1,2,5,5-Tetramethylcyclopenta-1,3-diene | 4249-12-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,2,5,5-Tetramethylcyclopenta-1,3-diene
• 英文别名: 1,2,5,5-tetramethyl-1,3-cyclopentadiene；1,2,5,5-Tetramethyl-cyclopentadien
• CAS: 4249-12-1
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: FZQSOBIGZJECPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,2,5,5-tetramethylcyclopent-3-en-1-yl p-toluenesulfonate 在 2,6-二甲基吡啶 作用下， 以 乙醇 、 水 为溶剂， 生成 1,2,5,5-Tetramethylcyclopenta-1,3-diene
  参考文献：
  名称：

  Inductive effects in neighboring-group participation. Destabilization of carbocations by CC double bonds in solvolyses of 2,2,5,5-tetramethylcyclopent-3-en-1-yl tosylates

  摘要：

  DOI：

  10.1021/jo00250a015

文献信息

• Substitution in the cyclopentadienide anion series
  作者：S. McLean、P. Haynes

  DOI：10.1016/s0040-4020(01)93888-8

  日期：1965.1
• Photosensitized electron transfer from azoalkanes: generation, fragmentation, and rearrangement of radical cations structurally related to dicyclopentadiene
  作者：Waldemar Adam、Juergen Sendelbach

  DOI：10.1021/jo00072a008

  日期：1993.9

  The azoalkanes 1a-c extrude nitrogen upon photosensitized electron transfer (PET) to yield 1,3-radical cation intermediates 2.+, which undergo interesting transformations. Electron back transfer (BET) affords the unrearranged housanes 2, but significant rearrangement to dicyclopentadiene derivatives 3 occurs prior to BET. In some cases, fragmentation to cyclopentadienes 4 is observed, a cycloreversion that occurs at the 1,3-radial cation stage rather than through the corresponding 1,3-biradical intermediates. The diphenyl-substituted azoalkane la affords high yields of the symmetric cyclopentadiene 4a, while the alkyl-substituted lb produces only small amounts of a rearranged cyclopentadiene 4'b. The housanes 2a,b are also oxidized by PET, but are more reluctant to rearrange. Strong electron acceptors such as triphenylpyrylium tetrafluoroborate (TPT) or cosensitization with biphenyl (Ph2) must be utilized to induce rearrangement to 3a,b and fragmentation to 4 and 4'.
• BENTLEY, T. WILLIAM;IRRGANG, BERNHARD;MAYR, HERBERT;SCHLEYER, PAUL VON RE+, J. ORG. CHEM., 53,(1988) N 15, C. 3492-3498
  作者：BENTLEY, T. WILLIAM、IRRGANG, BERNHARD、MAYR, HERBERT、SCHLEYER, PAUL VON RE+

  DOI：——

  日期：——
• Inductive effects in neighboring-group participation. Destabilization of carbocations by CC double bonds in solvolyses of 2,2,5,5-tetramethylcyclopent-3-en-1-yl tosylates
  作者：T. William Bentley、Bernhard Irrgang、Herbert Mayr、Paul v. R. Schleyer

  DOI：10.1021/jo00250a015

  日期：1988.7