(3a'R,4'R,7'R,8a'R)-tetrahydrospiro[cyclohexane-1,2'-[1,3,5]trioxa[4,7]methano[1,3]dioxolo[4,5-c]oxepin]-6'(4'H)-one | 185900-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3a'R,4'R,7'R,8a'R)-tetrahydrospiro[cyclohexane-1,2'-[1,3,5]trioxa[4,7]methano[1,3]dioxolo[4,5-c]oxepin]-6'(4'H)-one
• 英文别名: (1R,2R,6R,8R)-spiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclohexane]-9-one
• CAS: 185900-33-8
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: SPIMCRRQMMBDIS-ZDCRXTMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3a'R,4'R,7'R,8a'R)-tetrahydrospiro[cyclohexane-1,2'-[1,3,5]trioxa[4,7]methano[1,3]dioxolo[4,5-c]oxepin]-6'(4'H)-one 在 sodium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase

  摘要：

  The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (G1-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose B-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. G1-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.

  DOI：

  10.1021/jm9607360
• 作为产物：
  描述：

  (-)-4,5-cyclohexylidenequinic acid lactone 在 4-二甲氨基吡啶 、 tris[2-phenylpyridinato-C²,N]iridium(III) 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成 (3a'R,4'R,7'R,8a'R)-tetrahydrospiro[cyclohexane-1,2'-[1,3,5]trioxa[4,7]methano[1,3]dioxolo[4,5-c]oxepin]-6'(4'H)-one
  参考文献：
  名称：

  硫代氨基甲酸酯的可见光光催化还原：无锡Barton-McCombie脱氧反应的发展

  摘要：

  Barton–McCombie脱氧是有机化学家工具箱中最重要的转变之一，这已成为许多方法学发展的主题。在这项研究中，我们报告了在可见光激活下从硫代氨基甲酸酯前体对仲醇和叔醇进行光催化的氧化还原脱氧。在Hünig碱作为牺牲电子供体的情况下，铱络合物Ir（ppy）3被证明是最有效的催化剂。提出了基于荧光猝灭实验和循环伏安法的机理研究。

  DOI：

  10.1002/adsc.201400729

文献信息

• 9-ETHYL-3,6-DIMETHYLCARBAZOLE (DMECZ)
  作者：Buck, Jason R.、Park, Minnie、Wang, Zhiwei、Prudhomme, Daniel R.、Rizzo, Carmelo J.、Chambournier, Gilles、Hart, David J.

  DOI：10.15227/orgsyn.077.0153

  日期：——
• An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and <i>m</i>-(Trifluoromethyl)benzoates
  作者：Daniel R. Prudhomme、Zhiwei Wang、Carmelo J. Rizzo

  DOI：10.1021/jo971332y

  日期：1997.11.1
• Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase
  作者：Horst Hemmerle、Hans-Joerg Burger、Peter Below、Gerrit Schubert、Robert Rippel、Peter W. Schindler、Erich Paulus、Andreas W. Herling

  DOI：10.1021/jm9607360

  日期：1997.1.1

  The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (G1-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose B-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. G1-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.
• Visible Light Photocatalytic Reduction of<i>O</i>-Thiocarbamates: Development of a Tin-Free Barton-McCombie Deoxygenation Reaction
  作者：Ludwig Chenneberg、Alexandre Baralle、Marion Daniel、Louis Fensterbank、Jean-Philippe Goddard、Cyril Ollivier

  DOI：10.1002/adsc.201400729

  日期：2014.9.15

  The Barton–McCombie deoxygenation is one of the most important transformations in the toolbox of organic chemists which has been the subject of a number of methodological developments. In this study, we report a photocatalyzed redox deoxygenation of secondary and tertiary alcohols from thiocarbamate precursors under visible light activation. The iridium complex Ir(ppy)3 proved to be the most efficient

  Barton–McCombie脱氧是有机化学家工具箱中最重要的转变之一，这已成为许多方法学发展的主题。在这项研究中，我们报告了在可见光激活下从硫代氨基甲酸酯前体对仲醇和叔醇进行光催化的氧化还原脱氧。在Hünig碱作为牺牲电子供体的情况下，铱络合物Ir（ppy）3被证明是最有效的催化剂。提出了基于荧光猝灭实验和循环伏安法的机理研究。