4-[[[2-[[[(2-Oxo-2H-1-benzopyran-7-yl)oxy]carbonyl]oxy]ethyl]thio][(2-phenylacetyl)amino]methyl]benzoic acid | 1020295-93-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-[[[2-[[[(2-Oxo-2H-1-benzopyran-7-yl)oxy]carbonyl]oxy]ethyl]thio][(2-phenylacetyl)amino]methyl]benzoic acid
• 英文别名: 4-[2-(2-oxochromen-7-yl)oxycarbonyloxyethylsulfanyl-[(2-phenylacetyl)amino]methyl]benzoic acid
• CAS: 1020295-93-5
• 化学式: C₂₈H₂₃NO₈S
• 分子量: 533.559
• InChiKey: XFYCURBOGMUZEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[[[2-[[[(2-Oxo-2H-1-benzopyran-7-yl)oxy]carbonyl]oxy]ethyl]thio][(2-phenylacetyl)amino]methyl]benzoic acid 反应 0.5h， 生成 7-羟基香豆素
  参考文献：
  名称：

  Development of a New Nonpeptidic Self-Immolative Spacer. Application to the Design of Protease Sensing Fluorogenic Probes

  摘要：

  The design and synthesis of novel self-immolative spacer systems aiming at the release of phenol-containing compounds are described. The newly designed traceless linkers proved to be conveniently stable under physiological conditions and operate through spontaneous decomposition of an hemithioaminal intermediate under neutral aqueous conditions. Their utility was then illustrated by the preparation of original fluorogenic substrates of penicillin amidase whose strong fluorescence is unveiled through enzyme-initiated domino reactions.

  DOI：

  10.1021/ol800198f
• 作为产物：
  描述：

  C₃₁H₂₇NO₈S 在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 、 苄胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.17h， 以33%的产率得到4-[[[2-[[[(2-Oxo-2H-1-benzopyran-7-yl)oxy]carbonyl]oxy]ethyl]thio][(2-phenylacetyl)amino]methyl]benzoic acid
  参考文献：
  名称：

  Development of a New Nonpeptidic Self-Immolative Spacer. Application to the Design of Protease Sensing Fluorogenic Probes

  摘要：

  The design and synthesis of novel self-immolative spacer systems aiming at the release of phenol-containing compounds are described. The newly designed traceless linkers proved to be conveniently stable under physiological conditions and operate through spontaneous decomposition of an hemithioaminal intermediate under neutral aqueous conditions. Their utility was then illustrated by the preparation of original fluorogenic substrates of penicillin amidase whose strong fluorescence is unveiled through enzyme-initiated domino reactions.

  DOI：

  10.1021/ol800198f

文献信息

• Development of a New Nonpeptidic Self-Immolative Spacer. Application to the Design of Protease Sensing Fluorogenic Probes
  作者：Yves Meyer、Jean-Alexandre Richard、Marc Massonneau、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1021/ol800198f

  日期：2008.4.1

  The design and synthesis of novel self-immolative spacer systems aiming at the release of phenol-containing compounds are described. The newly designed traceless linkers proved to be conveniently stable under physiological conditions and operate through spontaneous decomposition of an hemithioaminal intermediate under neutral aqueous conditions. Their utility was then illustrated by the preparation of original fluorogenic substrates of penicillin amidase whose strong fluorescence is unveiled through enzyme-initiated domino reactions.