5,7-dimethoxy-3-[9-(5-methylfuran-2-yl)nonyl]-3H-2-benzofuran-1-one | 743427-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5,7-dimethoxy-3-[9-(5-methylfuran-2-yl)nonyl]-3H-2-benzofuran-1-one
• CAS: 743427-16-9
• 化学式: C₂₄H₃₂O₅
• 分子量: 400.515
• InChiKey: TWBXWPXSOAXUBM-UHFFFAOYSA-N

物化性质

• 沸点：
  549.0±50.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-3-[9-(5-methylfuran-2-yl)nonyl]-3H-2-benzofuran-1-one 在 硫酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以98%的产率得到14-(1,3-dihydro-4,6-dimethoxy-3-oxo-1-isobenzofuranyl)-2,5-tetradecanedione
  参考文献：
  名称：

  Synthesis of a new microbial secondary metabolite: anti- Helicobacter pylori CJ-13,015

  摘要：

  A six-step, first synthesis of an anti-Helicobacter pylori secondary metabolite, CJ-13,015 (1a), in 65% overall yield, is described, starting from 5-methylfurfural (2), via a Wittig reaction of the ylide generated in situ from (8-hydroxyoctyl)triphenylphosphonium bromide, selective reduction of the newly formed carbon-carbon double bond, conversion of the alcohol to a halide, coupling with the anion of 3,5-dimethoxyphthalide and a chemoselective conversion of the protective furan group to a 1,4-dicarbonyl system as a key reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.086
• 作为产物：
  描述：

  (8-hydroxyoctyl)triphenylphosphonium bromide 在 palladium on activated charcoal 4-二甲氨基吡啶 、 TEA 、 氢气 、 碳酸氢钠 、 dimsyl sodium 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 27.5h， 生成 5,7-dimethoxy-3-[9-(5-methylfuran-2-yl)nonyl]-3H-2-benzofuran-1-one
  参考文献：
  名称：

  Synthesis of a new microbial secondary metabolite: anti- Helicobacter pylori CJ-13,015

  摘要：

  A six-step, first synthesis of an anti-Helicobacter pylori secondary metabolite, CJ-13,015 (1a), in 65% overall yield, is described, starting from 5-methylfurfural (2), via a Wittig reaction of the ylide generated in situ from (8-hydroxyoctyl)triphenylphosphonium bromide, selective reduction of the newly formed carbon-carbon double bond, conversion of the alcohol to a halide, coupling with the anion of 3,5-dimethoxyphthalide and a chemoselective conversion of the protective furan group to a 1,4-dicarbonyl system as a key reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.086

文献信息

• Synthesis of a new microbial secondary metabolite: anti- Helicobacter pylori CJ-13,015
  作者：Mukulesh Mondal、Narshinha P. Argade

  DOI：10.1016/j.tetlet.2004.05.086

  日期：2004.7

  A six-step, first synthesis of an anti-Helicobacter pylori secondary metabolite, CJ-13,015 (1a), in 65% overall yield, is described, starting from 5-methylfurfural (2), via a Wittig reaction of the ylide generated in situ from (8-hydroxyoctyl)triphenylphosphonium bromide, selective reduction of the newly formed carbon-carbon double bond, conversion of the alcohol to a halide, coupling with the anion of 3,5-dimethoxyphthalide and a chemoselective conversion of the protective furan group to a 1,4-dicarbonyl system as a key reaction. (C) 2004 Elsevier Ltd. All rights reserved.