(2-methyldiphenyl)methylphosphonic acid diethyl ester | 176713-79-4

• 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: (2-methyldiphenyl)methylphosphonic acid diethyl ester
• 英文别名: 1-[Diethoxyphosphoryl(phenyl)methyl]-2-methylbenzene；1-[diethoxyphosphoryl(phenyl)methyl]-2-methylbenzene
• CAS: 176713-79-4
• 化学式: C₁₈H₂₃O₃P
• 分子量: 318.353
• InChiKey: GWSMGWCYKVRHSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• 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：

  (2-methyldiphenyl)methylphosphonic acid diethyl ester 生成 (Phenyl-o-tolyl-methyl)-phosphonic acid
  参考文献：
  名称：

  Benzylphosphonic acid inhibitors of human prostatic acid phosphatase

  摘要：

  A series of alpha-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme which has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 mu M), and alpha-(2-phenylethyl)benzylphosphonic acid (14 mu M) The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through alpha-carbon substitution.

  DOI：

  10.1016/0960-894x(96)00018-2
• 作为产物：
  描述：

  2-甲基二苯甲酮 在 三溴化磷 作用下， 生成 (2-methyldiphenyl)methylphosphonic acid diethyl ester
  参考文献：
  名称：

  Benzylphosphonic acid inhibitors of human prostatic acid phosphatase

  摘要：

  A series of alpha-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme which has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 mu M), and alpha-(2-phenylethyl)benzylphosphonic acid (14 mu M) The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through alpha-carbon substitution.

  DOI：

  10.1016/0960-894x(96)00018-2

文献信息

• 大位阻烷基取代亚膦酸二酯的制备方法
  申请人：温州大学

  公开号：CN110922427B

  公开（公告）日：2022-07-15

  本发明公开了一种大位阻烷基取代亚膦酸二酯的制备方法，本发明使用三氟甲磺酸三甲基硅酯为催化剂，实现大位阻醇类与亚磷酸三酯的直接反应制备已知方法很难合成的大位阻烷基取代亚膦酸二酯类化合物的新方法。因此，本方法可以说是对阿尔布佐夫方法合成大位阻烷基取代亚膦酸二酯类化合物的突破，由于本方法还适用于一般的伯醇原料，因此是一种具有高普适性的改进阿尔布佐夫方法。具体地，本方法使用稳定低毒的大位阻醇类为原料，反应条件简单、易于操作、无需溶剂，催化剂不含过渡金属，产物无过渡金属残留隐患，副产物为小分子的醇类如乙醇，几乎无毒性，因此是一种大位阻烷基取代亚膦酸二酯的绿色合成方法，具有很好研究价值和合成应用前景。
• Highly Effective Alkaline Earth Catalysts for the Sterically Governed Hydrophosphonylation of Aldehydes and Nonactivated Ketones
  作者：Bo Liu、Jean-François Carpentier、Yann Sarazin

  DOI：10.1002/chem.201201489

  日期：2012.10.15

  Down‐to‐earth catalysis: Heteroleptic and, more interestingly, homoleptic complexes of the large alkaline earth metals (calcium, strontium, and barium) constitute remarkably efficient catalysts for hydrophosphonylation reactions of aldehydes and nonactivated ketones (see scheme). Perfect chemoselectivities and unprecedented turnover frequencies (TOFs) are reported.

  脚踏实地的催化作用：大型碱土金属（钙，锶和钡）的杂合剂，更有趣的是，均合的配合物构成了醛和未活化酮的氢膦酰化反应的高效催化剂（参见方案）。完美的化学选择性和空前的周转频率（TOFs）报道。
• Benzylphosphonic acid inhibitors of human prostatic acid phosphatase
  作者：Charles F. Schwender、Scott A. Beers、Elizabeth A. Malloy、Jacqueline J. Cinicola、David J. Wustrow、Keith D. Demarest、Jerold Jordan

  DOI：10.1016/0960-894x(96)00018-2

  日期：1996.2

  A series of alpha-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme which has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 mu M), and alpha-(2-phenylethyl)benzylphosphonic acid (14 mu M) The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through alpha-carbon substitution.