with PBH, in a one-pot procedure gives trisubstituted vinylphosphonates

  [图：见正文]用频哪醇硼烷（PBH）对膦酸乙烯基酯进行氢硼化可得到膦酰基硼酸酯2。令人惊讶的是，此类化合物以前尚未见报道。该反应与末端烯基膦酸酯一起很好地进行。内部链烯基膦酸酯产生复杂的混合物。单锅法将炔基膦酸酯与PBH进行硼氢化/铃木偶联，可得到具有良好总收率的三取代乙烯基膦酸酯，并提供了这些化合物的新合成方法。
• Towards a characterization of the structural determinants of specificity in the macrocyclizing thioesterase for deoxyerythronolide B biosynthesis
  作者：Panos Argyropoulos、Fabien Bergeret、Christophe Pardin、Janice M. Reimer、Atahualpa Pinto、Christopher N. Boddy、T. Martin Schmeing

  DOI：10.1016/j.bbagen.2015.11.007

  日期：2016.3

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  I型聚酮化合物合酶（PKS）是巨大的多域蛋白，可合成许多治疗剂和其他天然产物。合成通过硫代模板机理进行，其中中间体共价附于PKS。最终的聚酮化合物的释放是通过末端硫酯酶（TE）域通过水解，酯交换或大环化来催化的。PKS 6-脱氧赤藓醇B合酶（DEBS）产生具有临床意义的抗生素红霉素的14元大环内酯核心。DEBS的TE结构域（DEBS TE）对天然和修饰底物的水解或大环化具有公认的，经验确定的特异性。我们目前正在努力了解使用一组新颖的二苯基烷基膦酸酯在DEBS TE中硫酯酶反应特异性的结构基础，模拟由DEBS TE专门环化或水解的底物。我们已经确定了仅在1.7Å处的DEBS TE的新构建体的结构，并且以2.1Å的分辨率与简单的烯丙基膦酸酯结合的DEBS TE。其他更复杂的二苯基烷基膦酸酯会抑制DEBS TE，但我们无法可视化这些与DEBS TE配合的忠实环化类似物。这项工作代表着使用与复杂底物类似物复合的DEBS
• BONDABLE FLAME-RETARDANT VANILLIN-DERIVED MOLECULES
  申请人：International Business Machines Corporation

  公开号：US20180320073A1

  公开（公告）日：2018-11-08

  A flame-retardant vanillin-derived molecule, a process for forming a flame-retardant resin, and an article of manufacture comprising a material that contains the flame-retardant vanillin-derived molecule are disclosed. The flame-retardant vanillin-derived molecule can be synthesized from vanillin obtained from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety with phenyl, allyl, epoxide, propylene carbonate, or thioether substituents. The process for forming the flame-retardant resin can include reacting a vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived molecule, and binding the flame-retardant vanillin-derived molecule to a resin. The flame-retardant vanillin-derived molecules can also be bound to polymers. The material in the article of manufacture can be flame-retardant, and contain the flame-retardant vanillin-derived molecules. Examples of materials that can be in the article of manufacture can include resins, plastics, adhesives, polymers, etc.

  本文揭示了一种阻燃香草醛衍生分子、形成阻燃树脂的方法，以及包含含有阻燃香草醛衍生分子的材料的制造物品。这种阻燃香草醛衍生分子可以从生物基来源中获得的香草醛合成，可以具有至少一个含有苯基、烯丙基、环氧、丙烯碳酸酯或硫醚取代基的磷酸酯或膦酰基团。形成阻燃树脂的方法可以包括将香草醛衍生物和阻燃磷基分子反应以形成阻燃香草醛衍生分子，并将其与树脂结合。阻燃香草醛衍生分子也可以与聚合物结合。制造物品中的材料可以是阻燃的，并含有阻燃香草醛衍生分子。制造物品中的材料可以包括树脂、塑料、粘合剂、聚合物等。