3-(N-(benzyloxycarbonyl)amino)-3-((2-methyl-ethoxypropionyl)hydroxyphosphinyl) butanoic acid | 260390-97-4

• 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: 3-(N-(benzyloxycarbonyl)amino)-3-((2-methyl-ethoxypropionyl)hydroxyphosphinyl) butanoic acid
• CAS: 260390-97-4
• 化学式: C₁₈H₂₆NO₈P
• 分子量: 415.38
• InChiKey: PZFIZAXHKZRFQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139.23
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(N-(benzyloxycarbonyl)amino)-3-((2-methyl-ethoxypropionyl)hydroxyphosphinyl) butanoic acid 在 palladium on activated charcoal sodium hydroxide 、 ammonium formate 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.2h， 生成 4-[(Adamantan-1-yloxy)-(2-carboxy-propyl)-phosphinoyl]-4-amino-butyric acid adamantan-1-yl ester
  参考文献：
  名称：

  A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon

  摘要：

  Many attempts to synthesize Asp Psi(PO2CH2)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achieved starting from a protected Phe Psi(PO2CH2)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00910-2
• 作为产物：
  描述：

  2-methyl-3((1-(N-(tert-butyloxycarbonyl)amino)-3-phenylpropyl)-hydroxyphosphinyl) propanoic acid, ethyl ester 在 ruthenium trichloride sodium periodate 、 magnesium oxide 、 三氟乙酸 、 silver(l) oxide 作用下， 以 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 10.0h， 生成 3-(N-(benzyloxycarbonyl)amino)-3-((2-methyl-ethoxypropionyl)hydroxyphosphinyl) butanoic acid
  参考文献：
  名称：

  A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon

  摘要：

  Many attempts to synthesize Asp Psi(PO2CH2)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achieved starting from a protected Phe Psi(PO2CH2)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00910-2