3,5-difluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-difluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde
• 英文别名: 3,5-Difluoro-2-(3-methylbut-2-enoxy)benzaldehyde；3,5-difluoro-2-(3-methylbut-2-enoxy)benzaldehyde
• 化学式: C₁₂H₁₂F₂O₂
• 分子量: 226.223
• InChiKey: MBZLGYFNXYAFPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-difluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde 、 N-Boc-氨基丙炔 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 1.5h， 以54%的产率得到1-{3,5-difluoro-2-[(3-methylbut-2-en-1-yl)oxy] phenyl}-3-N-Boc-methylaminoprop-2-yn-ol
  参考文献：
  名称：

  A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines

  摘要：

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.087
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 、 3,5-二氟水杨醛 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以79%的产率得到3,5-difluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde
  参考文献：
  名称：

  A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines

  摘要：

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.087

文献信息

• ABCA1 elevating compounds
  申请人：Abelman Matthew

  公开号：US20070010544A1

  公开（公告）日：2007-01-11

  The present invention provides compounds useful for increasing cellular ATP binding cassette transporter ABCA1 production in mammals, and to methods of using such compounds in the treatment of coronary artery diseases, dyslipidiemias and metabolic syndrome. The invention also relates to methods for the preparation of such compounds, and to pharmaceutical compositions containing them.

  本发明提供了一种用于增加哺乳动物细胞ATP结合盒转运蛋白ABCA1产生的化合物，以及使用这种化合物治疗冠状动脉疾病、血脂异常和代谢综合征的方法。该发明还涉及制备这种化合物的方法，以及含有它们的药物组合物。
• Enantioselective Alkynylation Reactions to Substituted Benzaldehyde and Salicylaldehyde Derivatives: The Effect of Substituents upon the Efficiency and Enantioselectivity
  作者：Elizabeth Tyrrell、Kibur Hunie Tesfa、Alastair Mann、Kuldip Singh

  DOI：10.1055/s-2007-966045

  日期：——

  Asymmetric alkynylation reactions to mono-, di-, and trisubstituted aromatic aldehydes have been accomplished in good yields and with a range of selectivities. For salicylaldehyde derivatives both the yield and the enantioselectivity of the alkynylation reaction appears to depend not only upon the electron-donating/ electron-withdrawing nature of substituents but also upon their position in the ring

  单、二和三取代芳香醛的不对称炔基化反应已经以良好的收率和一系列选择性完成。对于水杨醛衍生物，炔基化反应的产率和对映选择性似乎不仅取决于取代基的给电子/吸电子性质，还取决于它们在环中相对于羰基的位置。对于苯甲醛衍生物，这种观察以硝基苯甲醛为例，其中用 3-硝基苯甲醛进行的不对称炔基化以几乎定量的产率和对映选择性发生。相比之下，我们用 4-硝基苯甲醛进行不对称炔基化的尝试失败了。
• ABCA1 ELEVATING COMPOUNDS
  申请人：Abelman Matthew

  公开号：US20080293757A1

  公开（公告）日：2008-11-27

  The present invention provides compounds useful for increasing cellular ATP binding cassette transporter ABCA1 production in mammals, and to methods of using such compounds in the treatment of coronary artery diseases, dyslipidiemias and metabolic syndrome. The invention also relates to methods for the preparation of such compounds, and to pharmaceutical compositions containing them.

  本发明提供了一种用于增加哺乳动物细胞ATP结合盒转运蛋白ABCA1生产的化合物，并提供了使用这种化合物治疗冠状动脉疾病、血脂异常和代谢综合征的方法。本发明还涉及制备这种化合物的方法，以及含有它们的制药组合物。
• The synthesis and biological evaluation of a range of novel functionalised benzopyrans as potential potassium channel activators
  作者：Elizabeth Tyrrell、Kibur Hunie Tesfa、Iain Greenwood、Alistair Mann

  DOI：10.1016/j.bmcl.2007.11.135

  日期：2008.2

  A range of novel benzopyrans have been synthesised and biologically evaluated for K-ATP channel activity employing cromakalim 1 as a benchmark K-ATP channel opener. Although the compounds that were evaluated demonstrated a reduced ability to relax phenylephrine stimulated rat thoracic tissue, we provide evidence that benzopyrans 7a-h may be operating via an alternative mechanism than ATP-sensitive K+ channel activity. (C) 2008 Published by Elsevier Ltd.
• US7423045B2
  申请人：——

  公开号：US7423045B2

  公开（公告）日：2008-09-09