ethyl (phthaloylaminomethyl)methylphosphinate | 4731-73-1

• 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: ethyl (phthaloylaminomethyl)methylphosphinate
• 英文别名: ethyl ((1,3-dioxoisoindolin-2-yl)methyl)(methyl)phosphinate；Ethoxy-methyl-phthalimidomethyl-phosphinoxid；methyl-phthalimidomethyl-phosphinic acid ethyl ester；2-[[Ethoxy(methyl)phosphoryl]methyl]isoindole-1,3-dione
• CAS: 4731-73-1
• 化学式: C₁₂H₁₄NO₄P
• 分子量: 267.221
• InChiKey: JOUUKTWKTAPZML-UHFFFAOYSA-N

物化性质

• 熔点：
  109-111 °C
• 沸点：
  385.8±44.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (phthaloylaminomethyl)methylphosphinate 在 盐酸 作用下， 反应 8.0h， 以96%的产率得到(aminomethyl)(methyl)phosphinic acid
  参考文献：
  名称：

  Peptides containing the novel methylphosphinamide transition-state isostere

  摘要：

  A convenient route towards the synthesis of peptides containing the methylphosphinamide moiety as a novel transition-state isostere of the amide bond hydrolysis is described. The key step being the coupling of a methylphosphinic chloride with an amino acid or peptide protected at the C-terminus. A proper choice of the amino protecting group appeared to be essential.

  DOI：

  10.1016/s0040-4020(01)80258-1
• 作为产物：
  描述：

  N-溴甲基邻苯二甲酰亚胺 、 甲基二乙氧基膦 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 80.0 ℃ 、30.0 kPa 条件下， 反应 2.0h， 以77%的产率得到ethyl (phthaloylaminomethyl)methylphosphinate
  参考文献：
  名称：

  轻松访问具有羧基，酰胺和膦酸酯连接功能的12元大环配体PCTA及其衍生物

  摘要：

  据报道，它是传统的Richman-Atkins方法获得PCTA和新衍生物的一种便捷有效的替代方法。由于钠模板效应，关键的大环化步骤以高收率发生。据报道，衍生自这些新的PCTA配体的镧系元素（III）可能用作顺磁性造影剂或发光体。

  DOI：

  10.1002/ejoc.201800066

文献信息

• NOVEL PYRROLE DERIVATIVES AND THEIR SYNTHESIS
  申请人：PRADHAN Braja SUNDAR

  公开号：US20110263870A1

  公开（公告）日：2011-10-27

  The present invention relates to two novel pyrrole derivatives [3-Phenyl-4-(phenylcarbamoyl)-2-(4-fluorophenyl)-5-(1-methylethyl)-pyrrole-1-yl]methyl(diphenyl)phosphine oxide and Diethyl [3-Phenyl-4-(phenylcarbamoyl)-2-(4-fluorophenyl)-5-(1-methylethyl)-pyrrole-1-yl]methylphosphonate. These pyrrole derivatives can be used as intermediates for the synthesis of the anticholesterol drug atorvastatin.

  该发明涉及两种新颖的吡咯衍生物[3-苯基-4-(苯基氨甲酰)-2-(4-氟苯基)-5-(1-甲基乙基)-吡咯-1-基]甲基(二苯基)膦氧化物和[3-苯基-4-(苯基氨甲酰)-2-(4-氟苯基)-5-(1-甲基乙基)-吡咯-1-基]甲基膦酸二乙酯。这些吡咯衍生物可用作合成抗胆固醇药物阿托伐他汀的中间体。
• Facile Access to the 12-Membered Macrocyclic Ligand PCTA and Its Derivatives with Carboxylate, Amide, and Phosphinate Ligating Functionalities
  作者：Morgane Enel、Nadine Leygue、Nathalie Saffon、Chantal Galaup、Claude Picard

  DOI：10.1002/ejoc.201800066

  日期：2018.4.23

  convenient and efficient alternative to the classical Richman–Atkins methodology for obtaining PCTA and new derivatives is reported. The key macrocyclization step occurs in good yields as a result of a sodium template effect. The potentiality of lanthanide(III) complexes derived from these new PCTA ligands to act as paramagnetic contrastophores or luminophores is reported.

  据报道，它是传统的Richman-Atkins方法获得PCTA和新衍生物的一种便捷有效的替代方法。由于钠模板效应，关键的大环化步骤以高收率发生。据报道，衍生自这些新的PCTA配体的镧系元素（III）可能用作顺磁性造影剂或发光体。
• Peptides containing the novel methylphosphinamide transition-state isostere
  作者：Wilna J. Moree、Gijs A. van der Marel、Jacques H. van Boom、Rob M.J. Liskamp

  DOI：10.1016/s0040-4020(01)80258-1

  日期：1993.1

  A convenient route towards the synthesis of peptides containing the methylphosphinamide moiety as a novel transition-state isostere of the amide bond hydrolysis is described. The key step being the coupling of a methylphosphinic chloride with an amino acid or peptide protected at the C-terminus. A proper choice of the amino protecting group appeared to be essential.