dibenzyl phenylphosphonate | 19236-61-4

• 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: dibenzyl phenylphosphonate
• 英文别名: [phenyl(phenylmethoxy)phosphoryl]oxymethylbenzene
• CAS: 19236-61-4
• 化学式: C₂₀H₁₉O₃P
• 分子量: 338.343
• InChiKey: DGTUPNAAJLFCEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dibenzyl phenylphosphonate 在 盐酸 、 水 作用下， 反应 0.75h， 生成 苯膦酸
  参考文献：
  名称：

  次膦酸盐和膦酸盐的水解和醇解

  摘要：

  摘要 次膦酸和膦酸有用的中间体和生物活性化合物可以分别由它们的酯制备：次膦酸盐和膦酸盐，通过酸催化水解在常规加热或MW照射下进行。烷基次膦酸盐的酯交换反应仅在合适的离子液体作为催化剂存在的情况下进行。在苯基膦酸盐的情况下，取决于离子液体的性质，酯的形成伴随着 C-O 键的裂变。

  DOI：

  10.1080/10426507.2021.1991345
• 作为产物：
  描述：

  苯膦酰二氯 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 dibenzyl phenylphosphonate
  参考文献：
  名称：

  A convenient two-step one-pot synthesis of phosphonamidates

  摘要：

  Phosphonamidates are formed in high yield from a one-pot sequential reaction of a phosphonyl dichloride with an alcohol and then an amine in the presence of catalytic 1H-tetrazole. Undesired disubstitution of the phoshphonyl dichloride by the alcohol or the amine is minimal due to the presence of tetrazole. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10421-x

文献信息

• An Improved Access to Phosphonic Acids and Their Mono-and Diesters
  作者：Françoise Plénat、Sanusi Ibrahim、Henri-Jean Cristau

  DOI：10.1055/s-1988-27752

  日期：——

  The reaction of phosphonic dichlorides with a mixture of benzyl alcohol and an aliphatic alcohol affords a mixture of the corresponding dibenzyl phosphonate, dialkyl phosphonate, and alkyl benzyl phosphonate which is easily separated by column chromatography to give the pure components. Cleavage of the dibenzyl phosphonate by catalytic hydrogenation affords the phosphonic acid whereas cleavage of the alkyl benzyl phosphonate under the same conditions affords the alkyl hydrogen phosphonate (monoester).

  磷二氯化物的反应与苄醇和脂肪醇混合物提供了相应的二苄基膦酸盐、二烷基膦酸盐和烷基苄基膦酸盐混合物，该混合物通过柱色谱法容易分离得到纯成分。二苄基膦酸盐通过催化氢化裂解得到膦酸，而烷基苄基膦酸盐在相同条件下裂解得到烷基氢膦酸盐（单酯）。
• Hydrolyse Basique de phosphonates I. Étude qualitative
  作者：Henri Christol、Michel̀e Levy、Claude Marty

  DOI：10.1016/s0022-328x(00)88699-4

  日期：1968.6

  The hydrolysis of phosphonates by alkali in aqueous dioxane has been studied. The symmetrical phosphonates are hydrolysed with loss of one ester group to form a monoacid. With the mixed phosphonates the better leaving group is replaced.

  已经研究了在二恶烷水溶液中碱将膦酸酯水解的方法。对称的膦酸酯水解而失去一个酯基，形成一元酸。用混合的膦酸酯，更好的离去基团被取代。
• Palladium-Catalyzed Desulfitative Cross-Coupling Reaction of Sodium Arylsulfinates with H-Phosphonate Diesters
  作者：Tao Miao、Lei Wang

  DOI：10.1002/adsc.201300983

  日期：2014.3.24

  A novel and convenient palladium‐catalyzed cross‐coupling reaction of H‐phosphonate diesters with sodium arylsulfinates was developed via desulfitation in the presence of silver carbonate and tetra‐butylammonium chloride. This method is highly efficient and provides a rapid access to a broad spectrum of arylphosphonate diesters in good to excellent yields.

  通过在碳酸银和氯化四丁基铵的存在下进行脱硫，开发了一种新颖且便捷的钯催化的H膦酸酯二酯与芳基亚磺酸钠的交叉偶联反应。该方法是高效的，并且以良好至优异的产率快速获得广谱的芳基膦酸酯二酯。
• Microwave-Assisted Palladium-Catalyzed Cross-Coupling of Aryl and Vinyl Halides with H-Phosphonate Diesters
  作者：Marcin Kalek、Asraa Ziadi、Jacek Stawinski

  DOI：10.1021/ol801935r

  日期：2008.10.16

  bond was developed. Using a prevalent palladium catalyst, Pd(PPh3)4, a quantitative cross-coupling of various H-phosphonate diesters with aryl and vinyl halides was achieved in less than 10 min. The reactions occurred with retention of configuration at the phosphorus center and in the vinyl moiety. Using this protocol, several C-phosphonates, including those bearing nucleoside and cholesteryl moieties

  开发了一种微波辅助CP键形成的通用有效方法。使用一种流行的钯催化剂Pd（PPh3）4，在不到10分钟的时间内即可实现各种H-膦酸酯二酯与芳基卤化物和乙烯基卤化物的定量交叉偶联。在磷中心和乙烯基部分保留构型的情况下发生反应。使用该方案，可以高收率制备数种C-膦酸酯，包括带有核苷和胆固醇基部分的C-膦酸酯。
• Ar–P bond construction by the Pd-catalyzed oxidative cross-coupling of arylsilanes with H-phosphonates via C–Si bond cleavage
  作者：Haiqing Luo、Haidong Liu、Xingwei Chen、Keke Wang、Xuzhong Luo、Kejun Wang

  DOI：10.1039/c6cc08408g

  日期：——

  A novel and efficient methodology that allows for the construction of Ar–P bonds via the Pd-catalyzed oxidative cross-coupling reaction of various arylsilanes with H-phosphonates leading to valuable arylphosphonates has been developed.

  通过钯催化各种芳基硅烷与 H-膦酸盐的氧化交叉偶联反应来构建 Ar-P 键，从而制备出有价值的芳基膦酸盐，这是一种新颖而高效的方法。