ethyl 8-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-3,4-dichloro-1,6-dicyano-2,5-dioxobicyclo[4.2.0]octa-3,7-diene-7-carboxylate | 1220987-19-8

• 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 8-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-3,4-dichloro-1,6-dicyano-2,5-dioxobicyclo[4.2.0]octa-3,7-diene-7-carboxylate
• 英文别名: ethyl 3,4-dichloro-1,6-dicyano-2,5-dioxo-8-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)bicyclo[4.2.0]octa-3,7-diene-7-carboxylate；Ethyl 8-(1-benzyl-4,5,6,7-tetrahydroindol-2-yl)-3,4-dichloro-1,6-dicyano-2,5-dioxobicyclo[4.2.0]octa-3,7-diene-7-carboxylate；ethyl 8-(1-benzyl-4,5,6,7-tetrahydroindol-2-yl)-3,4-dichloro-1,6-dicyano-2,5-dioxobicyclo[4.2.0]octa-3,7-diene-7-carboxylate
• CAS: 1220987-19-8
• 化学式: C₂₈H₂₁Cl₂N₃O₄
• 分子量: 534.398
• InChiKey: CECNGEURGCOAIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 8-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-3,4-dichloro-1,6-dicyano-2,5-dioxobicyclo[4.2.0]octa-3,7-diene-7-carboxylate 在 silica gel 作用下， 反应 0.03h， 生成 diethyl 7-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-3-chloro-1,5-dicyano-4-oxobicyclo[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
• 作为产物：
  描述：

  ethyl 3-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-2-propynoate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 苯 为溶剂， 反应 0.08h， 以81%的产率得到ethyl 8-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-3,4-dichloro-1,6-dicyano-2,5-dioxobicyclo[4.2.0]octa-3,7-diene-7-carboxylate
  参考文献：
  名称：

  Facile [2+2] Cycloaddition of DDQ to an Alkyne: Synthesis of Pyrrolyl- and Indolylbicyclo[4.2.0]octadienes from C-Ethynylpyrroles or C-Ethynylindoles

  摘要：

  C-乙炔基吡咯或吲哚，可通过吡咯或吲哚与卤代炔烃在活性表面上进行交叉耦合制备，与2,3-二氯-5,6-二氰基-1,4-苯醌发生[2+2]环加成反应，以几乎定量的产率生成2-吡咯基或3-吲哚基双环辛二烯。这些加成物是固态下顺磁性的电荷转移复合物，因此代表了一类新型的密集功能化吡咯和吲哚衍生物，可能作为潜在的药物候选者、高效构建模块或高级材料的前体。该反应促进了吡咯、吲哚、炔烃和醌的实用及基础化学研究。

  DOI：

  10.1055/s-0029-1217133