5-[3-bromo-5-(prop-1-enyl)benzo[b]furan-2-yl]benzo[1,3]dioxole | 489422-94-8

• 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-bromo-5-(prop-1-enyl)benzo[b]furan-2-yl]benzo[1,3]dioxole
• 英文别名: 5-(3-bromo-5-prop-1-enyl-1-benzofuran-2-yl)-1,3-benzodioxole
• CAS: 489422-94-8
• 化学式: C₁₈H₁₃BrO₃
• 分子量: 357.203
• InChiKey: SMOBNXVAUNLFPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.6
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  甲基锂 、 5-[3-bromo-5-(prop-1-enyl)benzo[b]furan-2-yl]benzo[1,3]dioxole 在 zinc(II) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 0.17h， 以64%的产率得到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-tribromobenzofuran 在 1,2-双(二苯基膦)乙烷氯化镍 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 5-[3-bromo-5-(prop-1-enyl)benzo[b]furan-2-yl]benzo[1,3]dioxole
  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

文献信息

• 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.