1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol | 690629-94-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol
• CAS: 690629-94-8
• 化学式: C₂₇H₄₅NO₅Si
• 分子量: 491.744
• InChiKey: CSQMXOFXFWHDIE-OTDUKCBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 以99%的产率得到1-O-(N-Boc-D-leucyl)-2-[(Z)-3-hydroxy-1-propenyl]-4-methylphenol
  参考文献：
  名称：

  The effect of substitution patterns on the release rates of opioid peptides DADLE and [Leu5]-enkephalin from coumarin prodrug moieties

  摘要：

  A coumarin-based prodrug system has been developed in our laboratory for the preparation of esterase-sensitive prodrugs of amines, peptides, and peptidomimetics. The drug release rates from this prodrug system were found to be dependent on the structural features of the drug moiety. The effect of the phenyl ring substitutions on the release kinetics of such prodrugs of model amines was examined recently and it was found that appropriately positioned alkyl substituents on the phenyl ring could help to facilitate the release. Aimed at further understanding the structure-release rate relationship of the coumarin-based cyclic prodrugs, we synthesized and examined a series of substituted coumarinic acid derivatives of opioid peptides, DADLE, and [Leu(5)]-enkephalin. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.12.002
• 作为产物：
  描述：

  6-甲基香豆素 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol
  参考文献：
  名称：

  The effect of substitution patterns on the release rates of opioid peptides DADLE and [Leu5]-enkephalin from coumarin prodrug moieties

  摘要：

  A coumarin-based prodrug system has been developed in our laboratory for the preparation of esterase-sensitive prodrugs of amines, peptides, and peptidomimetics. The drug release rates from this prodrug system were found to be dependent on the structural features of the drug moiety. The effect of the phenyl ring substitutions on the release kinetics of such prodrugs of model amines was examined recently and it was found that appropriately positioned alkyl substituents on the phenyl ring could help to facilitate the release. Aimed at further understanding the structure-release rate relationship of the coumarin-based cyclic prodrugs, we synthesized and examined a series of substituted coumarinic acid derivatives of opioid peptides, DADLE, and [Leu(5)]-enkephalin. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.12.002