(E)-5-methoxy-2-(2-nitrovinyl)-1H-indole

• 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: (E)-5-methoxy-2-(2-nitrovinyl)-1H-indole
• 英文别名: 5-methoxy-2-[(E)-2-nitroethenyl]-1H-indole
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: TYDVQLKKHXDCAB-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-methoxy-2-(2-nitrovinyl)-1H-indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 5-methoxytryptamine
  参考文献：
  名称：

  2-[N-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists

  摘要：

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.

  DOI：

  10.1021/jm970721h
• 作为产物：
  描述：

  5-甲氧基吲哚-2-羧酸甲酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.25h， 生成 (E)-5-methoxy-2-(2-nitrovinyl)-1H-indole
  参考文献：
  名称：

  2-[N-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists

  摘要：

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.

  DOI：

  10.1021/jm970721h

文献信息

• Sulfinate and Carbene Co‐catalyzed Rauhut–Currier Reaction for Enantioselective Access to Azepino[1,2‐ <i>a</i> ]indoles
  作者：Xingxing Wu、Liejin Zhou、Rakesh Maiti、Chengli Mou、Lutai Pan、Yonggui Robin Chi

  DOI：10.1002/anie.201810879

  日期：2019.1.8

  A carbene and sulfinate co‐catalyzed intermolecular Rauhut–Currier reaction between enals and nitrovinyl indoles is disclosed. The carbene catalyst activates the enal and the sulfinate co‐catalyst activates the nitrovinyl indole. Both activation processes are realized via the formation of covalent bonds between the catalysts and substrates to generate catalyst‐bound intermediates. The dual catalytic

  揭示了烯与亚硝基吲哚之间的卡宾和亚磺酸盐共催化的分子间Rauhut-Currier反应。卡宾催化剂活化烯醛，亚磺酸盐助催化剂活化硝基乙烯基吲哚。两种活化过程都是通过在催化剂和底物之间形成共价键以生成与催化剂结合的中间体来实现的。双重催化反应可提供具有出色立体选择性的氮杂环庚烷[1,2- a ]吲哚产物。我们的研究表明，亚磺酸盐作为一种有效的亲核催化剂，可以在活化电子不足的烯烃以进行不对称反应中发挥独特作用。这种双重催化方法也应鼓励对亚磺酸盐和卡宾催化剂的未来开发进行新的反应。
• Asymmetric Synthesis of Pyrroloindolones by N-Heterocyclic Carbene Catalyzed [2+3] Annulation of α-Chloroaldehydes with Nitrovinylindoles
  作者：Qijian Ni、Huan Zhang、André Grossmann、Charles C. J. Loh、Carina Merkens、Dieter Enders

  DOI：10.1002/anie.201305957

  日期：2013.12.16

  NHC‐enolate plus 3: N‐heterocyclic carbenes (NHCs) serve as organocatalysts for the [2+3] annulation of nitrovinylindoles with α‐chloroaldehydes via an intermediate azolium enolate. The method provides trans‐disubstituted pyrroloindolones with good yields and excellent diastereo‐ and enantioselectivities. Further transformations lead to tetracyclic pyrrolo[1,2‐a]indoles with potential psychotropic

  NHC-烯酸酯加3：N-杂环卡宾（NHCs）用作有机催化剂，通过中间的偶氮烯醇烯酸酯与α-氯醛进行[2 + 3]的硝基乙烯基吲哚环化。该方法提供了具有良好收率和出色的非对映和对映选择性的反式-双取代吡咯并吲哚酮。进一步的转化导致具有潜在精神活性和其他生物活性的四环吡咯并[1,2- a ]吲哚。
• One-Pot Organocatalytic Asymmetric Synthesis of 1H-Pyrrolo[1,2a]indol-3(2H)-ones via a Michael-Hemiaminalization-Oxidation Sequence
  作者：Dieter Enders、Chuan Wang、Xuena Yang、Gerhard Raabe

  DOI：10.1055/s-0030-1259326

  日期：2011.3

  An efficient one-pot organocatalytic asymmetric synthesis of 1,2-cis-disubstituted 1H-pyrrolo[1,2a]indol-3(2H)-ones in moderate to good overall yields (49-68%) is presented. The ­Michael-hemiaminalization-oxidation sequence occurs with very high asymmetric induction and, after purification, virtually stereo­isomerically pure products were obtained (>98% de, >99% ee).

  本文介绍了一种高效的一锅法有机催化不对称合成1,2-顺式二取代1H-吡咯并[1,2a]吲哚-3(2H)-酮的方法，总收率中等至良好（49-68%）。迈克尔-半氨基化-氧化反应序列具有很高的不对称诱导率，纯化后几乎获得了立体纯度很高的产物（de>98%，ee>99%）。
• 2-[<i>N</i>-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists
  作者：Gilberto Spadoni、Cesarino Balsamini、Annalida Bedini、Giuseppe Diamantini、Barbara Di Giacomo、Andrea Tontini、Giorgio Tarzia、Marco Mor、Pier Vincenzo Plazzi、Silvia Rivara、Romolo Nonno、Marilou Pannacci、Valeria Lucini、Franco Fraschini、Bojidar Michaylov Stankov

  DOI：10.1021/jm970721h

  日期：1998.9.1

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.