(+/-)-dimethyl hydroxy(4-cyanophenyl)methylphosphonate

• 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: (+/-)-dimethyl hydroxy(4-cyanophenyl)methylphosphonate
• 英文别名: 4-[Dimethoxyphosphoryl(hydroxy)methyl]benzonitrile
• 化学式: C₁₀H₁₂NO₄P
• 分子量: 241.183
• InChiKey: VOGVRNUKZFURMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氰基苯甲醛 、 三甲氧基磷 在 amberlyst-15 、 水 作用下， 反应 1.75h， 以65%的产率得到(+/-)-dimethyl hydroxy(4-cyanophenyl)methylphosphonate
  参考文献：
  名称：

  Amberlyst-15 as a Heterogeneous Reusable Catalyst for the Synthesis of α-Hydroxy Phosphonates in Water

  摘要：

  在 Amberlyst-15 的存在下，通过醛与三甲基亚磷酸酯在水中的反应，实现了δ-羟基膦酸盐的高效而简单的合成。在温和的条件下，该反应具有高选择性和出色的产率。

  DOI：

  10.1055/s-2007-985595

文献信息

• [EN] BICYCLIC PYRAZOLES AS PROTEIN KINASE INHIBITORS<br/>[FR] PYRAZOLES BICYCLIQUES EN TANT QU'INHIBITEURS DE PROTÉINES KINASES
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2010070060A1

  公开（公告）日：2010-06-24

  3,4-diaryl-bicyclicpyrazole derivatives of formula (I) as defined in the specification, and pharmaceutically acceptable salts thereof, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be useful, in therapy, in the treatment of diseases associated with a disregulated protein kinase activity, like cancer.

  公开了规范中定义的式(I)的3,4-二芳基-双环吡唑衍生物及其药学上可接受的盐，其制备方法和包含它们的药物组合物；发明的化合物可能在治疗中对治疗与蛋白激酶活性失调相关的疾病，如癌症，具有用处。
• [EN] 3,4-DIARYLPYRAZOLES AS PROTEIN KINASE INHIBITORS<br/>[FR] 3,4-DIARYLPYRAZOLES UTILISÉS COMME INHIBITEURS DE PROTÉINE KINASE
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2010010154A1

  公开（公告）日：2010-01-28

  3,4-diarylpyrazole derivatives of formula (I) as defined in the specification, and pharmaceutically acceptable salts thereof, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be useful, in therapy, in the treatment of diseases associated with a disregulated protein kinase activity, like cancer.

  公开了规范中定义的式(I)的3,4-二芳基吡唑衍生物及其药用盐，其制备方法和包含它们的药物组合物；发明的化合物可能在治疗中对治疗与蛋白激酶活性失调相关的疾病，如癌症，具有用处。
• Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst
  作者：Makarand A. Kulkarni、Uday P. Lad、Uday V. Desai、Satish D. Mitragotri、Prakash P. Wadgaonkar

  DOI：10.1016/j.crci.2012.10.009

  日期：2013.2

  Résumé An extremely simple, high yielding, highly rapid and solvent-free protocol has been described for hydrophosphylation of aldehydes using potassium phosphate as catalyst. Easy commercial availability of the reusable catalyst, operational simplicity at ambient temperature and avoidance of conventional work-up as well as purification procedure makes this solvent-free protocol a near-ideal synthesis. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.pdf

  摘要 描述了一种极其简单、高产量、高速且无溶剂的醛类羟基磷化方法，使用磷酸钾作为催化剂。该可重复使用的催化剂易于商业获取，在常温下操作简单，并且避免了传统的后处理和纯化过程，使该无溶剂方案成为一种近乎理想的合成方法。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.pdf
• Biocatalytic Promiscuity of Lipases in Carbon‐Phosphorus Bond Formation
  作者：Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1002/cctc.201900397

  日期：2019.5.20

  A promiscuous lipase‐catalyzed carbon‐phosphorus bond formation is presented. The developed enzymatic Pudovik‐Abramov reaction of various aromatic and aliphatic aldehydes with dialkyl phosphonates provides biologically and pharmacologically relevant α‐hydroxy phosphonates with the yields from 11 % to 85 %. The developed protocol proceeds in the presence of porcine pancreas lipase under environmentally

  提出了混杂的脂肪酶催化的碳-磷键形成。各种芳香族和脂肪族醛与二烷基膦酸酯的发达的酶促Pudovik‐Abramov反应可提供生物学上和药理学上相关的α-羟基膦酸酯，产率为11％至85％。所开发的方案在环境可持续的条件下在猪胰腺脂肪酶存在下进行。研究了包括酶来源，有机溶剂和温度在内的反应条件对反应过程的影响。制定的协议适用于多种醛，包括与合成有关的杂环糠醛和2-噻吩甲醛。
• Magnetic Fe₃O₄Nanoparticle-Supported Phosphotungstic Acid as a Recyclable Catalyst for the Kabachnik-Fields Reaction of Isatins, Imines, and Aldehydes under Solvent-Free Conditions
  作者：Mohd Nazish、S. Saravanan、Noor-ul H. Khan、Prathibha Kumari、Rukhsana I. Kureshy、Sayed H. R. Abdi、Hari C. Bajaj

  DOI：10.1002/cplu.201402191

  日期：2014.9.22

  reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α‐hydroxy and α‐amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle

  磁性纳米颗粒负载的磷钨酸已被用于以亚磷酸二甲酯和亚磷酸二乙酯为亲核试剂，有效地催化靛红，亚胺和醛的加氢膦酰化反应，从而在宽范围内以优异的收率得到相应的α-羟基和α-氨基膦酸酯。的基板。反应条件简单，绿色，高效。在保持活性的情况下，将催化剂再循环至五次。基于NMR光谱学研究，提出了可能的催化循环。