2-[[Chloro(methyl)phosphoryl]methyl]isoindole-1,3-dione | 154370-38-4

• 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-[[Chloro(methyl)phosphoryl]methyl]isoindole-1,3-dione
• CAS: 154370-38-4
• 化学式: C₁₀H₉ClNO₃P
• 分子量: 257.613
• InChiKey: WEJIXIFNUSBAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-proline methylamide 、 2-[[Chloro(methyl)phosphoryl]methyl]isoindole-1,3-dione 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到N-<(N-phthaloylaminomethyl)methyl>phosphinoyl-proline-methylamide
  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：

  trimethylsilyl ((1,3-dioxoisoindolin-2-yl)methyl)(methyl)phosphinate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-[[Chloro(methyl)phosphoryl]methyl]isoindole-1,3-dione
  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

文献信息

• 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.