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

文献信息

• Facile [2+2] Cycloaddition of DDQ to an Alkyne: Synthesis of Pyrrolyl- and Indolylbicyclo[4.2.0]octadienes from C-Ethynylpyrroles or C-Ethynylindoles
  作者：Boris Trofimov、Lyubov’ Sobenina、Zinaida Stepanova、Igor’ Ushakov、Lidiya Sinegovskaya、Tamara Vakul’skaya、Al’bina Mikhaleva

  DOI：10.1055/s-0029-1217133

  日期：2010.2

  C-Ethynylpyrroles or -indoles, which can be prepared by cross-coupling of pyrroles or indoles with haloalkynes on active surfaces, undergo [2+2]-cycloaddition reactions with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to give 2-pyrrolyl- or 3-indolylbicyclooctadienes in almost quantitative yields. The adducts are charge-transfer complexes that are paramagnetic in the solid state, and therefore represent a new family of densely functionalized pyrrole and indole derivatives potentially useful as pharmaceutical candidates, highly potent building blocks, or precursors of advanced materials. The reaction contributes to the practical and basic chemistry of pyrroles, indoles, alkynes, and quinones.

  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。
• 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.