(S)-2-(9-fluorenylmethyloxy)-4-isopropyl-5(4H)-oxazolone | 91613-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-(9-fluorenylmethyloxy)-4-isopropyl-5(4H)-oxazolone
• 英文别名: 2-<(9-fluorenylmethyl)oxy>-4-isopropyl-5(4H)-oxazolone；2-(9H-fluoren-9-ylmethoxy)-4-propan-2-yl-4H-1,3-oxazol-5-one
• CAS: 91613-96-6
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: NREBLFTUSXUZFH-UHFFFAOYSA-N

物化性质

• 沸点：
  443.5±38.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(9-fluorenylmethyloxy)-4-isopropyl-5(4H)-oxazolone 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 9-亚甲基芴
  参考文献：
  名称：

  Paquet, Alenka; Chen, Francis M. F.; Benoiton, N. Leo, Canadian Journal of Chemistry, 1984, vol. 62, p. 1335 - 1338

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(9H-芴-9-基)甲基(1-氯-3-甲基-1-氧代-2-丁基)氨基甲酸酯 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以62.3%的产率得到(S)-2-(9-fluorenylmethyloxy)-4-isopropyl-5(4H)-oxazolone
  参考文献：
  名称：

  [(9-Fluorenylmethyl)oxy]carbonyl (Fmoc) amino acid chlorides in solid-phase peptide synthesis

  摘要：

  FMOC amino acid chlorides, previously shown to be rapid-acting coupling agents in two-phase systems or in homogeneous solution, did not prove to be directly applicable to solid-phase peptide synthesis due to sluggish reactivity. The problem was traced to prior conversion of the acid chlorides by necessary basic co-reactants (DIEA, NMM, etc.) to the corresponding oxazolones. If, in their place, 1:1 mixtures of these bases and HOBt were used, rapid solid-phase acylations were possible via the intermediate formation of the corresponding HOBt esters. The 1:1 base-HOBt mixtures also were shown to enhance generally the reactivity of FMOC amino acid active esters over that caused by HOBt alone. Peptides assembled from acid chlorides by using these techniques included leucine enkephalin, the ACP decapeptide (65-74), prothrombin (1-9), several substance P analogues, and eledoisin. Where particular acid chlorides could not be used due to their instability, the corresponding pentafluorophenyl esters or mixtures of the acids and BOP reagent were used.

  DOI：

  10.1021/jo00008a012

文献信息

• CARPINO, LOUIS A.;CHAO, HANN GUANG;BEYERMANN, MICHAEL;BIENERT, MICHAEL, J. ORG. CHEM., 56,(1991) N, C. 2635-2642
  作者：CARPINO, LOUIS A.、CHAO, HANN GUANG、BEYERMANN, MICHAEL、BIENERT, MICHAEL

  DOI：——

  日期：——