endo-5-methylbicyclo<2.2.2>oct-2-ene | 4517-47-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: endo-5-methylbicyclo<2.2.2>oct-2-ene
• 英文别名: 5-endo-methylbicyclo[2.2.2]oct-2-ene；5-endo-methylbicyclo<2,2,2>oct-2-ene；endo-2-Methylbicyclo-<2,2,2>oct-5-en；5-Methyl-2-bicyclo<2.2.2>octen；endo-5-methylbicyclo[2.2.2]oct-2-ene；(1S,4R,5S)-5-methylbicyclo[2.2.2]oct-2-ene
• CAS: 4517-47-9；14803-42-0；14926-88-6
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: XOGBWGJGWDPLQZ-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  endo-5-methylbicyclo<2.2.2>oct-2-ene 在 platinum(IV) oxide 氢气 作用下， 生成 2-Methyl-bicyclo<2.2.2>octan
  参考文献：
  名称：

  Stothers,J.B.; Tan,C.T., Canadian Journal of Chemistry, 1976, vol. 54, p. 917 - 925

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (1S,2S,4S)-bicyclo[2.2.2]oct-5-ene-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 endo-5-methylbicyclo<2.2.2>oct-2-ene
  参考文献：
  名称：

  Tichy,M. et al., Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 459 - 468

  摘要：

  DOI：

文献信息

• Bobyleva, A. A.; Belikova, N. A.; Dzhigirkhanova, A. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 797 - 804
  作者：Bobyleva, A. A.、Belikova, N. A.、Dzhigirkhanova, A. V.、Plate, A. L.

  DOI：——

  日期：——
• Thermal Reactions of 8-Methylbicyclo[4.2.0]oct-2-enes:  Competitive Diradical-Mediated [1,3] Sigmatropic, Stereomutation, and Fragmentation Processes
  作者：Xavier S. Bogle、Phyllis A. Leber、Lynne A. McCullough、David C. Powers

  DOI：10.1021/jo051505g

  日期：2005.10.1

  At 275 degrees C, 8-exo-methylbicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,31 sigmatropic rearrangement to 5-methylbicyclo[2.2.2]oct-2-enes, of which the orbital symmetry-allowed si product is only marginally favored over the forbidden sr product; that is, si/sr is 2.4. Accompanying the [1,31 shift are significant amounts of epimerization and fragmentation. The 8-endo epimer 1b, which yields no [1,31 product, experiences primarily direct fragmentation and secondarily epimerization. A diradical intermediate can account for all such observations.
• Nitrogen inversion rates in bicyclo[2.2.2]octyl hydrazines and amines by carbon-13 NMR
  作者：S. F. Nelsen、G. R. Weisman

  DOI：10.1021/ja00423a033

  日期：1976.3
• Stothers,J.B.; Tan,C.T., Canadian Journal of Chemistry, 1976, vol. 54, p. 917 - 925
  作者：Stothers,J.B.、Tan,C.T.

  DOI：——

  日期：——
• Tichy,M. et al., Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 459 - 468
  作者：Tichy,M. et al.

  DOI：——

  日期：——