2-(2-nitrophenyl)-2-cyclohepten-1-one | 443303-79-5

• 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: 2-(2-nitrophenyl)-2-cyclohepten-1-one
• 英文别名: 2-(2-Nitrophenyl)cyclohept-2-en-1-one
• CAS: 443303-79-5
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: IWKYHWALKDCIRR-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  418.0±45.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-nitrophenyl)-2-cyclohepten-1-one 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 1,10-菲罗啉 、 一氧化碳 、 1,3-双(二苯基膦)丙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、607.95 kPa 条件下， 以66%的产率得到环庚三烯并[b]吲哚-10(5H)-酮,6,7,8,9-四氢-
  参考文献：
  名称：

  Novel palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones

  摘要：

  Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to carbazolones, an intermolecular Stille coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation. A number of functionalized 1,2-dihydro-4(3H)-carbazolones were prepared using this sequence. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00072-2
• 作为产物：
  描述：

  2-iodocyclohept-2-en-1-one 、 tributyl(2-nitrophenyl)stannane 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三苯胂 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 72.0h， 以68%的产率得到2-(2-nitrophenyl)-2-cyclohepten-1-one
  参考文献：
  名称：

  Palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones. Formal total synthesis of murrayaquinone A

  摘要：

  Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to 1,2-dihydro-4(3H)-carbazolones. The steps are an intermolecular Stille cross-coupling followed by a reductive N-heteroannulation. A formal total synthesis of murrayaquinone A, employing this sequence, is reported. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)00976-1

文献信息

• Synthesis of 1,2,3,4-tetrahydrocarbazoles and related tricyclic indoles
  作者：Tricia L. Scott、Nicholas Burke、Grissell Carrero-Martínez、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2006.11.052

  日期：2007.1

  Reduction of 2-(2-nitrophenyl)-2-cyclohexene-1-ones using palladium on carbon under 1 atm of hydrogen gas at ambient temperature affords 1,2,3,4-tetrahydrocarbazoles in excellent isolated yields. The starting materials were prepared by intermolecular Stille coupling of 2-iodo-2-cyclohexen-1-ones with 2-(tributylstannyl)-1-nitrobenzenes.

  在室温下在氢气中，在1个大气压下，使用钯碳还原2-（2-硝基苯基）-2-环己烯-1-酮，可得到1,2,3,4-四氢咔唑，分离产率极佳。通过2-碘-2-环己烯-1-酮与2-（三丁基锡烷基）-1-硝基苯的分子间Stille偶联制备起始原料。
• Synthesis of Indoles via Palladium[0]-Mediated Ullmann Cross-Coupling of <i>o-</i>Halonitroarenes with α-Halo-enones or -enals
  作者：Martin G. Banwell、Brian D. Kelly、Okanya J. Kokas、David W. Lupton

  DOI：10.1021/ol034745w

  日期：2003.7.1

  [reaction: see text] Palladium[0]-mediated Ullmann cross-coupling of o-halonitrobenzene (1) and various related nitroarenes with a range of alpha-halo-enones (e.g., 2) or -enals readily affords the expected alpha-arylenones, e.g., 3, or -enals, which are converted into the corresponding indoles, e.g., 4, on reaction with dihydrogen in the presence of Pd on C.

  [反应：请参阅文本]钯[0]介导的邻卤代硝基苯（1）与各种相关硝基芳烃与一系列α-卤代烯酮（例如2）或-烯醛的Ullmann交叉偶合可轻松提供预期的α-丙烯酮（例如3或-烯醛）在C上存在Pd时与二氢反应时转化为相应的吲哚（例如4）。
• [EN] A METHOD OF INDOLE SYNTHESIS<br/>[FR] PROCEDE DE SYNTHESE D'INDOLE
  申请人：UNIV AUSTRALIAN

  公开号：WO2004096766A1

  公开（公告）日：2004-11-11

  The present invention relates to methods for the synthesis of indoles. In particular, the invention relates to the coupling of an a-haloenone or a-haloenal with an ortho-halonitroarene to form an ortho-(enone)nitroarene or ortho-(enal)nitroarene. Reductive cyclization of an ortho-(enone)nitroarene or ortho-(enal)nitroarene affords access to indole compounds.

  本发明涉及吲哚的合成方法。具体而言，该发明涉及将α-卤代酮或α-卤代烯醇与邻位卤代硝基芳烃偶联，形成邻位-(酮)硝基芳烃或邻位-(烯醛)硝基芳烃。对邻位-(酮)硝基芳烃或邻位-(烯醛)硝基芳烃进行还原环化，可获得吲哚化合物。
• Palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones. Formal total synthesis of murrayaquinone A
  作者：Tricia L Scott、Björn C.G Söderberg

  DOI：10.1016/s0040-4020(03)00976-1

  日期：2003.8

  Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to 1,2-dihydro-4(3H)-carbazolones. The steps are an intermolecular Stille cross-coupling followed by a reductive N-heteroannulation. A formal total synthesis of murrayaquinone A, employing this sequence, is reported. (C) 2003 Elsevier Ltd. All fights reserved.
• Novel palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones
  作者：Tricia L. Scott、Björn C.G. Söderberg

  DOI：10.1016/s0040-4039(02)00072-2

  日期：2002.2

  Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to carbazolones, an intermolecular Stille coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation. A number of functionalized 1,2-dihydro-4(3H)-carbazolones were prepared using this sequence. (C) 2002 Elsevier Science Ltd. All rights reserved.