6-(2'-(2'',4''-diacetoxyphenyl)ethynyl)-1-methoxy-3,4-methylenedioxybenzene | 673477-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 6-(2'-(2'',4''-diacetoxyphenyl)ethynyl)-1-methoxy-3,4-methylenedioxybenzene
• 英文别名: 1-(2-methoxy-4,5-methylenedioxyphenyl)-2-(2,4-diacetoxyphenyl)ethyne；[3-Acetyloxy-4-[2-(6-methoxy-1,3-benzodioxol-5-yl)ethynyl]phenyl] acetate；[3-acetyloxy-4-[2-(6-methoxy-1,3-benzodioxol-5-yl)ethynyl]phenyl] acetate
• CAS: 673477-44-6
• 化学式: C₂₀H₁₆O₇
• 分子量: 368.343
• InChiKey: FZSKMOAUNAXRIP-UHFFFAOYSA-N

物化性质

• 沸点：
  516.5±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(2'-(2'',4''-diacetoxyphenyl)ethynyl)-1-methoxy-3,4-methylenedioxybenzene 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以36%的产率得到2-(2'-methoxy-4',5'-methylenedioxyphenyl)-6-hydroxybenzofuran
  参考文献：
  名称：

  The first total synthesis of Cicerfuran utilizing a one-pot synthesis of hydroxylated benzofurans

  摘要：

  A simple one-pot procedure was elaborated for the preparation of hydroxylated benzofurans from halogenated phenols and was successfully applied to the first total synthesis of Cicerfuran, a natural defence agent of wild chickpea. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01170-0
• 作为产物：
  描述：

  芝麻酚 在 palladium diacetate bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 溴 、 溶剂黄146 、 二异丙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 50.08h， 生成 6-(2'-(2'',4''-diacetoxyphenyl)ethynyl)-1-methoxy-3,4-methylenedioxybenzene
  参考文献：
  名称：

  The first total synthesis of Cicerfuran utilizing a one-pot synthesis of hydroxylated benzofurans

  摘要：

  A simple one-pot procedure was elaborated for the preparation of hydroxylated benzofurans from halogenated phenols and was successfully applied to the first total synthesis of Cicerfuran, a natural defence agent of wild chickpea. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01170-0

文献信息

• Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues
  作者：Shazia N. Aslam、Philip C. Stevenson、Sara J. Phythian、Nigel C. Veitch、David R. Hall

  DOI：10.1016/j.tet.2006.02.015

  日期：2006.4

  Routes were investigated for the synthesis of cicerfuran, a hydroxylated benzofuran from wild chickpea implicated in resistance to Fusarium wilt, and some of its analogues. A novel method is described for the synthesis of oxygenated benzofurans by epoxidation and cyclisation of 2′-hydroxystilbenes. The stilbene intermediates required could be synthesised by palladium-catalysed coupling of styrenes

  研究了从野生鹰嘴豆中合成羟基化的苯并呋喃类化合物cicerfuran的途径，其中涉及抗枯萎病枯萎病及其一些类似物。描述了一种新的方法，用于通过2'-羟基苯乙烯的环氧化和环化合成氧化的苯并呋喃。所需的二苯乙烯中间体可以通过钯催化的苯乙烯与单加氧的芳基卤化物而不是与二加氧的芳基卤化物偶合而合成。通过维蒂希反应合成了对应于后者的二苯乙烯。
• The first total synthesis of Cicerfuran utilizing a one-pot synthesis of hydroxylated benzofurans
  作者：Zoltán Novák、Géza Timári、András Kotschy

  DOI：10.1016/s0040-4020(03)01170-0

  日期：2003.9

  A simple one-pot procedure was elaborated for the preparation of hydroxylated benzofurans from halogenated phenols and was successfully applied to the first total synthesis of Cicerfuran, a natural defence agent of wild chickpea. (C) 2003 Elsevier Ltd. All rights reserved.