1-[4-(tert-butoxycarbonylamino)butanoyl]-4-(1,3-diacetoxypropan-2-yloxy)indoline | 952595-59-4

• 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-[4-(tert-butoxycarbonylamino)butanoyl]-4-(1,3-diacetoxypropan-2-yloxy)indoline
• CAS: 952595-59-4
• 化学式: C₂₄H₃₄N₂O₈
• 分子量: 478.543
• InChiKey: FXWOLUCWXLRFJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  120.47
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-[4-(tert-butoxycarbonylamino)butanoyl]-4-(1,3-diacetoxypropan-2-yloxy)indoline 在 4-二甲氨基吡啶 、 乙酸酐 、 copper(II) nitrate 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 生成 [3-Acetyloxy-2-[[1-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]-7-nitro-2,3-dihydroindol-4-yl]oxy]propyl] acetate
  参考文献：
  名称：

  Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors

  摘要：

  A 7-nitroindolin-1-yl amide of the neuroactive amino acid gamma-aminobutryate (GABA) has been synthesised with two phosphate groups attached to the indoline nucleus at 4-alkoxy substituent. The compound is designed to release GABA on a sub-microsecond time scale in response to flash photolysis with near-UV light. The presence of the high negatively charged substituent shows evidence that interaction of the GABA conjugate with ionotropic GABA receptors is much reduced in comparison with an earlier nitroindoline-GABA compound that had no charged groups on the indoline nucleus. In experiments to develop the eventual synthetic route, an unusual reductive cleavage of a TBDMS ether was observed as a significant side reaction during reduction of an indole to an indoline with NaBH3CN in glacial acetic acid. In the eventual synthetic route, the primary amine of GABA was masked as an azide until the final stage of the synthesis, which overcame significant problems with other forms of amine protection. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.030
• 作为产物：
  描述：

  2-(1H-indol-4-yloxy)propane-1,3-diol 在 吡啶 、 sodium cyanoborohydride 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 1-[4-(tert-butoxycarbonylamino)butanoyl]-4-(1,3-diacetoxypropan-2-yloxy)indoline
  参考文献：
  名称：

  Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors

  摘要：

  A 7-nitroindolin-1-yl amide of the neuroactive amino acid gamma-aminobutryate (GABA) has been synthesised with two phosphate groups attached to the indoline nucleus at 4-alkoxy substituent. The compound is designed to release GABA on a sub-microsecond time scale in response to flash photolysis with near-UV light. The presence of the high negatively charged substituent shows evidence that interaction of the GABA conjugate with ionotropic GABA receptors is much reduced in comparison with an earlier nitroindoline-GABA compound that had no charged groups on the indoline nucleus. In experiments to develop the eventual synthetic route, an unusual reductive cleavage of a TBDMS ether was observed as a significant side reaction during reduction of an indole to an indoline with NaBH3CN in glacial acetic acid. In the eventual synthetic route, the primary amine of GABA was masked as an azide until the final stage of the synthesis, which overcame significant problems with other forms of amine protection. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.030