(2-phenylethyl)[2-(phthalimido)ethyl]phosphinic acid | 500105-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2-phenylethyl)[2-(phthalimido)ethyl]phosphinic acid
• 英文别名: [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl](2-phenylethyl)phosphinic acid；2-(1,3-dioxoisoindol-2-yl)ethyl-(2-phenylethyl)phosphinic acid
• CAS: 500105-04-4
• 化学式: C₁₈H₁₈NO₄P
• 分子量: 343.319
• InChiKey: RLMUQEUGCVFEIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-phenylethyl)[2-(phthalimido)ethyl]phosphinic acid 在 盐酸 、 水 作用下， 反应 15.0h， 以83%的产率得到(2-aminoethyl)(2-phenylethyl)phosphinic acid hydrochloride
  参考文献：
  名称：

  A method of synthesis of phosphinic acids on the basis of hypophosphites: VII. Synthesis of pseudo-γ-aminobutanoyl peptides and other phosphinic analogs of γ-aminobutyric acid

  摘要：

  A method of synthesis of pseudo-gamma-aminobutanoyl peptides and other phosphinic analogs of gamma-aminobutyric acid from hypophosphites is suggested. Silyl phosphonites formed by in situ addition of bis-(trimethylsilyl) hypophosphite to the corresponding alpha-substituted acrylates, styrene, or vinyl phosphonate used as unsaturated components in the synthesis react in situ with N-(omega-bromoalkyl)phthalimides by an Arbuzov reaction scheme, affording omega-(phthalimido)alkylphosphinic acids possessing beta-substituted beta-(alkoxycarbonyl)ethyl, beta-phenylethyl, or beta-(diethoxyphosphinoyl)ethyl substituents. Acid hydrolysis of these reaction products gives the target aminophosphinic acids: phosphinic analogs of gamma-aminobutyric acid.

  DOI：

  10.1134/s107036320809003x
• 作为产物：
  描述：

  N-(2-溴乙基)邻苯二甲酰亚胺 、 bis(trimethylsilyl) (2-phenylethyl)phosphonite 在 乙醇 作用下， 反应 10.5h， 以43%的产率得到(2-phenylethyl)[2-(phthalimido)ethyl]phosphinic acid
  参考文献：
  名称：

  A method of synthesis of phosphinic acids on the basis of hypophosphites: VII. Synthesis of pseudo-γ-aminobutanoyl peptides and other phosphinic analogs of γ-aminobutyric acid

  摘要：

  A method of synthesis of pseudo-gamma-aminobutanoyl peptides and other phosphinic analogs of gamma-aminobutyric acid from hypophosphites is suggested. Silyl phosphonites formed by in situ addition of bis-(trimethylsilyl) hypophosphite to the corresponding alpha-substituted acrylates, styrene, or vinyl phosphonate used as unsaturated components in the synthesis react in situ with N-(omega-bromoalkyl)phthalimides by an Arbuzov reaction scheme, affording omega-(phthalimido)alkylphosphinic acids possessing beta-substituted beta-(alkoxycarbonyl)ethyl, beta-phenylethyl, or beta-(diethoxyphosphinoyl)ethyl substituents. Acid hydrolysis of these reaction products gives the target aminophosphinic acids: phosphinic analogs of gamma-aminobutyric acid.

  DOI：

  10.1134/s107036320809003x

文献信息

• A method of synthesis of phosphinic acids on the basis of hypophosphites: VII. Synthesis of pseudo-γ-aminobutanoyl peptides and other phosphinic analogs of γ-aminobutyric acid
  作者：V. V. Ragulin

  DOI：10.1134/s107036320809003x

  日期：2008.9

  A method of synthesis of pseudo-gamma-aminobutanoyl peptides and other phosphinic analogs of gamma-aminobutyric acid from hypophosphites is suggested. Silyl phosphonites formed by in situ addition of bis-(trimethylsilyl) hypophosphite to the corresponding alpha-substituted acrylates, styrene, or vinyl phosphonate used as unsaturated components in the synthesis react in situ with N-(omega-bromoalkyl)phthalimides by an Arbuzov reaction scheme, affording omega-(phthalimido)alkylphosphinic acids possessing beta-substituted beta-(alkoxycarbonyl)ethyl, beta-phenylethyl, or beta-(diethoxyphosphinoyl)ethyl substituents. Acid hydrolysis of these reaction products gives the target aminophosphinic acids: phosphinic analogs of gamma-aminobutyric acid.