1-bromo-5,10-dioxatridec-12-ene-2,7-diyne | 769136-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-5,10-dioxatridec-12-ene-2,7-diyne
• 英文别名: 1-(4-Bromobut-2-ynoxy)-4-prop-2-enoxybut-2-yne
• CAS: 769136-05-2
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: UPOIJKSKMITGJW-UHFFFAOYSA-N

物化性质

• 沸点：
  327.5±37.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-bis-endo-dihydroxy-bicyclo[2.2.1]hept-2-ene 、 1-bromo-5,10-dioxatridec-12-ene-2,7-diyne 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以96%的产率得到
  参考文献：
  名称：

  Ene–yne metathesis of polyunsaturated norbornene derivatives

  摘要：

  Norbornene derivatives bearing endo-substituents in the 5- and 6-positions were studied as substrates for ene-yne metathesis cascades. Substrates which contained an internal alkyne and a terminal alkene or alkyne in each sidechain were found to undergo a metathesis cascade leading to pentacyclic bis-dienes and bis-trienes. Attempts to extend the chemistry further to sidechains containing two internal alkynes or two internal alkynes and a terminal alkene were not successful with the first generation Grubbs' catalyst. However, the substrate containing two internal alkynes did react with the second generation Grubbs' catalyst to give a tetra-diene containing product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.114
• 作为产物：
  描述：

  4-(allyloxy)but-2-yn-1-ol 在 氢氧化钾 、 四溴化碳 、 二甲基亚砜 、 三苯基膦 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 1-bromo-5,10-dioxatridec-12-ene-2,7-diyne
  参考文献：
  名称：

  Ene–yne metathesis of polyunsaturated norbornene derivatives

  摘要：

  Norbornene derivatives bearing endo-substituents in the 5- and 6-positions were studied as substrates for ene-yne metathesis cascades. Substrates which contained an internal alkyne and a terminal alkene or alkyne in each sidechain were found to undergo a metathesis cascade leading to pentacyclic bis-dienes and bis-trienes. Attempts to extend the chemistry further to sidechains containing two internal alkynes or two internal alkynes and a terminal alkene were not successful with the first generation Grubbs' catalyst. However, the substrate containing two internal alkynes did react with the second generation Grubbs' catalyst to give a tetra-diene containing product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.114