methyl-phosphonic acid benzyl methyl ester | 710-09-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: methyl-phosphonic acid benzyl methyl ester
• 英文别名: benzyl methyl methanephosphonate；benzyl methyl methylphosphonate；Methyl-phosphorsaeure-benzylester-methylester；Methylphosphonsaeure-benzylester-methylester；[Methoxy(methyl)phosphoryl]oxymethylbenzene
• CAS: 710-09-8
• 化学式: C₉H₁₃O₃P
• 分子量: 200.174
• InChiKey: RVLZUJLMBPOAIB-UHFFFAOYSA-N

物化性质

• 沸点：
  159 °C(Press: 13 Torr)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  methyl-phosphonic acid benzyl methyl ester 在 奎宁环 、 草酰氯 作用下， 生成 甲基氯膦酸甲酯
  参考文献：
  名称：

  从相应的苄基酯方便地“一锅”合成氯代膦酸酯，氯代磷酸酯和氯代磷酰胺

  摘要：

  使用奎尼丁对烷基膦酸酯，磷酸酯和磷酰胺苄基酯进行选择性单脱保护，然后对后续的盐进行氯化，可以方便的“一锅法”制备各种烷基膦酰氯，一氯磷酸酯和一氯磷酰胺。

  DOI：

  10.1016/0040-4039(95)00865-a
• 作为产物：
  描述：

  亚磷酸二苄酯 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl-phosphonic acid benzyl methyl ester
  参考文献：
  名称：

  Synthesis of carbapenem-3-phosphonic acid derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)81403-3

文献信息

• Alternatives to 1-H-tetrazole in the preparation of phosphonate diesters and phosphonamidates from phosphonyl dichlorides
  作者：Jack Maung、Jeremy P. Mallari、Cindy J. Choy、Clifford E. Berkman

  DOI：10.1016/j.tetlet.2004.06.083

  日期：2004.8

  5-Ethylthio-1-H-tetrazole (SET) and 4,5-dicyanoimidazole (DCI) were examined as alternatives to 1-H-tetrazole to mediate the synthesis of phosphonate diesters and phosphonamidates from phosphonyl dichlorides through a two-step one-pot reaction in various organic solvents. SET and DCI were comparable to 1-H-tetrazole for catalyzing these reactions. SET afforded slightly greater yields than DCI while

  研究了5-乙硫基-1 - H-四唑（SET）和4,5-二氰基咪唑（DCI）作为1- H-四唑的替代品，以通过两步式一价反应从膦酰二氯化物介导膦酸酯二酯和膦酰胺的合成。在各种有机溶剂中进行罐式反应。SET和DCI在催化这些反应方面与1- H-四唑相当。SET的收率略高于DCI，而苯通常是该反应的最佳溶剂。
• Alkali Metal Alkoxide Clusters:  Convenient Catalysts for the Synthesis of Methylphosphonates
  作者：Rebecca M. Kissling、Michel R. Gagné

  DOI：10.1021/jo9820521

  日期：1999.3.1

  interchange reaction between carbonyl and phosphorus esters. This reactivity leads to convenient methodologies for the synthesis of symmetric and unsymmetric alkyl-substituted methylphosphonates from dimethyl methylphosphonate (DMMP). Reactions rates are high with initial turnover frequencies (N(t)) in excess of 1 x 10(6) h(-)(1) observed and with KO(t)Bu > NaO(t)Bu > LiO(t)Bu. The reactions were sensitive

  碱金属醇盐是用于促进羰基酯和磷酸酯之间的交换反应的良好催化剂（1-8 mol％）。这种反应性导致了由甲基膦酸二甲酯（DMMP）合成对称和不对称烷基取代的甲基膦酸酯的简便方法。初始转换频率（N（t））超过1 x 10（6）h（-）（1）且KO（t）Bu> NaO（t）Bu> LiO（t）Bu时，反应速率很高。反应对产物甲基膦酸酯中的空间效应敏感，反应速率与转移醇盐的大小平行（正烷基>异烷基>叔烷基）。对于测试反应DMMP +乙酸异丙酯，取代动力学与依次替换每种甲醇的情况一致，并且第二位移的替代率明显低于第一位移。第一次取代过程的动力学研究表明了浓度依赖性速率定律。一种最容易解决的方案是偶联酯交换反应，其中醇盐可逆地独立地添加到膦酸酯和酯中。
• Synthesis of phosphorus esters by transesterification mediated by N-heterocyclic carbenes (NHCs)
  作者：Rohit Singh、Steven P. Nolan

  DOI：10.1039/b509783e

  日期：——

  The versatile nucleophilic organic catalysts N-heterocyclic carbenes (NHCs) have been shown to effectively mediate the transesterification of phosphorus esters under mild conditions; user-friendly imidazolium salts can also be employed as pre-catalysts.

  通用的亲核有机催化剂N-杂环卡宾（NHCs）在温和的条件下可有效介导磷酸酯的酯交换反应。用户友好的咪唑鎓盐也可以用作预催化剂。
• Thuong,N.T. et al., Bulletin de la Societe Chimique de France, 1965, p. 1925 - 1930
  作者：Thuong,N.T. et al.

  DOI：——

  日期：——
• Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway
  作者：Emmanuel Klein、Hoàng-Oanh Nghiêm、Alain Valleix、Charles Mioskowski、Luc Lebeau

  DOI：10.1002/1521-3765(20021018)8:20<4649::aid-chem4649>3.0.co;2-m

  日期：2002.10.18

  Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebisphosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.