diethyl 2-(indol-4-yloxy)malonate | 868947-76-6

• 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: diethyl 2-(indol-4-yloxy)malonate
• 英文别名: diethyl 2-(1H-indol-4-yloxy)propanedioate
• CAS: 868947-76-6
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: DXCNQXWUOLNHNI-UHFFFAOYSA-N

物化性质

• 沸点：
  433.4±30.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(indol-4-yloxy)malonate 在 咪唑 、 lithium aluminium tetrahydride 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-[1,3-di(tert-butyldimethylsilyloxy)propan-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
• 作为产物：
  描述：

  benzyl 4-(tert-butyldimethylsilyloxy)indole-1-carboxylate 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 18.92h， 生成 diethyl 2-(indol-4-yloxy)malonate
  参考文献：
  名称：

  避免通过溴代丙二酸二乙酯使4-羟基吲哚的O-烷基异常烷基化的策略

  摘要：

  在标准条件下，用溴代丙二酸二乙酯（碳酸钾-丙酮）将4-羟基吲哚烷基化，得到预期的吲哚基氧基丙二酸酯3和异常的吲哚基氧基-2-溴-丙二酸酯4。取决于条件，两种产物的比例在4：1和1：2之间变化。通过碳苄氧基保护吲哚氮消除了异常产物的形成。

  DOI：

  10.1002/jhet.5570420610

文献信息

• Anionically substituted 7-nitroindoline derivatives and their uses
  申请人：Corrie John

  公开号：US20070203099A1

  公开（公告）日：2007-08-30

  Anionically substituted 7-nitroindoline derivatives are disclosed and their uses as caged compounds from which effector species such as neurotransmitters and amino acids are releasable on irradiation with light.

  本文披露了阴离子取代的7-硝基吲哚衍生物，它们可作为光释放的笼状化合物，从中释放出神经递质和氨基酸等效应物质。
• Anionically substituted 7-Nitroindoline derivatives and their uses
  申请人：Medical Research Council

  公开号：EP1757585B1

  公开（公告）日：2010-12-01
• US7737169B2
  申请人：——

  公开号：US7737169B2

  公开（公告）日：2010-06-15
• A strategy to avoid anomalous<i>O</i>-alkylation of 4-hydroxyindole by diethyl bromomalonate
  作者：George Papageorgiou、John E. T. Corrie

  DOI：10.1002/jhet.5570420610

  日期：2005.9

  Alkylation of 4-hydroxyindole with diethyl bromomalonate under standard conditions (potassium carbonate-acetone) gave the expected indolyloxymalonate ester 3 together with the anomalous indolyloxy-2-bro-momalonate 4. Depending on conditions, the ratio of the two products varied between 4:1 and 1:2. Protection of the indole nitrogen by a carbobenzyloxy group eliminated formation of the anomalous product

  在标准条件下，用溴代丙二酸二乙酯（碳酸钾-丙酮）将4-羟基吲哚烷基化，得到预期的吲哚基氧基丙二酸酯3和异常的吲哚基氧基-2-溴-丙二酸酯4。取决于条件，两种产物的比例在4：1和1：2之间变化。通过碳苄氧基保护吲哚氮消除了异常产物的形成。
• Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors
  作者：George Papageorgiou、John E.T. Corrie

  DOI：10.1016/j.tet.2007.07.030

  日期：2007.9

  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.