2,2-dimethyl-4-vinyl-2H-chromene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2-dimethyl-4-vinyl-2H-chromene
• 英文别名: 4-Ethenyl-2,2-dimethylchromene
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: AUOMRTJSWVSWBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-4-vinyl-2H-chromene 、 4-(N-马来酰亚胺基)二苯甲酮 以 甲苯 为溶剂， 反应 24.0h， 生成 (3aR,3bS,11aS)-2-(4-benzoylphenyl)-4,4-dimethyl-3a,3b,11,11a-tetrahydrochromeno[3,4-e]isoindole-1,3-dione
  参考文献：
  名称：

  Antidiabetic and Antiobesity Effects of Ampkinone (6f), a Novel Small Molecule Activator of AMP-Activated Protein Kinase

  摘要：

  Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (6f), as an indirect AMPK activator, which was derived from the small molecule library constructed by diversity-oriented synthesis. Ampkinone stimulated the phosphorylation of AMPK via the indirect activation of AMPK in various cell lines. Ampkinone-mediated activation of AMPK required the activity of LKB1 and resulted in increased glucose uptake in muscle cells. In addition, ampkinone-treated DIO mice significantly reduced total body weight and overall fat mass. Histological examination and measurement of lipid parameters showed that ampkinone effectively improved metabolic abnormalities in the DIO mice model. Our results demonstrate that ampkinone, a small molecule with a privileged benzopyran substructure, has a potential as a new class of therapeutic agent for antidiabetic and antiobesity treatment via the indirect stimulation of AMPK.

  DOI：

  10.1021/jm100565d
• 作为产物：
  描述：

  1-iodo-2-(vinyloxy)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 56.0h， 生成 2,2-dimethyl-4-vinyl-2H-chromene 、 2-isopropyl-3-vinylbenzofuran
  参考文献：
  名称：

  铑催化的萘酚或苯酚连接的1，6-烯炔的分子内环化通过sp2 C的裂解和形成？O键

  摘要：

  戴上一个戒指：阳离子铑/双键合络合物催化萘酚或苯酚连接的1,6-烯炔的分子内环化反应，通过裂解和形成sp生成乙烯基萘或乙烯基苯并呋喃以及乙烯基萘或乙烯基苯并吡喃。2个ç  O键。机理研究表明，目前的环化反应是通过从阳离子Rhodacycle中间体中消除β-氧来进行的。

  DOI：

  10.1002/anie.201201186

文献信息

• Rhodium-Catalyzed Intramolecular Cyclization of Naphthol- or Phenol-Linked 1,6-Enynes Through the Cleavage and Formation of sp²CO Bonds
  作者：Norifumi Sakiyama、Keiichi Noguchi、Ken Tanaka

  DOI：10.1002/anie.201201186

  日期：2012.6.11

  Put a ring on it: A cationic rhodium(I)/binap complex catalyzes the intramolecular cyclization reactions of naphthol‐ or phenol‐linked 1,6‐enynes to produce vinylnaphtho‐ or vinylbenzofurans and vinylnaphtho‐ or vinylbenzopyrans through the cleavage and formation of sp2 CO bonds. Mechanistic studies imply that the present cyclization reactions proceed through β‐oxygen elimination from cationic rhodacycle

  戴上一个戒指：阳离子铑/双键合络合物催化萘酚或苯酚连接的1,6-烯炔的分子内环化反应，通过裂解和形成sp生成乙烯基萘或乙烯基苯并呋喃以及乙烯基萘或乙烯基苯并吡喃。2个ç  O键。机理研究表明，目前的环化反应是通过从阳离子Rhodacycle中间体中消除β-氧来进行的。
• Antidiabetic and Antiobesity Effects of Ampkinone (<b>6f</b>), a Novel Small Molecule Activator of AMP-Activated Protein Kinase
  作者：Sangmi Oh、Sung Jin Kim、Jung Hwan Hwang、Hyang Yeon Lee、Min Jeong Ryu、Jongmin Park、Soung Jung Kim、Young Suk Jo、Yong Kyung Kim、Chul-Ho Lee、Ki Ryang Kweon、Minho Shong、Seung Bum Park

  DOI：10.1021/jm100565d

  日期：2010.10.28

  Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (6f), as an indirect AMPK activator, which was derived from the small molecule library constructed by diversity-oriented synthesis. Ampkinone stimulated the phosphorylation of AMPK via the indirect activation of AMPK in various cell lines. Ampkinone-mediated activation of AMPK required the activity of LKB1 and resulted in increased glucose uptake in muscle cells. In addition, ampkinone-treated DIO mice significantly reduced total body weight and overall fat mass. Histological examination and measurement of lipid parameters showed that ampkinone effectively improved metabolic abnormalities in the DIO mice model. Our results demonstrate that ampkinone, a small molecule with a privileged benzopyran substructure, has a potential as a new class of therapeutic agent for antidiabetic and antiobesity treatment via the indirect stimulation of AMPK.