Frutinone B

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: Frutinone B
• 英文别名: 4-Methoxychromeno[4,3-b]chromene-6,7-dione
• 化学式: C₁₇H₁₀O₅
• 分子量: 294.263
• InChiKey: YEEPARQWBYNUDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-iodophenyl methyl carbonate 在 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 三丁基膦 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 80.0 ℃ 、5.07 MPa 条件下， 反应 13.25h， 生成 Frutinone B
  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

• Polyphenolic Glycosides and Oligosaccharide Multiesters from the Roots of <i>Polygala </i><i>d</i><i>almaisiana</i>
  作者：Satoko Kobayashi、Toshio Miyase、Hiroshi Noguchi

  DOI：10.1021/np010434n

  日期：2002.3.1

  Four new polyphenolic glycosides, dalmaisiones A-D (1-4), 16 new oligosaccharide multiesters, dalmaisioses A-P (5, 7-21), and one known tetrasaccharide multiester, reiniose G (6), were isolated from the roots of Polygala dalmaisiana. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.
• 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.