1,3-dibromoazulen-2-yllithium

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,3-dibromoazulen-2-yllithium
• 化学式: C₁₀H₅Br₂Li
• 分子量: 291.899
• InChiKey: LGWGGNIKNRBVBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-dibromoazulen-2-yllithium 在 碘 作用下， 以 四氢呋喃 为溶剂， 生成 1,3-dibromo-2-iodoazulene
  参考文献：
  名称：

  Synthesis and Structural Characterization of Diazulenylborinic Acid

  摘要：

  Diazulenylborinic acid 1 was synthesized by the reaction of 1,3-dibromoazulen-2-yllithium (2) with 1,3-dibromoazulen-2-ylboronic acid ethylene glycol ester (7d). The X-Ray crystallographic study of 1 revealed that it forms a dimeric structure through intermolecular hydrogen bonding between the hydroxyl groups. To obtain the tetracoordinate borinate derivative from 1, the attempted esterification of 1 with N,N-dimethylethanolamine did not give corresponding borinate 8 but resulted in the unexpected protodeboronation to give parent 1,3-dibromoazulene (4). The C-13 and B-11 NMR. studies of 1 in the presence of Et3N revealed the change in the pi-polarization of the azulenyl group accompanied by the change in the geometry of the boron to a tetracoordinate structure.

  DOI：

  10.3987/com-17-13651
• 作为产物：
  描述：

  奥苷菊环 在 N-溴代丁二酰亚胺(NBS) 、 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 为溶剂， 生成 1,3-dibromoazulen-2-yllithium
  参考文献：
  名称：

  Synthesis and Structural Characterization of Diazulenylborinic Acid

  摘要：

  Diazulenylborinic acid 1 was synthesized by the reaction of 1,3-dibromoazulen-2-yllithium (2) with 1,3-dibromoazulen-2-ylboronic acid ethylene glycol ester (7d). The X-Ray crystallographic study of 1 revealed that it forms a dimeric structure through intermolecular hydrogen bonding between the hydroxyl groups. To obtain the tetracoordinate borinate derivative from 1, the attempted esterification of 1 with N,N-dimethylethanolamine did not give corresponding borinate 8 but resulted in the unexpected protodeboronation to give parent 1,3-dibromoazulene (4). The C-13 and B-11 NMR. studies of 1 in the presence of Et3N revealed the change in the pi-polarization of the azulenyl group accompanied by the change in the geometry of the boron to a tetracoordinate structure.

  DOI：

  10.3987/com-17-13651

文献信息

• Synthesis and Structural Characterization of Diazulenylborinic Acid
  作者：Toshihiro Murafuji、Kohhei Shintaku、Kouhei Nagao、Yuji Mikata、Katsuya Ishiguro、Shin Kamijo

  DOI：10.3987/com-17-13651

  日期：——

  Diazulenylborinic acid 1 was synthesized by the reaction of 1,3-dibromoazulen-2-yllithium (2) with 1,3-dibromoazulen-2-ylboronic acid ethylene glycol ester (7d). The X-Ray crystallographic study of 1 revealed that it forms a dimeric structure through intermolecular hydrogen bonding between the hydroxyl groups. To obtain the tetracoordinate borinate derivative from 1, the attempted esterification of 1 with N,N-dimethylethanolamine did not give corresponding borinate 8 but resulted in the unexpected protodeboronation to give parent 1,3-dibromoazulene (4). The C-13 and B-11 NMR. studies of 1 in the presence of Et3N revealed the change in the pi-polarization of the azulenyl group accompanied by the change in the geometry of the boron to a tetracoordinate structure.