N-[(3-bromothiophen-2-yl)methylene]cyclohexanamine | 1609732-26-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: N-[(3-bromothiophen-2-yl)methylene]cyclohexanamine
• 英文别名: 1-(3-bromothiophen-2-yl)-N-cyclohexylmethanimine
• CAS: 1609732-26-4
• 化学式: C₁₁H₁₄BrNS
• 分子量: 272.209
• InChiKey: JXBZQJSEZNLGMT-UHFFFAOYSA-N

物化性质

• 沸点：
  349.4±27.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(3-bromothiophen-2-yl)methylene]cyclohexanamine 在 正丁基锂 、 噻吩-2-甲酸亚铜(I) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 为溶剂， 反应 62.67h， 生成 5-(trimethylsilyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Comparison of Ullmann/RCM and Ullmann/Bis-hydrazone Coupling Reactions; New Access to Benzodithiophenes for Dye-Sensitized Solar Cell and Thiahelicene Applications

  摘要：

  The use of CuTC (Liebeskind's catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This approach establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer, which has previously been underused in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.

  DOI：

  10.1055/s-0033-1340667
• 作为产物：
  描述：

  3-溴噻吩-2-甲醛 、 环己胺 以 甲苯 为溶剂， 反应 16.0h， 以100%的产率得到N-[(3-bromothiophen-2-yl)methylene]cyclohexanamine
  参考文献：
  名称：

  Comparison of Ullmann/RCM and Ullmann/Bis-hydrazone Coupling Reactions; New Access to Benzodithiophenes for Dye-Sensitized Solar Cell and Thiahelicene Applications

  摘要：

  The use of CuTC (Liebeskind's catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This approach establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer, which has previously been underused in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.

  DOI：

  10.1055/s-0033-1340667