Acetic acid 2-[(tert-butoxycarbonyl-pentyl-amino)-methyl]-4-hydroxymethyl-phenyl ester | 369366-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Acetic acid 2-[(tert-butoxycarbonyl-pentyl-amino)-methyl]-4-hydroxymethyl-phenyl ester
• CAS: 369366-14-3
• 化学式: C₂₀H₃₁NO₅
• 分子量: 365.47
• InChiKey: VQFLCYCNZUFJLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  芴甲氧羰基-DL-丙氨酸 、 Acetic acid 2-[(tert-butoxycarbonyl-pentyl-amino)-methyl]-4-hydroxymethyl-phenyl ester 在 4-二甲氨基吡啶 、 达卡巴嗪 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propionic acid 4-acetoxy-3-[(tert-butoxycarbonyl-pentyl-amino)-methyl]-benzyl ester
  参考文献：
  名称：

  A new bio-compatible pH cleavable linker for solid-phase synthesis of a squalamine analogue

  摘要：

  Linkers that can be cleaved directly within the biological assay offer some advantages over traditional linkers in the range of direct screening applications that the associated libraries can be utilised for. The 1,6-elimination process is an efficient method of cleaning compounds from substituted 4-hydroxymethyl phenols, although giving rise to quinone methide by-products. Here, we report on a linker that uses an in-built amine 'activator' to cleave a phenoxy ester and hence to activate the linker to 1,6-elimination. An analogue of the antibacterial agent squalamine was synthesised and released using this linker strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01217-5
• 作为产物：
  描述：

  5-formyl-2-hydroxy-N-pentylbenzamide 在 sodium hydroxide 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Acetic acid 2-[(tert-butoxycarbonyl-pentyl-amino)-methyl]-4-hydroxymethyl-phenyl ester
  参考文献：
  名称：

  A new bio-compatible pH cleavable linker for solid-phase synthesis of a squalamine analogue

  摘要：

  Linkers that can be cleaved directly within the biological assay offer some advantages over traditional linkers in the range of direct screening applications that the associated libraries can be utilised for. The 1,6-elimination process is an efficient method of cleaning compounds from substituted 4-hydroxymethyl phenols, although giving rise to quinone methide by-products. Here, we report on a linker that uses an in-built amine 'activator' to cleave a phenoxy ester and hence to activate the linker to 1,6-elimination. An analogue of the antibacterial agent squalamine was synthesised and released using this linker strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01217-5