Ethyl 3'-<1-(phenylsulfonyl)-3-(bromomethyl)indol-2-yl>acrylate | 958238-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 3'-<1-(phenylsulfonyl)-3-(bromomethyl)indol-2-yl>acrylate
• 英文别名: ethyl (E)-3-[1-(benzenesulfonyl)-3-(bromomethyl)indol-2-yl]prop-2-enoate
• CAS: 958238-20-5
• 化学式: C₂₀H₁₈BrNO₄S
• 分子量: 448.337
• InChiKey: XGELHNZSFYKSBL-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 3'-<1-(phenylsulfonyl)-3-(bromomethyl)indol-2-yl>acrylate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-(β-Carbethoxyvinyl)-1-(phenylsulfonyl)-3-<β'-(6'-nitroveratryl)vinyl>indole
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.

  DOI：

  10.1021/jo00112a011
• 作为产物：
  描述：

  1-(苯磺酰基)-3-甲基吲哚-2-甲醛 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 Ethyl 3'-<1-(phenylsulfonyl)-3-(bromomethyl)indol-2-yl>acrylate
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.

  DOI：

  10.1021/jo00112a011

文献信息

• A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (−)-16-Episilicine
  作者：Mercedes Amat、Núria Llor、Begoña Checa、Elies Molins、Joan Bosch

  DOI：10.1021/jo902346j

  日期：2010.1.1

  Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantioselective total synthesis of an alkaloid of the silicine group.

  从合适的不饱和苯基甘醇衍生的恶唑并哌啶酮内酰胺开始，据报道合成了（-）-16-哌啶子碱，关键步骤是立体选择性共轭加成，立体选择性烷基化和闭环易位反应。这代表了硅基生物碱的第一个对映选择性全合成。
• 10.1021/acs.joc.4c00571
  作者：Agneswaran, Rudrasenan、Mohanakrishnan, Arasambattu K.

  DOI：10.1021/acs.joc.4c00571

  日期：——

  In this study, we present our findings on the synthesis of α-, β-, γ-carbolines via PIFA/BF3·OEt2-mediated intramolecular cyclization of isomeric azidomethyl(indolyl)acrylates. Alternately, 1,5,7-triazabicyclo[4.4.0]dec-5-ene/1,8-diazabicyclo(5.4.0)undec-7-ene (TBD/DBU)-mediated Michael addition followed by intramolecular cyclization of isomeric 2/3-(azidomethyl)indol-3/2-yl)acrylates also furnished

  在本研究中，我们展示了通过 PIFA/BF 3 ·OEt 2介导的异构叠氮甲基（吲哚基）丙烯酸酯的分子内环化合成 α-、β-、γ-咔啉的研究结果。或者，1,5,7-三氮杂双环[4.4.0]dec-5-ene/1,8-二氮杂双环(5.4.0)十一碳-7-烯 (TBD/DBU) 介导的迈克尔加成，然后进行异构体的分子内环化2/3-(叠氮甲基)吲哚-3/2-基)丙烯酸酯还提供了各自的β-和γ-咔啉衍生物。出乎意料的是，2-(叠氮基甲基)-3-(吲哚-3-基)丙烯酸酯的热解导致通过氮宾插入和重排形成5-(2-(苯基磺酰胺基)芳基)烟酸乙酯以及γ-咔啉和环化。异构2-(叠氮基甲基)-3-(吲哚-2-基)丙烯酸酯热解后产生预期的δ-咔啉。热分子内氮烯插入反应也可以扩展到获得吡啶并苯并噻吩、吡啶并噻吩和喹啉。
• Synthesis of N-protected indolaldehydes using modified Hass procedure
  作者：Ramalingam Balamurugan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2007.08.035

  日期：2007.11

  A detailed study on oxidation of N-protected bromomethylindoles into the respective aldehydes was carried out. Using a modified Hass procedure, synthesis of aryl-/hetero-aryl aldehydes in particular indolaldehydes is achieved in reasonable yields. (c) 2007 Elsevier Ltd. All rights reserved.
• A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder
  作者：Arasambattu K. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1021/jo00112a011

  日期：1995.4

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.