ethyl 3,4-dicyano-3-(3,4-dichloro-2-methoxy-5-oxo-2,5-dihydrofuran-2-yl)-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)cyclobut-1-ene-carboxylate | 1314132-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 3,4-dicyano-3-(3,4-dichloro-2-methoxy-5-oxo-2,5-dihydrofuran-2-yl)-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)cyclobut-1-ene-carboxylate
• 英文别名: ethyl 3,4-dicyano-3-(3,4-dichloro-2-methoxy-5-oxofuran-2-yl)-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)cyclobutene-1-carboxylate
• CAS: 1314132-57-4
• 化学式: C₂₂H₁₉Cl₂N₃O₅
• 分子量: 476.316
• InChiKey: VTYOAVHWPBEYJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,5,6,7-四氢吲哚 在 potassium carbonate 作用下， 反应 57.0h， 生成 ethyl 3,4-dicyano-4-(3,4-dichloro-2-methoxy-5-oxo-2,5-dihydrofuran-2-yl)-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)cyclobut-1-ene-carboxylate 、 ethyl 3,4-dicyano-3-(3,4-dichloro-2-methoxy-5-oxo-2,5-dihydrofuran-2-yl)-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)cyclobut-1-ene-carboxylate 、 6-ethyl 2-methyl 3-chloro-1,5-dicyano-4-oxo-7-(4,5,6,7-tetrahydro-1H-indol-2-yl)bicyclo[3.2.0]hepta-2,6-diene-2,6-dicarboxylate
  参考文献：
  名称：

  From 4,5,6,7-tetrahydroindole to functionalized furan-2-one–4,5,6,7-tetrahydroindole–cyclobutene sequence in two steps

  摘要：

  Ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)propynoate, readily available from 4,5,6,7-tetrahydroindole and ethyl bromopropynoate, when treated with dichlorodicyanobenzoquinone (DDQ) in methanol affords furan-2-one-4,5,6,7-tetrahydroindole-cyclobutene sequence in a 52% yield. As kinetic and minor products, a furan-2-one isomer along with bicycloheptadienone have been either isolated or identified. The reaction has been shown to proceed via the isolable intermediate the [2+2]-cycloadduct of ethyl 3-(4,5,6,7-tetrahydroindo1-2-yl)propynoate with DDQ. Other alcohols react with the [2+2]-cycloadduct in a similar way. The effect of the alcohol structure on the products ratio has been analyzed. All the intermediates and products are formed as single diastereomer, thus indicating a concerted character of the rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.018

文献信息

• From 4,5,6,7-tetrahydroindole to functionalized furan-2-one–4,5,6,7-tetrahydroindole–cyclobutene sequence in two steps
  作者：Lyubov N. Sobenina、Zinaida V. Stepanova、Igor’ A. Ushakov、Al’bina I. Mikhaleva、Denis N. Tomilin、Ol’ga N. Kazheva、Grigorii G. Alexandrov、Oleg A. Dyachenko、Boris A. Trofimov

  DOI：10.1016/j.tet.2011.05.018

  日期：2011.7

  Ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)propynoate, readily available from 4,5,6,7-tetrahydroindole and ethyl bromopropynoate, when treated with dichlorodicyanobenzoquinone (DDQ) in methanol affords furan-2-one-4,5,6,7-tetrahydroindole-cyclobutene sequence in a 52% yield. As kinetic and minor products, a furan-2-one isomer along with bicycloheptadienone have been either isolated or identified. The reaction has been shown to proceed via the isolable intermediate the [2+2]-cycloadduct of ethyl 3-(4,5,6,7-tetrahydroindo1-2-yl)propynoate with DDQ. Other alcohols react with the [2+2]-cycloadduct in a similar way. The effect of the alcohol structure on the products ratio has been analyzed. All the intermediates and products are formed as single diastereomer, thus indicating a concerted character of the rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.