trans-1,4-bis(bromoethynyl)cyclohexa-2,5-diene-1,4-diol | 852992-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1,4-bis(bromoethynyl)cyclohexa-2,5-diene-1,4-diol
• CAS: 852992-25-7
• 化学式: C₁₀H₆Br₂O₂
• 分子量: 317.964
• InChiKey: IFKOKROYSVORBD-MGCOHNPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-1,4-bis(bromoethynyl)cyclohexa-2,5-diene-1,4-diol 在 哌啶 、 正丁基锂 、 盐酸羟胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 4.25h， 生成 2,5-bis(phenylbutadiynyl)oxepin
  参考文献：
  名称：

  Synthesis of 2,5-diethynyl substituted oxepins from trans-1,4-diethynylcyclohexa-2,5-diene-1,4-diols

  摘要：

  Reaction of trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4-diol with n-BuLi followed by methanesulfonyl chloride resulted in the formation of a dark red solid, which was identified as 2,5-bis(trimethylsilylethynyl)oxepin. Deprotection of the silyl groups resulted in the formation of 2,5-diethynyloxepin, a red, shock sensitive solid. Reaction of a differentially substituted cyclohexa-2,5-diene-1,4-diol gave a mixture of 2,5-diethynyl substituted oxepins. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.044
• 作为产物：
  描述：

  1,4-diethynylcyclohexa-2,5-diene-1,4-diol 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 0.75h， 以94%的产率得到trans-1,4-bis(bromoethynyl)cyclohexa-2,5-diene-1,4-diol
  参考文献：
  名称：

  Synthesis of 2,5-diethynyl substituted oxepins from trans-1,4-diethynylcyclohexa-2,5-diene-1,4-diols

  摘要：

  Reaction of trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4-diol with n-BuLi followed by methanesulfonyl chloride resulted in the formation of a dark red solid, which was identified as 2,5-bis(trimethylsilylethynyl)oxepin. Deprotection of the silyl groups resulted in the formation of 2,5-diethynyloxepin, a red, shock sensitive solid. Reaction of a differentially substituted cyclohexa-2,5-diene-1,4-diol gave a mixture of 2,5-diethynyl substituted oxepins. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.044