2-(4'-methoxy-4-oxo-1,4-dihydro-[1,1'-biphenyl]-1-yl)ethyl 2-nitrobenzenesulfonate | 1394170-80-9

• 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: 2-(4'-methoxy-4-oxo-1,4-dihydro-[1,1'-biphenyl]-1-yl)ethyl 2-nitrobenzenesulfonate
• 英文别名: 2-[1-(4-Methoxyphenyl)-4-oxocyclohexa-2,5-dien-1-yl]ethyl 2-nitrobenzenesulfonate；2-[1-(4-methoxyphenyl)-4-oxocyclohexa-2,5-dien-1-yl]ethyl 2-nitrobenzenesulfonate
• CAS: 1394170-80-9
• 化学式: C₂₁H₁₉NO₇S
• 分子量: 429.45
• InChiKey: NAMNQVLZAZWING-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4'-methoxy-4-oxo-1,4-dihydro-[1,1'-biphenyl]-1-yl)ethyl 2-nitrobenzenesulfonate 在 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 sceletenone
  参考文献：
  名称：

  Oxidative ipso-Rearrangement Performed by a Hypervalent Iodine Reagent and Its Application

  摘要：

  An oxidative ipso-rearrangement mediated by a hypervalent iodine reagent that enables rapid generation of a functionalized dienone system containing a quaternary carbon center connected to several sp(2) centers has been developed. The process occurs through transfer of an aryl group from a silyl segment present on the lateral chain. As an illustration of the potential of this transformation, a total synthesis of sceletenone, a small alkaloid, is described.

  DOI：

  10.1021/jo301408j
• 作为产物：
  描述：

  1-(2-hydroxyethyl)-4'-methoxy-1,4-dihydro-[1,1'-biphenyl]-4-ol 在 4-二甲氨基吡啶 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(4'-methoxy-4-oxo-1,4-dihydro-[1,1'-biphenyl]-1-yl)ethyl 2-nitrobenzenesulfonate
  参考文献：
  名称：

  Oxidative ipso-Rearrangement Performed by a Hypervalent Iodine Reagent and Its Application

  摘要：

  An oxidative ipso-rearrangement mediated by a hypervalent iodine reagent that enables rapid generation of a functionalized dienone system containing a quaternary carbon center connected to several sp(2) centers has been developed. The process occurs through transfer of an aryl group from a silyl segment present on the lateral chain. As an illustration of the potential of this transformation, a total synthesis of sceletenone, a small alkaloid, is described.

  DOI：

  10.1021/jo301408j

文献信息

• Oxidative <i>ipso</i>-Rearrangement Performed by a Hypervalent Iodine Reagent and Its Application
  作者：Guillaume Jacquemot、Sylvain Canesi

  DOI：10.1021/jo301408j

  日期：2012.9.7

  An oxidative ipso-rearrangement mediated by a hypervalent iodine reagent that enables rapid generation of a functionalized dienone system containing a quaternary carbon center connected to several sp(2) centers has been developed. The process occurs through transfer of an aryl group from a silyl segment present on the lateral chain. As an illustration of the potential of this transformation, a total synthesis of sceletenone, a small alkaloid, is described.