5-(3,5-dibromobenzo[b]furan-2-yl)benzo[1,3]dioxole | 365448-16-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-(3,5-dibromobenzo[b]furan-2-yl)benzo[1,3]dioxole
• 英文别名: 5-(3,5-Dibromo-1-benzofuran-2-yl)-1,3-benzodioxole
• CAS: 365448-16-4
• 化学式: C₁₅H₈Br₂O₃
• 分子量: 396.035
• InChiKey: CAXYQINJOONIEY-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C
• 沸点：
  461.1±45.0 °C(Predicted)
• 密度：
  1.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3,5-dibromobenzo[b]furan-2-yl)benzo[1,3]dioxole 在 1,2-双(二苯基膦)乙烷氯化镍 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.17h， 生成 5-[3-甲基-5-(1-丙烯-1-基)-1-苯并呋喃-2-基]-1,3-苯并二氧戊环
  参考文献：
  名称：

  Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions

  摘要：

  Six different eupomatenoids (1a-c, 1f-h) were prepared from 2,3,5-tribroinobenzofuran (2) in a concise and high-yielding synthetic sequence. The overall yields vary between 29 and 60% over four to six steps. Key to the success of the syntheses is the high regioselectivity achieved in three Pd(0)- and Ni(0)-catalyzed cross-coupling reactions which were conducted consecutively. The order of substitution at the benzofuran nucleus is C-2, C-5 and C-3. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02287-6
• 作为产物：
  描述：

  2,3,5-tribromo-2,3-dihydrobenzofuran 在 氢氧化钾 、 溴 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 38.17h， 生成 5-(3,5-dibromobenzo[b]furan-2-yl)benzo[1,3]dioxole
  参考文献：
  名称：

  Bach, Thorsten; Bartels, Marc, Synthesis, 2003, # 6, p. 925 - 939

  摘要：

  DOI：

文献信息

• 2,3-Disubstituted and 2,3,5-Trisubstituted Benzofurans by Regioselective Pd-Catalyzed Cross-coupling Reactions; a Short Synthesis of Eupomatenoid-15
  作者：Thorsten Bach、Marc Bartels

  DOI：10.1055/s-2001-16052

  日期：——

  2,3-Dibromobenzofuran (1) and 2,3,5-tribromobenzofuran (2) undergo regioselective Sonogashira- and Negishi-type cross-coupling reactions at the 2-position. Subsequent substitution reactions at C-3 are possible for the cross-coupling products obtained from compound 1. A regioselective functionalization of the 3,5-dibromobenzofurans derived from substrate 2 was achieved by an halogen-metal exchange which occurred selectively at the 3-position. In a conclusive reaction step cross-coupling reactions at C-5 were used to build up 2,3,5-trisubstituted benzofurans. As an example, the synthesis of eupomatenoid-15 (8) is described.

  2,3-二溴苯并呋喃（1）和2,3,5-三溴苯并呋喃（2）在2-位点进行区域选择性的Sonogashira型和Negishi型交叉偶联反应。从化合物1得到的交叉偶联产物在C-3位可以进行后续取代反应。通过对2来自底物2的3,5-二溴苯并呋喃进行区域选择性功能化，实现了在3-位点选择性发生卤素-金属交换。在最终的反应步骤中，利用C-5位的交叉偶联反应构建了2,3,5-三取代的苯并呋喃。作为一个例子，描述了eupomatenoid-15（8）的合成。
• Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions
  作者：Thorsten Bach、Marc Bartels

  DOI：10.1016/s0040-4039(02)02287-6

  日期：2002.12

  Six different eupomatenoids (1a-c, 1f-h) were prepared from 2,3,5-tribroinobenzofuran (2) in a concise and high-yielding synthetic sequence. The overall yields vary between 29 and 60% over four to six steps. Key to the success of the syntheses is the high regioselectivity achieved in three Pd(0)- and Ni(0)-catalyzed cross-coupling reactions which were conducted consecutively. The order of substitution at the benzofuran nucleus is C-2, C-5 and C-3. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Bach, Thorsten; Bartels, Marc, Synthesis, 2003, # 6, p. 925 - 939
  作者：Bach, Thorsten、Bartels, Marc

  DOI：——

  日期：——