allyl 4-(((2-hydroxyethyl)thio)(2-phenylacetamido)methyl)benzoate | 1020296-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: allyl 4-(((2-hydroxyethyl)thio)(2-phenylacetamido)methyl)benzoate
• CAS: 1020296-30-3
• 化学式: C₂₁H₂₃NO₄S
• 分子量: 385.484
• InChiKey: FYUQCSCMPIBXCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 allyl 4-(((2-hydroxyethyl)thio)(2-phenylacetamido)methyl)benzoate 在 三乙胺 作用下， 以 乙腈 为溶剂， 以56%的产率得到allyl 4-(((2-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)ethyl)thio)(2-phenylacetamido)methyl)benzoate
  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：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到allyl 4-(((2-hydroxyethyl)thio)(2-phenylacetamido)methyl)benzoate
  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