tert-butyl N-[5-(2-formyl-3,5-dihydroxy-4-methylphenyl)pent-4-ynyl]carbamate | 859507-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[5-(2-formyl-3,5-dihydroxy-4-methylphenyl)pent-4-ynyl]carbamate
• CAS: 859507-90-7
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: CQIHHBPFXWJTSW-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  546.2±39.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[5-(2-formyl-3,5-dihydroxy-4-methylphenyl)pent-4-ynyl]carbamate 在 Au(OAc)3 、 四丁基氟化铵 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 [7-Methyl-3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-6,8-dioxoisochromen-7-yl] quinoxaline-2-carboxylate
  参考文献：
  名称：

  Synthesis of Azaphilone-Based Chemical Libraries

  摘要：

  The synthesis of azaphilone scaffolds that have been further diversified by cross coupling acylation and amine addition is reported. Methodology development also led to novel modifications including CS acetoxylation and condensations producing isoquinolin-6(7H) structures. Overall, the library synthesis afforded three azaphilone sublibraries, including vinylogous pyridones which project diversity elements in four sectors of the azaphilone core.

  DOI：

  10.1021/co300002x
• 作为产物：
  描述：

  N-(4-戊炔基)氨基甲酸叔丁酯 、 6-bromo-2,4-dihydroxy-3-methylbenzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以88%的产率得到tert-butyl N-[5-(2-formyl-3,5-dihydroxy-4-methylphenyl)pent-4-ynyl]carbamate
  参考文献：
  名称：

  Synthesis of Azaphilone-Based Chemical Libraries

  摘要：

  The synthesis of azaphilone scaffolds that have been further diversified by cross coupling acylation and amine addition is reported. Methodology development also led to novel modifications including CS acetoxylation and condensations producing isoquinolin-6(7H) structures. Overall, the library synthesis afforded three azaphilone sublibraries, including vinylogous pyridones which project diversity elements in four sectors of the azaphilone core.

  DOI：

  10.1021/co300002x

文献信息

• Synthesis of the Azaphilones Using Copper-Mediated Enantioselective Oxidative Dearomatization
  作者：Jianglong Zhu、Nicholas P. Grigoriadis、Jonathan P. Lee、John A. Porco

  DOI：10.1021/ja052049g

  日期：2005.7.1

  An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.