5-{[(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl-methyl]-hydroxy-phosphinoyl}-pentanoic acid | 918950-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5-{[(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl-methyl]-hydroxy-phosphinoyl}-pentanoic acid
• CAS: 918950-51-3
• 化学式: C₂₇H₂₈NO₆P
• 分子量: 493.496
• InChiKey: RLWIRFQBZLUIMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  112.93
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-{[(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl-methyl]-hydroxy-phosphinoyl}-pentanoic acid 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 5-{[(9H-fluoren-9-yl-methoxycarbonylamino)-phenyl-methyl]-hydroxy-phosphinoyl}-pentanoic acid 2-oxo-2-phenyl-ethyl ester
  参考文献：
  名称：

  Chemoselective Protection of Solid-Phase Compatible Fmoc-Phosphinic Building Blocks

  摘要：

  An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).

  DOI：

  10.1021/jo061535z
• 作为产物：
  描述：

  4-戊烯酸 在 次磷酸铵 、 三乙基硼 、 溶剂黄146 、 乙酰氯 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 10.0h， 生成 5-{[(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl-methyl]-hydroxy-phosphinoyl}-pentanoic acid
  参考文献：
  名称：

  Chemoselective Protection of Solid-Phase Compatible Fmoc-Phosphinic Building Blocks

  摘要：

  An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).

  DOI：

  10.1021/jo061535z