1,6-Dimethyl-4,7-dioxo-2-phenyl-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,6-Dimethyl-4,7-dioxo-2-phenyl-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1,6-dimethyl-4,7-dioxo-2-phenylindole-3-carboxylate
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: SOZLPEQZIFICGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氟甲烷磺酸甲酯 、 (Z)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(2-phenyl-oxazol-5-yl)-hept-5-en-2-ynoic acid ethyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 benzyltrimethylammonium cyanide 作用下， 生成 1,6-Dimethyl-4,7-dioxo-2-phenyl-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester 、 4,7-Dihydroxy-1,6-dimethyl-2-phenyl-1H-indole-3-carboxylic acid ethyl ester 、 4-(tert-Butyl-dimethyl-silanyloxy)-1,6-dimethyl-7-oxo-2-phenyl-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester 、 4-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-1,6-dimethyl-2-phenyl-1H-indole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Competing Pathways in the Azomethine Ylide Route to Indoloquinones:  An Improved Procedure for the Generation of a Transient 4-Oxazoline from the Oxazolium Salt

  摘要：

  Azomethine ylide generation from the oxazolium salt 22 and PhSiH3/CsF affords complex products derived from the initial cycloadduct 23 via three competing pathways. Colorless intermediates 24-27 have been detected, and their oxidation products 10, 28, and 29 have been identified. Nucleophilic activation of the oxazolium salt 22 is reported using the organic-soluble benzyltrimethylammonium cyanide. This variation affords the unstable cycloadduct 32, which undergoes aromatization via a single pathway involving 24 and 27, and DDQ oxidation gives the indoloquinone 10 in an improved 63% yield. Lower yields using PhSiH3/CsF or NaCN activation methods are attributed to the heterogeneous conditions and interception of the azomethine ylide by unreacted oxazolium salt.

  DOI：

  10.1021/jo9702195

文献信息

• Competing Pathways in the Azomethine Ylide Route to Indoloquinones:  An Improved Procedure for the Generation of a Transient 4-Oxazoline from the Oxazolium Salt
  作者：Edwin Vedejs、Sean D. Monahan

  DOI：10.1021/jo9702195

  日期：1997.7.1

  Azomethine ylide generation from the oxazolium salt 22 and PhSiH3/CsF affords complex products derived from the initial cycloadduct 23 via three competing pathways. Colorless intermediates 24-27 have been detected, and their oxidation products 10, 28, and 29 have been identified. Nucleophilic activation of the oxazolium salt 22 is reported using the organic-soluble benzyltrimethylammonium cyanide. This variation affords the unstable cycloadduct 32, which undergoes aromatization via a single pathway involving 24 and 27, and DDQ oxidation gives the indoloquinone 10 in an improved 63% yield. Lower yields using PhSiH3/CsF or NaCN activation methods are attributed to the heterogeneous conditions and interception of the azomethine ylide by unreacted oxazolium salt.