5-methyl-3-(6-nitro-1,3-benzodioxol-5-yl)-2-cyclohexen-1-one | 916602-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-methyl-3-(6-nitro-1,3-benzodioxol-5-yl)-2-cyclohexen-1-one
• 英文别名: 5-Methyl-3-(6-nitro-1,3-benzodioxol-5-yl)cyclohex-2-en-1-one；5-methyl-3-(6-nitro-1,3-benzodioxol-5-yl)cyclohex-2-en-1-one
• CAS: 916602-02-3
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: KTCKJOGBWBKITG-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  426.9±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(6-nitro-1,3-benzodioxol-5-yl)-2-cyclohexen-1-one 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 一氧化碳 、 1,3-双(二苯基膦)丙烷 、 邻菲罗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 80.0~90.0 ℃ 、607.95 kPa 条件下， 反应 24.0h， 以100%的产率得到3-methyl-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  Palladium-catalyzed syntheses of tetrahydrocarbazolones as advanced intermediates to carbazole alkaloids

  摘要：

  Two sequential palladium-catalyzed reactions, an intermolecular Stille cross-coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation, have been employed as the key synthetic steps toward six tetrahydrocarbazolones. The products are advanced intermediates toward a number of naturally occurring carbazole alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.100
• 作为产物：
  描述：

  5-甲基环己烷-1,3-二酮 在 二(氰基苯)二氯化钯 copper(l) iodide 、 三苯胂 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 、 乙腈 为溶剂， 反应 384.0h， 生成 5-methyl-3-(6-nitro-1,3-benzodioxol-5-yl)-2-cyclohexen-1-one
  参考文献：
  名称：

  Palladium-catalyzed syntheses of tetrahydrocarbazolones as advanced intermediates to carbazole alkaloids

  摘要：

  Two sequential palladium-catalyzed reactions, an intermolecular Stille cross-coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation, have been employed as the key synthetic steps toward six tetrahydrocarbazolones. The products are advanced intermediates toward a number of naturally occurring carbazole alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.100

文献信息

• Palladium-catalyzed syntheses of tetrahydrocarbazolones as advanced intermediates to carbazole alkaloids
  作者：Tricia L. Scott、Xiaomei Yu、Sobha P. Gorugantula、Grissell Carrero-Martínez、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2006.08.100

  日期：2006.11

  Two sequential palladium-catalyzed reactions, an intermolecular Stille cross-coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation, have been employed as the key synthetic steps toward six tetrahydrocarbazolones. The products are advanced intermediates toward a number of naturally occurring carbazole alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.