1-(3'-hydroxy-3'-methylbutyn-1'-yl)-2-methoxy-4,5-methylenedioxybenzene | 673477-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(3'-hydroxy-3'-methylbutyn-1'-yl)-2-methoxy-4,5-methylenedioxybenzene
• 英文别名: 4-(6-Methoxy-1,3-benzodioxol-5-yl)-2-methylbut-3-yn-2-ol
• CAS: 673477-42-4
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: LEWJWFCSQLHKBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3'-hydroxy-3'-methylbutyn-1'-yl)-2-methoxy-4,5-methylenedioxybenzene 在 氢氧化钾 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以84%的产率得到1-ethynyl-2-methoxy-4,5-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
• 作为产物：
  描述：

  5-溴-6-羟基-1,3-苯并二恶茂,2-溴-4,5-亚甲基二氧苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 二异丙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 1-(3'-hydroxy-3'-methylbutyn-1'-yl)-2-methoxy-4,5-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

• Simple, Convenient, and Efficient Synthesis of 2-Aryl-substituted Benzo[b]furans
  作者：Yong Jiang、Botao Gao、Wenjuan Huang、Yongmin Liang、Guosheng Huang、Yongxiang Ma

  DOI：10.1080/00397910701860323

  日期：2008.12.31

  convenient, and efficient one-pot method for the preparation of benzofuran is reported. Sonogashira coupling reaction of aryl iodides with 2-methyl-3-butyn-2-ol was used as an acetylene source in the presence of Pd(PPh3)2Cl2 and CuI. Deprotection of the acetylene moiety in the same pot using a strong base and the second Sonogashira coupling/cyclization of and substituted o-iodophenols led to the formation

  摘要 报道了一种简单、方便、高效的一锅法制备苯并呋喃。在 Pd(PPh3)2Cl2 和 CuI 存在下，芳基碘化物与 2-methyl-3-butyn-2-ol 的 Sonogashira 偶联反应用作乙炔源。在同一锅中使用强碱对乙炔部分进行脱保护，并与取代的邻碘苯酚进行第二次 Sonogashira 偶联/环化，导致形成适当的苯并 [b] 呋喃。这些协议也可用于合成天然产物和吲哚。
• 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.