(1S,4R,5S,6R)-5,6-Bis-(4-but-2-ynyloxy-but-2-ynyloxy)-bicyclo[2.2.1]hept-2-ene | 769135-99-1

• 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-but-2-ynyloxy-but-2-ynyloxy)-bicyclo[2.2.1]hept-2-ene
• CAS: 769135-99-1
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: PTUQCMBZSZFTNE-MESAYYPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  乙烯 、 (1S,4R,5S,6R)-5,6-Bis-(4-but-2-ynyloxy-but-2-ynyloxy)-bicyclo[2.2.1]hept-2-ene 在 tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以11%的产率得到(4aS,4bR,8aS,9aR)-2,7-Bis-[1-(3-methyl-2-methylene-but-3-enyloxymethyl)-vinyl]-4a,4b,6,8a,9,9a-hexahydro-3H-4,5-dioxa-fluorene
  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：

  5-oxanona-2,7-diyn-1-ol 在 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 (1S,4R,5S,6R)-5,6-Bis-(4-but-2-ynyloxy-but-2-ynyloxy)-bicyclo[2.2.1]hept-2-ene
  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