diethyl <(4-chlorophenyl) phenylmethyl> phosphonate | 76194-47-3

• 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: diethyl <(4-chlorophenyl) phenylmethyl> phosphonate
• 英文别名: (4-chlorodiphenyl)methylphosphonic acid diethyl ester；1-Chloro-4-[diethoxyphosphoryl(phenyl)methyl]benzene
• CAS: 76194-47-3
• 化学式: C₁₇H₂₀ClO₃P
• 分子量: 338.771
• InChiKey: DKTABKDZRQVNRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  diethyl <(4-chlorophenyl) phenylmethyl> phosphonate 生成 4-Chlor-diphenyl-methyl-phosphonsaeure
  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：

  4-氯二苯甲醇 在 三溴化磷 作用下， 生成 diethyl <(4-chlorophenyl) phenylmethyl> phosphonate
  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。
• Lewis-acid-catalyzed phosphorylation of alcohols
  作者：Xiao-Hong Wang、Xuan Liu、Ya-Wen Xue、Yan-Bin Wang、Xiao-Hong Wei、Qiong Su

  DOI：10.1039/d3ra08214h

  日期：——

  has been developed for reacting dialkyl H-phosphonates or diarylphosphine oxides with alcohols for constructing C–P bonds. This reaction was catalyzed by Lewis acid and involved nucleophilic substitution. A series of diphenylphosphonates and diphenylphosphine oxides were obtained, from the phosphorylation of alcohols, with good-to-excellent yields.

  已经开发了一种将二烷基 H-膦酸盐或二芳基膦氧化物与醇反应以构建 C-P 键的有效方法。该反应由 Lewis acid 催化并涉及亲核取代。从醇的磷酸化中获得一系列二苯基膦酸盐和二苯基膦氧化物，产率从好到极好。
• 一种酸催化合成二芳基膦酸酯类衍生物的方法
  申请人：西北民族大学

  公开号：CN115651014A

  公开（公告）日：2023-01-31

  本发明一种酸催化合成二芳基膦酸酯类衍生物的方法采用有机磷为磷酰化试剂，路易斯酸为催化剂，通式I所示的二芳基醇和通式 所示的有机磷通过磷酰化反应一步构建C‑P键，合成二芳基膦酸酯类衍生物。其中，通式I所示的二芳基醇、通式II所示的有机磷的投料摩尔比为1∶1~1∶3，通式I所示的二芳基醇和路易斯酸催化剂的投料摩尔比为100∶0~100∶20；通式I所示的二芳基醇和布朗斯特酸的投料摩尔比1∶1~1∶3。与现有方法相比，本发明具有反应条件温和、原料廉价易得、底物适用范围广、原子经济性高、环境友好、步骤经济性等特点。
• Synthesis and pharmacological study of new calcium antagonists, analogues of cinnarizine and flunarizine
  作者：S Younes、G Baziard-Mouysset、G de Saqui-Sannes、JL Stigliani、M Payard、R Bonnafous、J Tisne-Versailles

  DOI：10.1016/0223-5234(93)90049-k

  日期：1993.1

  Several phosphonic diethyl esters were synthesized and their calcium antagonistic activity evaluated in vitro. The diethyl phosphonate group was condensed on substituted [diphenylmethyl], [(2-benzofuranyl)phenylmethyl], [(4-(diphenylmethyl-1 piperazinyl) methyl], [4-(4-diphenylmethyl-1-piperazinyl methyl) phenylmethyl], and [4-(3-phenyl-2-propenyl)-1-piperazinyl methyl] groups. Despite the presence of the diethyl phosphonate moiety and the benzhydrylpiperazinyl group, both present in potent calcium antagonist structures, only 1 of the 19 synthesized compounds exhibited a calcium antagonistic profile.
• 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.