(1S,4R,5S,6R)-5,6-bis(4-prop-2-enoxybut-2-ynoxy)bicyclo[2.2.1]hept-2-ene | 630400-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4R,5S,6R)-5,6-bis(4-prop-2-enoxybut-2-ynoxy)bicyclo[2.2.1]hept-2-ene
• CAS: 630400-77-0
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: MRKMGFXBYXBPBH-FXELSEDVSA-N

物化性质

• 沸点：
  449.7±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙烯 、 (1S,4R,5S,6R)-5,6-bis(4-prop-2-enoxybut-2-ynoxy)bicyclo[2.2.1]hept-2-ene 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以18%的产率得到(4aS,4bR,8aS,9aR)-2,7-Bis-(1-allyloxymethyl-vinyl)-4a,4b,6,8a,9,9a-hexahydro-3H-4,5-dioxa-fluorene
  参考文献：
  名称：

  Ene-yne-ene and ene-yne-yne metathesis of norbornene derivatives

  摘要：

  Norbornene derivatives 4 and 5 containing sidechains bearing an internal alkyne and either a terminal alkene or a terminal alkyne were found to undergo a cascade of metathesis reactions when treated with ruthenium based metathesis catalysts to form highly functionalised pentacyclic products. The reactions illustrate an interesting difference in reactivity between Grubbs' catalyst and the second generation catalyst, with the former being more reactive for the early steps of the cascade. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.035
• 作为产物：
  描述：

  4-(allyloxy)but-2-yn-1-ol 在 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,4R,5S,6R)-5,6-bis(4-prop-2-enoxybut-2-ynoxy)bicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Ene-yne-ene and ene-yne-yne metathesis of norbornene derivatives

  摘要：

  Norbornene derivatives 4 and 5 containing sidechains bearing an internal alkyne and either a terminal alkene or a terminal alkyne were found to undergo a cascade of metathesis reactions when treated with ruthenium based metathesis catalysts to form highly functionalised pentacyclic products. The reactions illustrate an interesting difference in reactivity between Grubbs' catalyst and the second generation catalyst, with the former being more reactive for the early steps of the cascade. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.035

文献信息

• Ene–yne metathesis of polyunsaturated norbornene derivatives
  作者：Donatella Banti、Elisabetta Groaz、Michael North

  DOI：10.1016/j.tet.2004.06.114

  日期：2004.9

  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.