11-methoxy-6H,7H-<1>benzopyrano<4,3-b><1>benzopyran-6,7-dione

• 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: 11-methoxy-6H,7H-<1>benzopyrano<4,3-b><1>benzopyran-6,7-dione
• 英文别名: frutinone C methyl ether；11-methoxy-6H,7H-[1]benzopyrano[4,3-b][1]benzopyran-6,7-dione；11-methoxychromeno[4,3-b]chromene-6,7-dione
• 化学式: C₁₇H₁₀O₅
• 分子量: 294.263
• InChiKey: AXYBJQAAIMMOIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.65
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-乙炔基-2-(甲氧基甲氧基)苯 在 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 三丁基膦 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 80.0 ℃ 、5.07 MPa 条件下， 反应 22.5h， 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

文献信息

• A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives
  作者：Kang Lei、Dong-Wei Sun、Yuan-Yuan Tao、Xiao-Hua Xu

  DOI：10.1071/ch15267

  日期：——

  A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2′-hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker–Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then

  通过使用廉价的2'-羟基苯乙酮作为起始原料，分三步完成了天然产物果胶酮A的全合成新方案。关键中间体3-（2-氯苯甲酰基）-4-羟基香豆素是通过2-氯苯基2-乙酰基苯基的Baker-Venkataraman重排反应，然后在碱性条件下引入氯甲酸甲酯在一个罐中合成的。然后，碱促进的3-（2-氯苯甲酰基）-4-羟基香豆素的分子内亲核取代反应以优异的产率提供了果丁酮A。合成路线具有高收率，无过渡金属和温和的反应条件，以及对功能性的高度耐受性，因此可以在果胶酮A核周围轻松取代。
• New chromonocoumarin (=6H, 7H-[1]Benzopyrano[4,3-b][1]benzopyran-6,7-dione) derivatives fromPolygala fruticosa BERG
  作者：Ermindo R. Di Paolo、Matthias O. Hamburger、Helen Stoeckli-Evans、Colin Rogers、Kurt Hostettmann

  DOI：10.1002/hlca.19890720705

  日期：1989.11.1

  Three chromonocoumarins ( =6H, 7H-[1]benzopyrano[4,3-b][1]benzopyran-6,7-diones) 1–3 have been isolated from the leaves and the root bark of polygala fruticosa BERG. (syn. Polygala oppositifoliaL.; Polygalaceae). The structure of frutinone A (1) was established by X-ray diffraction analysis. The structures of the previously undescribed compounds frutinone B (2) and C (3) were deduced by spectroscopic

  从远志叶BERG BERG的叶子和根皮中分离出3个色氨酸香豆素（= 6 H，7 H- [1]苯并吡喃并[4,3- b ] [1]苯并吡喃-6,7-二酮）1-3。（syn.Polygala oppositifolia L .； Polygalaceae）。通过X射线衍射分析确定了品丁酮A（1）的结构。通过光谱方法（EI-MS，UV，IR，1 H和13 C-NMR，包括NOE和COSY）推导了先前未描述的化合物frutinone B（2）和C（3）的结构，与1。色香豆素1-3是新型天然化合物的首批代表。Frutinone A对黄瓜刺柏（Cladosporium cucumerinum）表现出较强的杀真菌活性。
• DI, PAOLO ERMINDO R.;HAMBURGER, MATTHIAS O.;STOECKLI-EVANS, HELEN;ROGERS,+, HELV. CHIM. ACTA, 72,(1989) N, C. 1455-1462
  作者：DI, PAOLO ERMINDO R.、HAMBURGER, MATTHIAS O.、STOECKLI-EVANS, HELEN、ROGERS,+

  DOI：——

  日期：——
• 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.