ethyl 2-hydroxy-7,7-dimethyl-5-oxo-4-phenyl-3,4,5,6,7,8-hexahydro-2H-chromene-2-carboxylate | 1233334-63-8

• 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: ethyl 2-hydroxy-7,7-dimethyl-5-oxo-4-phenyl-3,4,5,6,7,8-hexahydro-2H-chromene-2-carboxylate
• 英文别名: Ethyl 2-hydroxy-7,7-dimethyl-5-oxo-4-phenyl-3,4,6,8-tetrahydrochromene-2-carboxylate
• CAS: 1233334-63-8
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: MYWNHTJAAOYSEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-7,7-dimethyl-5-oxo-4-phenyl-3,4,5,6,7,8-hexahydro-2H-chromene-2-carboxylate 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到ethyl 7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents

  摘要：

  A series of 2,4-disubstituted polyhydroquinoline were synthesized and evaluated for their in vivo antihyperglycemic as well as antidyslipidemic activities. Several synthesized compounds have exhibited promising in vivo antihyperglycemic in SLM, STZ-S, and db/db mice model along with significant lipid and TG modulating activity. All these compounds were evaluated in various in vitro models of diabetes to know the possible mechanism of their antihyperglycemic action. Interestingly, compounds 3a-r (diaryl substitution) have exhibited promising protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity whereas, compounds 5a-d (acid substituted) have shown significant glycogen phosphorylase activity. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.11.061
• 作为产物：
  描述：

  (E)-ethyl-2-oxo-4-phenylbut-3-enoate 、 5,5-二甲基-1,3-环己二酮 在 copper acetylacetonate 、 1,1′-di((8S,9S)-6′-methoxycinchonan-9-yl)-4,4′-bi-1,2,3-triazole 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 ethyl 2-hydroxy-7,7-dimethyl-5-oxo-4-phenyl-3,4,5,6,7,8-hexahydro-2H-chromene-2-carboxylate
  参考文献：
  名称：

  单击二聚金鸡纳生物碱

  摘要：

  使用bis（TMS）丁二炔和其他二价炔烃，在铜催化的1,3-偶极“点击”环加成中以高收率获得了一系列Cinchona生物碱衍生的二聚体。具有三氮唑连接基的产物是不对称铜催化的迈克尔加成反应的有效配体。结果表明，这种连接基的存在是有效手性转移的原因。

  DOI：

  10.1021/acs.joc.6b01403

文献信息

• Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents
  作者：Atul Kumar、Siddharth Sharma、Vishwa Deepak Tripathi、Ram Awatar Maurya、Swayam Prakash Srivastava、Gitika Bhatia、A.K. Tamrakar、Arvind Kumar Srivastava

  DOI：10.1016/j.bmc.2009.11.061

  日期：2010.6.1

  A series of 2,4-disubstituted polyhydroquinoline were synthesized and evaluated for their in vivo antihyperglycemic as well as antidyslipidemic activities. Several synthesized compounds have exhibited promising in vivo antihyperglycemic in SLM, STZ-S, and db/db mice model along with significant lipid and TG modulating activity. All these compounds were evaluated in various in vitro models of diabetes to know the possible mechanism of their antihyperglycemic action. Interestingly, compounds 3a-r (diaryl substitution) have exhibited promising protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity whereas, compounds 5a-d (acid substituted) have shown significant glycogen phosphorylase activity. (C) 2009 Published by Elsevier Ltd.
• <i>Click</i>-Dimerized <i>Cinchona</i> Alkaloids
  作者：Przemysław J. Boratyński、Rafał Kowalczyk

  DOI：10.1021/acs.joc.6b01403

  日期：2016.9.2

  A series of Cinchona alkaloid-derived dimers were obtained in high yields in copper-catalyzed 1,3-dipolar “click” cycloaddition using bis(TMS)butadiyne and other bivalent alkynes. The products with bitriazole linkers were effective ligands for asymmetric copper-catalyzed Michael addition. It was shown that the presence of such linker was responsible for effective chirality transfer.

  使用bis（TMS）丁二炔和其他二价炔烃，在铜催化的1,3-偶极“点击”环加成中以高收率获得了一系列Cinchona生物碱衍生的二聚体。具有三氮唑连接基的产物是不对称铜催化的迈克尔加成反应的有效配体。结果表明，这种连接基的存在是有效手性转移的原因。