methyl 5-<(tert-butoxycarbonyl)amino>-2-methoxybenzoate | 180690-86-2

• 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: methyl 5-<(tert-butoxycarbonyl)amino>-2-methoxybenzoate
• 英文别名: methyl 5-((tert-butoxycarbonyl)amino)-2-methoxybenzoate；methyl 2-methoxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate
• CAS: 180690-86-2
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: PLTOMLJZVKLKIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-<(tert-butoxycarbonyl)amino>-2-methoxybenzoate 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 5-{[1-(2,5-Dihydroxy-phenyl)-meth-(E)-ylidene]-amino}-2-methoxy-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis and structure-activity studies of a series of [(hydroxybenzyl)amino]salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity

  摘要：

  The synthesis and structure-activity relationships of a series of [(hydroxybenzylidene)amino] salicylates and a series of [(hydroxybenzyl)amino] salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity are described. Their inhibitory potency was evaluated in vitro using ER 22 cell membranes (CCL 39 cells transfected with EGF receptor) as an enzyme source and the tridecapeptide RRSrc (RRLIEDAEYAARG) as substrate. Their cellular activity was measured by inhibition of the EGF-stimulated DNA synthesis of ER 22 cells. Chemical modifications were made to analyze the role of the different substituents. The amino series was found to be more active than the imino series. The hydroquinone moiety appears to be essential for tyrosine kinase inhibitory activity in the series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Comparison of the imino and amino series by molecular modeling techniques provides further evidence in support of the hypothesis that the important reduced linking chain, CH2NH, allows the correct positioning of the 2,5-dihydroxybenzyl ring, possibly in a cis-like conformational arrangement.

  DOI：

  10.1021/jm00077a014
• 作为产物：
  描述：

  3-(N-叔丁氧羰基氨基)苯甲酸 、 硫酸二甲酯 在 phase-transfer catalyst 作用下， 生成 methyl 5-<(tert-butoxycarbonyl)amino>-2-methoxybenzoate
  参考文献：
  名称：

  Synthesis and structure-activity studies of a series of [(hydroxybenzyl)amino]salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity

  摘要：

  The synthesis and structure-activity relationships of a series of [(hydroxybenzylidene)amino] salicylates and a series of [(hydroxybenzyl)amino] salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity are described. Their inhibitory potency was evaluated in vitro using ER 22 cell membranes (CCL 39 cells transfected with EGF receptor) as an enzyme source and the tridecapeptide RRSrc (RRLIEDAEYAARG) as substrate. Their cellular activity was measured by inhibition of the EGF-stimulated DNA synthesis of ER 22 cells. Chemical modifications were made to analyze the role of the different substituents. The amino series was found to be more active than the imino series. The hydroquinone moiety appears to be essential for tyrosine kinase inhibitory activity in the series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Comparison of the imino and amino series by molecular modeling techniques provides further evidence in support of the hypothesis that the important reduced linking chain, CH2NH, allows the correct positioning of the 2,5-dihydroxybenzyl ring, possibly in a cis-like conformational arrangement.

  DOI：

  10.1021/jm00077a014

文献信息

• Metal-Free Synthesis of Fluorinated Indoles Enabled by Oxidative Dearomatization
  作者：Edon Vitaku、David T. Smith、Jon T. Njardarson

  DOI：10.1002/anie.201511149

  日期：2016.2.5

  fluorinated drugs is increasing each decade. Therefore, new approaches for accessing fluorinated nitrogen heterocycles are of great significance. A novel, scalable, and metal‐free method for accessing a wide range of fluorinated indoles is described. This oxidative‐dearomatization‐enabled approach assembles 2‐trifluoromethyl NH‐indole products from simple commercially available anilines with hexafluoroacetylacetone

  大多数批准的小分子药物中都存在氮杂环，并且批准的氟化药物的数量每十年增加一次。因此，获得氟化氮杂环的新方法具有重要意义。本文介绍了一种新颖，可扩展且不含金属的方法，可用于获得各种氟化吲哚。这种氧化脱芳香化方法可在有机氧化剂存在下，将简单的市售苯胺中的2-三氟甲基NH-吲哚产物与六氟乙酰丙酮组装在一起。苯胺氮封端基团的性质对于这一新反应的成功至关重要。此外，吲哚产物包含3-三氟乙酰基，可利用该基团获得大量有用的官能团。
• Optional Site Selectivity in the Metalation of <i>o</i>- and <i>p</i>-Anisidine through Matching of Reagents with Neighboring Groups
  作者：Raimondo Maggi、Manfred Schlosser

  DOI：10.1021/jo9604550

  日期：1996.1.1

  N-Protected o- and p-anisidines (2- and 4-methoxyanilines) undergo a hydrogen/metal exchange at the position adjacent to either the oxygen or nitrogen atom depending on what organometalic base is employed. These synthetically useful findings support previous views about neighboring group/reagent interactions.
• Synthesis and structure-activity studies of a series of [(hydroxybenzyl)amino]salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity
  作者：Huixiong Chen、Janine Boiziau、Fabienne Parker、Rachid Maroun、Bruno Tocque、Bernard P. Roques、Christiane Garbay-Jaureguiberry

  DOI：10.1021/jm00077a014

  日期：1993.12

  The synthesis and structure-activity relationships of a series of [(hydroxybenzylidene)amino] salicylates and a series of [(hydroxybenzyl)amino] salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity are described. Their inhibitory potency was evaluated in vitro using ER 22 cell membranes (CCL 39 cells transfected with EGF receptor) as an enzyme source and the tridecapeptide RRSrc (RRLIEDAEYAARG) as substrate. Their cellular activity was measured by inhibition of the EGF-stimulated DNA synthesis of ER 22 cells. Chemical modifications were made to analyze the role of the different substituents. The amino series was found to be more active than the imino series. The hydroquinone moiety appears to be essential for tyrosine kinase inhibitory activity in the series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Comparison of the imino and amino series by molecular modeling techniques provides further evidence in support of the hypothesis that the important reduced linking chain, CH2NH, allows the correct positioning of the 2,5-dihydroxybenzyl ring, possibly in a cis-like conformational arrangement.