三环[5.1.0.03,5]辛烷 | 285-50-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 中文名称: 三环[5.1.0.03,5]辛烷
• 英文名称: Tricyclo<5.1.0.0^3,5>octane
• 英文别名: Tricyclo<5.1.0.0^3.5>octane；Tricyclo[5.1.0.03,5]octane
• CAS: 285-50-7
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: YZFVTGCKLQCIFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  三环[5.1.0.03,5]辛烷 在 3,5-二甲基吡唑 、 chromium(VI) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (1α,2α/β,3α,5α,7α)-2-Methyltricyclo<5.1.0.0^3,5>octan-2-ol
  参考文献：
  名称：

  13C-1H Coupling Constants in Carbocations. 8. Application of the .DELTA.J Equation to Tertiary Dicyclopropylcarbinyl Cations: the Methyldicyclopropylcarbinyl, (1.alpha.,3.beta.,5.beta.,7.alpha.)-2-Methyltricyclo[5.1.0.03,5]octan-2-yl, (1.alpha.,3.alpha.,5.alpha.,7.alpha.)-2-Methyltricyclo[5.1.0.03,5]octan-2-yl, and 3-Methyltetracyclo[3.3.1.02,8.04,6]nonan-3-yl (Triasteryl) Cations

  摘要：

  One-bond C-13-H-1 coupling constants have been determined for the title cations (10, 15, 20, and 25) in superacids and the values for the carbons adjacent (alpha) to the cationic centers compared with those of the appropriate model ketones to obtain the Delta J values. These values were found to be in the range 10-15 Hz, approximately one half that expected for a single cyclopropylcarbinyl cation. This has been interpreted in terms of delocalization of charge into the second cyclopropyl group in those cations which can adopt double bisected conformers, 10, 20, 25, and in terms of averaging of the coupling constants as a result of two different dihedral angles in cation 15. New methods for the synthesis of precursors to the 2-methyltricyclo[5.1.0.0(3,5)]octan-2-yl cations, 15 and 20, have been developed.

  DOI：

  10.1021/jo00111a025
• 作为产物：
  描述：

  4,4,8,8-tetrachlorotricyclo<5.1.0^1,7.0^3,5>octane 在 氨 、 氢化钾 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到三环[5.1.0.03,5]辛烷
  参考文献：
  名称：

  Electron-transfer reduction of bis(gem-dihalocyclopropyl) compounds. Evidence against the 1,4-elimination-type remote ionization of the cyclopropylidene radical anion. Unusual product distribution as a result of reactions in the region of reagent mixing

  摘要：

  DOI：

  10.1021/jo00152a046

文献信息

• 13C-1H Coupling Constants in Carbocations. 8. Application of the .DELTA.J Equation to Tertiary Dicyclopropylcarbinyl Cations: the Methyldicyclopropylcarbinyl, (1.alpha.,3.beta.,5.beta.,7.alpha.)-2-Methyltricyclo[5.1.0.03,5]octan-2-yl, (1.alpha.,3.alpha.,5.alpha.,7.alpha.)-2-Methyltricyclo[5.1.0.03,5]octan-2-yl, and 3-Methyltetracyclo[3.3.1.02,8.04,6]nonan-3-yl (Triasteryl) Cations
  作者：David P. Kelly、Martin G. Banwell、John H. Ryan、James R. Phyland、Jason R. Quick

  DOI：10.1021/jo00111a025

  日期：1995.3

  One-bond C-13-H-1 coupling constants have been determined for the title cations (10, 15, 20, and 25) in superacids and the values for the carbons adjacent (alpha) to the cationic centers compared with those of the appropriate model ketones to obtain the Delta J values. These values were found to be in the range 10-15 Hz, approximately one half that expected for a single cyclopropylcarbinyl cation. This has been interpreted in terms of delocalization of charge into the second cyclopropyl group in those cations which can adopt double bisected conformers, 10, 20, 25, and in terms of averaging of the coupling constants as a result of two different dihedral angles in cation 15. New methods for the synthesis of precursors to the 2-methyltricyclo[5.1.0.0(3,5)]octan-2-yl cations, 15 and 20, have been developed.
• Electron-transfer reduction of bis(gem-dihalocyclopropyl) compounds. Evidence against the 1,4-elimination-type remote ionization of the cyclopropylidene radical anion. Unusual product distribution as a result of reactions in the region of reagent mixing
  作者：Michael J. Tremelling、Sarjit Kaur

  DOI：10.1021/jo00152a046

  日期：1983.2