7-(3-hydroxy-1-propyl)-6-benzyloxy-4,4,5,6-tetramethylhydrocoumarin | 249589-30-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 7-(3-hydroxy-1-propyl)-6-benzyloxy-4,4,5,6-tetramethylhydrocoumarin
• 英文别名: 7-(3-hydroxypropyl)-4,4,5,8-tetramethyl-6-phenylmethoxy-3H-chromen-2-one
• CAS: 249589-30-8
• 化学式: C₂₃H₂₈O₄
• 分子量: 368.473
• InChiKey: HDOJVZWSBFVQRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(3-hydroxy-1-propyl)-6-benzyloxy-4,4,5,6-tetramethylhydrocoumarin 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到3-[7-(6-benzyloxy-4,4,5,6-tetramethylhydro)coumarinyl]propanal
  参考文献：
  名称：

  A Novel Resin Linker for Solid-Phase Peptide Synthesis Which Can Be Cleaved Using Two Sequential Mild Reactions

  摘要：

  The interest in developing new linkers for solid-phase peptide and organic synthesis has increased tremendously as a result of the rapid development of combinatorial chemistry. Herein, we report the development of a new redox-sensitive linker for solid-phase peptide synthesis. This linker can be readily cleaved under mild conditions by using two sequential mild reactions, a reduction followed by a base (Bu4N+F-)-catalyzed cyclic ether formation. By using this new linker, two short peptides, a tetrapeptide [Boc-Trp-Ala-Gly-Gly-OH] and a pentapeptide [Boc-Asn-Ala-Ser(OBn)-Gly-Glu(OBn)-OH)], were synthesized. Because the cleavage does not use acidic conditions, this resin linker provides an alternative when acidic conditions are not desirable. Furthermore, the cleavage conditions do not affect most of the side chain protecting group. Therefore, the peptides synthesized can be used for the segment synthesis of larger peptides without the need to reprotect the side chain functional groups.

  DOI：

  10.1021/jo990770x
• 作为产物：
  描述：

  7-allyl-6-hydroxy-4,4,5,8-tetramethylhydrocoumarin 在 硼烷 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 22.33h， 生成 7-(3-hydroxy-1-propyl)-6-benzyloxy-4,4,5,6-tetramethylhydrocoumarin
  参考文献：
  名称：

  A Novel Resin Linker for Solid-Phase Peptide Synthesis Which Can Be Cleaved Using Two Sequential Mild Reactions

  摘要：

  The interest in developing new linkers for solid-phase peptide and organic synthesis has increased tremendously as a result of the rapid development of combinatorial chemistry. Herein, we report the development of a new redox-sensitive linker for solid-phase peptide synthesis. This linker can be readily cleaved under mild conditions by using two sequential mild reactions, a reduction followed by a base (Bu4N+F-)-catalyzed cyclic ether formation. By using this new linker, two short peptides, a tetrapeptide [Boc-Trp-Ala-Gly-Gly-OH] and a pentapeptide [Boc-Asn-Ala-Ser(OBn)-Gly-Glu(OBn)-OH)], were synthesized. Because the cleavage does not use acidic conditions, this resin linker provides an alternative when acidic conditions are not desirable. Furthermore, the cleavage conditions do not affect most of the side chain protecting group. Therefore, the peptides synthesized can be used for the segment synthesis of larger peptides without the need to reprotect the side chain functional groups.

  DOI：

  10.1021/jo990770x