4-[3-(trifluoromethyl)phenyl]-3-butyn-2-one | 265661-05-0

• 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: 4-[3-(trifluoromethyl)phenyl]-3-butyn-2-one
• 英文别名: 3-Butyn-2-one, 4-[3-(trifluoromethyl)phenyl]-；4-[3-(trifluoromethyl)phenyl]but-3-yn-2-one
• CAS: 265661-05-0
• 化学式: C₁₁H₇F₃O
• 分子量: 212.171
• InChiKey: PPALXWYMAHPYHO-UHFFFAOYSA-N

物化性质

• 沸点：
  264.5±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[3-(trifluoromethyl)phenyl]-3-butyn-2-one 在 potassium hydrogencarbonate 、 hydroxylamine-O-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2E)-3-(dimethylamino)-1-{6-methyl-2-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-b]pyridazin-3-yl}-2-propen-1-one
  参考文献：
  名称：

  N-Phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amines as Potent and Selective Inhibitors of Glycogen Synthase Kinase 3 with Good Cellular Efficacy

  摘要：

  Glycogen synthase kinase 3 regulates glycogen synthase, the rate-determining enzyme for glycogen synthesis. Liver and muscle glycogen synthesis is defective in type 2 diabetics, resulting in elevated plasma glucose levels. Inhibition of GSK-3 could potentially be an effective method to control plasma glucose levels in type 2 diabetics. Structure-activity studies on a N-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine series have led to the identification of potent and selective compounds with good cellular efficacy. Molecular modeling studies have given insights into the mode of binding of these inhibitors. Since the initial leads were also potent inhibitors of CDK-2/CDK-4, an extensive SAR was performed at various positions of the pyrazolo[1,5-b]pyridazin core to afford potent GSK-3 inhibitors that were highly selective over CDK-2. In addition, these inhibitors also exhibited very good cell efficacy and functional response. A representative example was shown to have good oral exposure levels, extending their utility in an in vivo setting. These inhibitors provide a viable lead series in the discovery of new therapies for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm040063i
• 作为产物：
  描述：

  4-[3-(trifluoromethyl)phenyl]but-3-yn-2-ol 在 peroxygenase from Agrocybe aegerita 、 双氧水 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 5.0h， 以93%的产率得到4-[3-(trifluoromethyl)phenyl]-3-butyn-2-one
  参考文献：
  名称：

  用于合成对映体纯炔丙醇和胺的生物催化平台

  摘要：

  炔丙醇和胺是有机合成中的通用组成部分。我们展示了一种简单的酶级联反应，可以从容易获得的外消旋起始材料合成对映异构纯的炔丙醇和胺。在第一步中，来自Agrocybe aegerita的过氧化酶将外消旋炔丙醇转化为相应的酮，然后使用来自开菲尔乳杆菌的 ( R )-选择性醇脱氢酶或 ( S )-选择性醇脱氢酶将其转化为对映体纯醇来自布罗基热厌氧菌. 此外，使用来自土曲霉的( R )-选择性胺转氨酶或来自紫色色杆菌的( S )-选择性胺转氨酶，建立了将外消旋醇酶促Mitsunobu型转化为对映体富集的炔丙基胺。一锅两步级联反应以 70-99% 的产率产生了范围广泛的对映体富集的醇和胺产物。

  DOI：

  10.1021/acs.orglett.2c01547

文献信息

• Synthesis of di- and poly-substituted phenols via [4 + 2] type cyclo-condensation
  作者：Ming-Zhe Shao、Xiao-Yu Liu、Fang-Qing Li、Zili Chen

  DOI：10.1016/j.tetlet.2021.153031

  日期：2021.5

  A new [4 + 2] type cyclocondensation was developed to prepare 3,5- and poly-substituted phenols using aryl ketoesters and ynones as the starting materials; Various substrates, such as aryl-, heteroaryl ketoesters and aryl-, vinyl-, alkyl substituted ynones, were employed. In addition, extending the substrate scope to benzoyl acetone provided 3,4,5-trisubstituted phenols.

  开发了一种新的[4 + 2]型环缩合反应，以芳基酮酸酯和ynones为起始原料制备3,5-和多取代的苯酚。使用了各种底物，例如芳基-，杂芳基酮酸酯和芳基-，乙烯基-，烷基取代的炔酮。另外，将底物范围扩展至苯甲酰基丙酮，提供了3,4,5-三取代的苯酚。
• [EN] PYRADAZINE COMPOUNDS AS GSK-3 INHIBITORS<br/>[FR] COMPOSES DE PYRADAZINE UTILES COMME INHIBITEURS DE GSK-3
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004035588A1

  公开（公告）日：2004-04-29

  The present invention relates generally to inhibitors of the kinases, such as GSK3, and more particularly to fused pyradazine compounds according to formula (I) and methods of their use.

  本发明通常涉及激酶抑制剂，如GSK3，更具体地涉及根据式(I)的融合吡啶并嘧啶化合物及其使用方法。
• Pyradazine compounds as gsk-3 inhibitors
  申请人：Dickerson Howard Scott

  公开号：US20060069097A1

  公开（公告）日：2006-03-30

  The present invention relates generally to inhibitors of the kinases, such as GSK3, and more particularly to fused pyradazine compounds and methods of their use.

  本发明通常涉及抑制激酶的抑制剂，例如GSK3，更具体地涉及融合嘧啶二氮杂环化合物及其使用方法。
• METHODS OF SYNTHESIZING CINACALCET AND SALTS THEREOF
  申请人：Thiel Oliver

  公开号：US20090137837A1

  公开（公告）日：2009-05-28

  Methods of preparing cinacalcet, cinacalcet derivatives, and salts thereof is disclosed herein. Also disclosed herein are polymorphs of cinacalcet, compositions of cinacalcet, and methods of treating a subject by administering cinacalcet, wherein cinacalcet is prepared by the disclosed methods.

  本文披露了制备西那卡塞、西那卡塞衍生物和其盐的方法。本文还披露了西那卡塞的多晶形态、组合物以及通过给予西那卡塞治疗受试者的方法，其中西那卡塞是通过披露的方法制备的。
• PYRADAZINE COMPOUNDS AS GSK-3 INHIBITORS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1551842A1

  公开（公告）日：2005-07-13