1,2,2a,10b-tetramethyl-2a,10b-dihydrocyclobuta[l]phenanthrene | 666754-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1,2,2a,10b-tetramethyl-2a,10b-dihydrocyclobuta[l]phenanthrene
• CAS: 666754-22-9
• 化学式: C₂₀H₂₀
• 分子量: 260.379
• InChiKey: GZYPIFWDJBMLCU-BGYRXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,2,2a,10b-tetramethyl-2a,10b-dihydrocyclobuta[l]phenanthrene 在 三氟甲磺酸 作用下， 以 氘代氯仿 为溶剂， 生成 trans-4,5,6,6-tetramethyl-4,5,6-trihydrocyclopenta[j,k]phenanthren-5-yl cation
  参考文献：
  名称：

  Carbocationic Cyclizations: IX. Rearrangement of Long-Lived 4-(2-Biphenylyl)-1,2,3,4-tetramethylcyclobutenyl Cation into trans- and cis-4,5,6,6-Tetramethyl-4,5,6-trihydrocyclopenta[j,k]phenanthren-5-yl Cations

  摘要：

  According to the H-1 and C-13 NMR data, long-lived 4-(2-biphenylyl)-1,2,3,4-tetramethylcyclobutenyl cation generated by protonation of 3-(2-biphenylyl)-1,2,3-trimethyl-4-methylenecyclobutene in superacids undergoes cyclization which launches further rearrangements finally leading to formation of a mixture of trans- and cis-4,5,6,6-tetramethyl-4,5,6-trihydrocyclopenta[j,k]phenanthren-5-yl cations.

  DOI：

  10.1023/b:rujo.0000010218.88703.55
• 作为产物：
  描述：

  3-(2-biphenylyl)-1,2,3-trimethyl-4-methylenecyclobuten 以61%的产率得到1,2,2a,10b-tetramethyl-2a,10b-dihydrocyclobuta[l]phenanthrene
  参考文献：
  名称：

  Carbocationic Cyclizations: IX. Rearrangement of Long-Lived 4-(2-Biphenylyl)-1,2,3,4-tetramethylcyclobutenyl Cation into trans- and cis-4,5,6,6-Tetramethyl-4,5,6-trihydrocyclopenta[j,k]phenanthren-5-yl Cations

  摘要：

  According to the H-1 and C-13 NMR data, long-lived 4-(2-biphenylyl)-1,2,3,4-tetramethylcyclobutenyl cation generated by protonation of 3-(2-biphenylyl)-1,2,3-trimethyl-4-methylenecyclobutene in superacids undergoes cyclization which launches further rearrangements finally leading to formation of a mixture of trans- and cis-4,5,6,6-tetramethyl-4,5,6-trihydrocyclopenta[j,k]phenanthren-5-yl cations.

  DOI：

  10.1023/b:rujo.0000010218.88703.55

文献信息

• Degenerate Rearrangement of Long-Lived 9,10-Dimethyl-9-(cis-1-methyl-1-propenyl)phenanthrenium Ion: 1,2-Shift of the Dimethylvinyl Group
  作者：V. A. Bushmelev、A. M. Genaev、V. G. Shubin

  DOI：10.1023/b:rujo.0000045186.11978.a5

  日期：2004.7

  Dynamic NMR study showed that 9,10-dimethyl-9-(cis-1-methyl-1-propenyl)phenanthrenium ion generated by reaction of 1,2,2a,10b-tetramethyl-2a,10b-dihydrocyclobuta[l]phenanthrene with HSO3F below -100degreesC undergoes very fast (DeltaG(not equal) = 22 kJ/mol at -120degreesC) degenerate 1,2-shift of the dimethylvinyl group.
• Degenerate rearrangement of 9,10-dimethyl-9-(cis-1-methylprop-1-enyl)phenanthrenium cation. First example for the 1,2-vinyl shift in the persistent carbocation
  作者：V. A. Bushmelev、A. M. Genaev、V. G. Shubin

  DOI：10.1007/s11172-005-0211-x

  日期：2004.12