9-fluorenylmethoxycarbonyl chloride | 103559-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-fluorenylmethoxycarbonyl chloride
• 英文别名: 2-(9H-fluoren-9-yloxy)acetyl chloride
• CAS: 103559-40-6
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: FZAKQRYXZCKGCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-fluorenylmethoxycarbonyl chloride 、 L-羟基脯氨酸 在 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 生成 trans-4-hydroxy-N-9-fluorenylmethoxycarbonyl-L-proline
  参考文献：
  名称：

  Solid-Phase Synthesis and Spectroscopic Studies of TRH Analogues Incorporating cis- and trans-4-Hydroxy-L-Proline.

  摘要：

  An efficient solid-phase synthesis of the TRH analogue Glp-His(N(im)-Trt)-Hyp-OH is described. N-alpha-Fmoc protected amino acids and DCC/HOBt activation were employed. The bulky and mild-acid-sensitive 2-chlorotrityl resin, utilised as the solid support, completely suppressed dioxopiperazine formation. The tripeptide is a key intermediate in the synthesis of TRH analogues incorporating cis- and trans-4-hydroxy-L-proline. The tripeptide was converted, with inversion of configuration at C-4 of the Hyp residue, to Glp-His(N(im)-Trt)-cHyp lactone in the presence of triphenylphosphine-diethyl azodicarboxylate (TPP-DEAD). One-pot MeOH-TPP-DEAD transesterification of the lactone, followed by N(im)-detritylation, provided Glp-His-cHyp-OMe. This ester gave the corresponding amide and acid on ammonolysis and saponification, respectively. A high-field H-1 NMR investigation of Glp-His-cHyp-OH and its diastereomer Glp-His-Hyp-OH, obtained by N(im)-detritylation of the key tripeptide, showed that the configuration at C-4 of the prolyl residues is critical for the determination of the preferred three-dimensional structure of the molecules.

  DOI：

  10.3891/acta.chem.scand.45-1047