methyl 2-(2-diazo-3-oxooct-7-enoyl)benzoate | 864718-97-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 2-(2-diazo-3-oxooct-7-enoyl)benzoate
• 英文别名: Methyl 2-(2-diazo-3-oxooct-7-enoyl)benzoate
• CAS: 864718-97-8
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: NPKRTLAOEVZFNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-diazo-3-oxooct-7-enoyl)benzoate 在 dirhodium tetraacetate 作用下， 以 苯 为溶剂， 反应 0.5h， 以75%的产率得到
  参考文献：
  名称：

  Efficient Construction of the Oxatricyclo[6.3.1.0^0,0]dodecane Core of Komaroviquinone Using a Cyclization/Cycloaddition Cascade of a Rhodium Carbenoid Intermediate

  摘要：

  The rhodium(ll)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures.

  DOI：

  10.1021/ol0513589
• 作为产物：
  描述：

  2-(氯羰基)苯甲酸甲酯 在 p-nitrobenzenesulfonyl azide 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 methyl 2-(2-diazo-3-oxooct-7-enoyl)benzoate
  参考文献：
  名称：

  Efficient Construction of the Oxatricyclo[6.3.1.0^0,0]dodecane Core of Komaroviquinone Using a Cyclization/Cycloaddition Cascade of a Rhodium Carbenoid Intermediate

  摘要：

  The rhodium(ll)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures.

  DOI：

  10.1021/ol0513589

文献信息

• Efficient Construction of the Oxatricyclo[6.3.1.0^0,0]dodecane Core of Komaroviquinone Using a Cyclization/Cycloaddition Cascade of a Rhodium Carbenoid Intermediate
  作者：Albert Padwa、Jutatip Boonsombat、Paitoon Rashatasakhon、Jerremey Willis

  DOI：10.1021/ol0513589

  日期：2005.8.1

  The rhodium(ll)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures.
• A Rh(II)-catalyzed cycloaddition approach toward the synthesis of komaroviquinone
  作者：Albert Padwa、Majid J. Chughtai、Jutatip Boonsombat、Paitoon Rashatasakhon

  DOI：10.1016/j.tet.2008.01.129

  日期：2008.5

  Using a rhodium (II)-catalyzed cyclization/cycloaddition sequence as the key reaction step, the icetexane core of komaroviquinone was constructed by an intramolecular dipolar-cycloaddition of a carbonyl ylide dipole across a tethered pi-bond. The ylide was arrived at by cyclization of a rhodium carbenoid intermediate onto a proximal ester group. Efforts toward the preparation of the required precursor for elaboration to the natural product are discussed. (C) 2008 Elsevier Ltd. All rights reserved.