[2-(4-Chloro-phenyl)-1-(diethoxy-phosphoryl)-ethyl]-phosphonic acid diethyl ester | 53235-98-6

• 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: [2-(4-Chloro-phenyl)-1-(diethoxy-phosphoryl)-ethyl]-phosphonic acid diethyl ester
• 英文别名: 1-[2,2-Bis(diethoxyphosphoryl)ethyl]-4-chlorobenzene
• CAS: 53235-98-6
• 化学式: C₁₆H₂₇ClO₆P₂
• 分子量: 412.787
• InChiKey: DPMADDQAHUCVSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-(4-Chloro-phenyl)-1-(diethoxy-phosphoryl)-ethyl]-phosphonic acid diethyl ester 在 盐酸 、 sodium hypochlorite 、 碳酸氢钠 作用下， 反应 19.0h， 生成 [1-Chloro-2-(4-chloro-phenyl)-1-(dimethoxy-phosphoryl)-ethyl]-phosphonic acid dimethyl ester
  参考文献：
  名称：

  gem-Diphosphonate and gem-phosphonate-phosphate compounds with specific high density lipoprotein inducing activity

  摘要：

  New diphosphonate compounds and related derivatives were synthesized and investigated for their activity in specifically inducing plasma high density lipoproteins (HDL) and high density lipoprotein cholesterol (HDL-C) in normal rats. The screening of numerous compounds has permitted the determination of the structural variations leading to optimal plasma lipid altering activity, indicating antiatherosclerotic potential. Among the compounds observed to be the most active, dimethyl alpha-(dimethoxyphosphinyl)-p-chlorobenzyl phosphate (20, SR-202, mifobate) was selected for further pharmacological and subsequent clinical development.

  DOI：

  10.1021/jm00391a027
• 作为产物：
  描述：

  tetraethyl<(p-chlorophenyl)vinylidene>bisphosphonate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 [2-(4-Chloro-phenyl)-1-(diethoxy-phosphoryl)-ethyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  TiCl 4 / base-IV的Knoevenagel kondensationen mit ：醛基酮和酮基酮

  摘要：

  在四氯化钛和有机碱在四氢呋喃中的存在下，三乙基膦酰基乙酸与脂族和芳族醛和芳族酮缩合，分别得到相应的三乙基亚烷基和亚芳基膦酰基乙酸。亚甲基二膦酸四烷基酯与芳族或脂族α-支化醛在相同条件下以相同方式反应。众所周知的三乙基亚烷基和亚芳基膦酰基乙酸以及新的四烷基亚烷基和亚芳基甲烷二膦酸很容易在乙醇中催化或通过硼氢化钠加氢，以几乎定量的产率得到相应的饱和化合物。

  DOI：

  10.1016/s0040-4020(01)91461-9

文献信息

• NGUYEN, LAN M.;NIESOR, ERIC;BENTZEN, CRAIG L., J. MED. CHEM., 30,(1987) N 8, 1426-1433
  作者：NGUYEN, LAN M.、NIESOR, ERIC、BENTZEN, CRAIG L.

  DOI：——

  日期：——
• Knoevenagel kondensationen mit TiCl4/base-IV
  作者：W. Lehnert

  DOI：10.1016/s0040-4020(01)91461-9

  日期：1974.1

  In the presence of titanium tetrachloride and an organic base in tetrahydrofurane, triethyl phosphonoacetic acid undergoes condensation with aliphatic and aromatic aldehydes and aromatic ketones to yield the corresponding triethyl alkylidene and arylidene phosphonoacetic acids respectively. Tetraalkyl methylenediphosphonates and aromatic or aliphatic α-branched aldehydes react under identical conditions

  在四氯化钛和有机碱在四氢呋喃中的存在下，三乙基膦酰基乙酸与脂族和芳族醛和芳族酮缩合，分别得到相应的三乙基亚烷基和亚芳基膦酰基乙酸。亚甲基二膦酸四烷基酯与芳族或脂族α-支化醛在相同条件下以相同方式反应。众所周知的三乙基亚烷基和亚芳基膦酰基乙酸以及新的四烷基亚烷基和亚芳基甲烷二膦酸很容易在乙醇中催化或通过硼氢化钠加氢，以几乎定量的产率得到相应的饱和化合物。
• gem-Diphosphonate and gem-phosphonate-phosphate compounds with specific high density lipoprotein inducing activity
  作者：Nguyen Lan Mong、Eric Niesor、Craig L. Bentzen

  DOI：10.1021/jm00391a027

  日期：1987.8

  New diphosphonate compounds and related derivatives were synthesized and investigated for their activity in specifically inducing plasma high density lipoproteins (HDL) and high density lipoprotein cholesterol (HDL-C) in normal rats. The screening of numerous compounds has permitted the determination of the structural variations leading to optimal plasma lipid altering activity, indicating antiatherosclerotic potential. Among the compounds observed to be the most active, dimethyl alpha-(dimethoxyphosphinyl)-p-chlorobenzyl phosphate (20, SR-202, mifobate) was selected for further pharmacological and subsequent clinical development.