methyl 2-[2-(methoxymethoxy)phenyl]-8-(oxan-2-yloxy)-4-oxo-4H-chromene-3-carboxylate | 1607814-79-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: methyl 2-[2-(methoxymethoxy)phenyl]-8-(oxan-2-yloxy)-4-oxo-4H-chromene-3-carboxylate
• 英文别名: Methyl 2-[2-(methoxymethoxy)phenyl]-8-(oxan-2-yloxy)-4-oxochromene-3-carboxylate；methyl 2-[2-(methoxymethoxy)phenyl]-8-(oxan-2-yloxy)-4-oxochromene-3-carboxylate
• CAS: 1607814-79-8
• 化学式: C₂₄H₂₄O₈
• 分子量: 440.45
• InChiKey: JXTUCPUTIQCSIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-[2-(methoxymethoxy)phenyl]-8-(oxan-2-yloxy)-4-oxo-4H-chromene-3-carboxylate 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 8.0h， 生成 11-methoxy-6H,7H-<1>benzopyrano<4,3-b><1>benzopyran-6,7-dione
  参考文献：
  名称：

  A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

  摘要：

  A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.073
• 作为产物：
  描述：

  1-乙炔基-2-(甲氧基甲氧基)苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 三丁基膦 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 30.0~80.0 ℃ 、5.07 MPa 条件下， 反应 14.5h， 生成 methyl 2-[2-(methoxymethoxy)phenyl]-8-(oxan-2-yloxy)-4-oxo-4H-chromene-3-carboxylate
  参考文献：
  名称：

  A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

  摘要：

  A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.073

文献信息

• A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization
  作者：Masahito Yoshida、Koya Saito、Yuta Fujino、Takayuki Doi

  DOI：10.1016/j.tet.2014.03.073

  日期：2014.5

  A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c). (C) 2014 Elsevier Ltd. All rights reserved.