methyl 3-(2-formyl-6-methoxyphenoxy)acrylate | 1006104-53-5

• 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 3-(2-formyl-6-methoxyphenoxy)acrylate
• CAS: 1006104-53-5
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: OQYIFRFQQMWQDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-formyl-6-methoxyphenoxy)acrylate 在 盐酸 、 dirhodium tetraacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 乙酰氯 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (2S,4S,5S,6S,10R)-1'-benzyl-13-methoxy-5-(4-methylphenyl)spiro[3,11-dioxa-7-azatetracyclo[10.4.0.02,6.06,10]hexadeca-1(12),13,15-triene-4,3'-indole]-2',8-dione
  参考文献：
  名称：

  Discovery of core-structurally novel PTP1B inhibitors with specific selectivity containing oxindole-fused spirotetrahydrofurochroman by one-pot reaction

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) has been proposed to be an ideal target for treatment of type II diabetes and obesity. However, no druggable PTP1B inhibitor has been established and there is still an urgent demand for the development of structurally novel PTPIB inhibitor. Herein, we reported core-structurally novel PTP1B inhibitors with low micromole-ranged inhibitory activity by one-pot reaction from simple starting materials. Further studies demonstrated some of these active compounds had a specific selectivity over other PTPs. The structure and activity relationship was also described. The best active and selective compound 5e inhibited PTP1B activity with an IC50 of 4.53 mu M. Molecular docking analysis further demonstrated that compound 5e bound to the active pocket of PTP1B. The results might provide some insights for further development of new drugs for type II diabetes and obesity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.11.055

文献信息

• Efficient synthesis of chiral cyclic acetals by metal and Brønsted acid co-catalyzed enantioselective four-component cascade reactions
  作者：Lin Qiu、Xin Guo、Chaoqun Ma、Huang Qiu、Shunying Liu、Liping Yang、Wenhao Hu

  DOI：10.1039/c3cc49063g

  日期：——

  Four-component Mannich reactions subsequently followed by an intramolecular oxo-Michael addition were developed to efficiently produce chiral cyclic acetals with high diastereoselectivity and enantioselectivity.

  随后通过分子内氧化Michael加成反应发展了四组分Mannich反应，以高对映选择性和对映选择性高效产生手性环状缩醛。
• Diastereoselective Three-Component Cascade Reaction to Construct Oxindole-Fused Spirotetrahydro­furochroman Scaffolds for Drug Discovery
  作者：Lin Qiu、Dongwei Wang、Yubing Lei、Lixin Gao、Shunying Liu、Jia Li、Wenhao Hu

  DOI：10.1002/ejoc.201600315

  日期：2016.5

  A one-pot synthesis of new oxindole-fused polycyclic scaffolds is reported. The process involves a three-component [3+2] cycloaddition followed by cyclization through an intramolecular Michael addition. The reaction gives easy access to oxindole-fused spirotetrahydrofurochromans in moderate to good yields with high regio- and diastereoselectivity. These compounds could be useful for for drug discovery

  报道了一种新的羟吲哚融合的多环支架的一锅法合成。该过程涉及三组分 [3+2] 环加成，然后通过分子内迈克尔加成进行环化。该反应可以很容易地以中等至良好的产率获得羟吲哚稠合的螺四氢呋喃苯并具有高区域选择性和非对映选择性。这些化合物可用于药物发现。通过还原硝基和分子内酰胺形成来实现进一步的修饰，得到相应的内酰胺。所得杂环产物在体外对酶 PTP1B 显示出良好的抑制活性。
• A Novel [3+2] Dipolar Cycloaddition Approach to Hexahydrobenzofuro[3,2-<i>b</i>]pyrroles
  作者：Ikyon Kim、Hee-Kyung Na、Kyung Kim、Sun Kim、Ge Lee

  DOI：10.1055/s-2008-1077951

  日期：——

  A highly stereoselective intramolecular 1,3-dipolar cycloaddition reaction of azomethine ylides derived from 2-vinyloxybenzaldehydes proceeded smoothly to allow for a direct access to tricyclic hexahydrobenzofuro[3,2-b]pyrroles in good yields.

  由2-乙烯基氧基苯甲醛衍生的偶氮甲碱叶立德的高度立体选择性的分子内1,3-偶极环加成反应顺利进行，能够以良好的产率直接生成三环六氢苯并呋喃并[3,2-b]吡咯。