5-bromo-7-methoxy-2-bromobenzofuran | 515814-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-bromo-7-methoxy-2-bromobenzofuran
• 英文别名: 2,5-dibromo-7-methoxybenzofuran；2,5-dibromo-7-methoxy-1-benzofuran
• CAS: 515814-03-6
• 化学式: C₉H₆Br₂O₂
• 分子量: 305.953
• InChiKey: YONKMCNKNFHCID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-7-methoxy-2-bromobenzofuran 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 (E)-2-(4-benzyloxy-3-methoxyphenyl)-5-(carbethoxyethenyl)-7-methoxybenzofuran
  参考文献：
  名称：

  Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling

  摘要：

  Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.

  DOI：

  10.1021/jo020653t
• 作为产物：
  描述：

  5-溴-2-羟基-3-甲氧基苯甲醛 在 三溴化磷 作用下， 反应 5.0h， 生成 5-bromo-7-methoxy-2-bromobenzofuran
  参考文献：
  名称：

  Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling

  摘要：

  Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.

  DOI：

  10.1021/jo020653t

文献信息

• Synthesis and Cytotoxicity Studies of Bioactive Benzofurans from <i>Lavandula agustifolia</i> and Modified Synthesis of Ailanthoidol, Homoegonol, and Egonol
  作者：Aneesh Sivaraman、Jin Sook Kim、Dipesh S. Harmalkar、Kyoung ho Min、Joong-Won Park、Yongseok Choi、Kyungtae Kim、Kyeong Lee

  DOI：10.1021/acs.jnatprod.0c00697

  日期：2020.11.25

  naturally occurring lignans and neolignans, have attracted extensive synthetic efforts due to their useful biological activities and significant pharmacological potential. Herein, we report a general and efficient approach to divergent 2-arylbenzofurans through a one-pot synthesis of versatile 2-bromobenzofurans as key intermediates. Using this approach, the first total synthesis of a series of trisubstituted

  2-芳基/烷基苯并呋喃是天然存在的木脂素和新木脂素的一个重要亚类，由于其有用的生物活性和显着的药理潜力，已吸引了广泛的合成努力。在此，我们报告了一种通用且有效的方法，通过一锅法合成多功能 2-溴苯并呋喃作为关键中间体来生成发散的 2-芳基苯并呋喃。使用这种方法，首次全合成了一系列带有羟乙基单元的三取代和四取代苯并呋喃，包括从Lavandula agustifolia ( 1 – 3 ) 及其非天然衍生物 ( 4 – 8 ) 中分离的天然化合物)，完成。我们还报告了臭虫醇、高麦角醇和 egonol 的改进合成方法，可以对它们的衍生物进行不同的合成，以供未来探索。其中，代表性的酚类天然化合物2及其衍生物7和5在 MCF74、A549、PC3、HepG2 和 Hep3B 癌细胞系中诱导凋亡细胞死亡相关的聚（ADP-核糖）聚合酶 (PARP) 裂解。此外，肿瘤抑制蛋白 p53 也在 p53 野生型癌细胞中被诱导。
• A highly efficient TBAF-promoted intramolecular cyclization of gem-dibromoolefins for the synthesis of 2-bromobenzofurans(thiophenes)
  作者：Wei Chen、Yicheng Zhang、Lei Zhang、Min Wang、Lei Wang

  DOI：10.1039/c1cc13967c

  日期：——

  A highly efficient tetra-(n-butyl)ammonium fluoride (TBAF)-promoted intramolecular cyclization of gem-dibromoolefins has been developed for the synthesis of 2-bromobenzofused heterocycles. The reaction provides a convenient approach to 2-bromobenzofurans(thiophenes) from the corresponding readily available gem-dibromovinyl substrates without a metal.

  已经开发了一种高效的四（正丁基）氟化铵（TBAF）促进的宝石二溴代烯烃分子内环化反应，用于合成2-溴苯并稠合的杂环。该反应提供了从相应的容易获得的不含金属的宝石-二溴乙烯基底物中2-溴苯并呋喃（噻吩）的简便方法。
• Trace amount Cu (ppm)-catalyzed intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to 2-bromobenzofurans(thiophenes)
  作者：Yong Ji、Pinhua Li、Xiuli Zhang、Lei Wang

  DOI：10.1039/c3ob40531a

  日期：——

  An intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to give 2-bromobenzofurans(thiophenes) in the presence of a trace amount of Cu (0.0064 mol%, 25 ppm) has been developed. The reaction provides the desired products in excellent yields under fluoride-free and mild reaction conditions and with a TON (turnover number) of up to 1.5 × 104.

  在痕量铜（0.0064 mol%，25 ppm）存在下，开发了一种 2-(gem-dibromovinyl)苯酚（噻吩酚）分子内环化生成 2-溴苯并呋喃（噻吩）的方法。在无氟和温和的反应条件下，该反应能以极高的产率提供所需的产物，其 TON（转化率）高达 1.5 × 104。
• Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling
  作者：Shun-Yu Lin、Chih-Lung Chen、Yean-Jang Lee

  DOI：10.1021/jo020653t

  日期：2003.4.1

  Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.