(1R,2S,4R,5S)-3,3-Dimethyl-2,4-diphenyl-tricyclo[3.2.0.0^2,4]hept-6-ene | 34783-15-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: (1R,2S,4R,5S)-3,3-Dimethyl-2,4-diphenyl-tricyclo[3.2.0.0^2,4]hept-6-ene
• 英文别名: (1S,2R,4S,5R)-3,3-dimethyl-2,4-diphenyltricyclo[3.2.0.02,4]hept-6-ene
• CAS: 34783-15-8
• 化学式: C₂₁H₂₀
• 分子量: 272.39
• InChiKey: CHKJVZRGMOCLPQ-GHSBBIOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (1R,2S,4R,5S)-3,3-Dimethyl-2,4-diphenyl-tricyclo[3.2.0.0^2,4]hept-6-ene 在 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (1R,2S,4R,5S)-3,3-Dimethyl-2,4-diphenyl-tricyclo[3.2.0.0^2,4]heptane
  参考文献：
  名称：

  Thermally promoted cleavage reactions of anti-tricyclo[3.2.0.02,4] heptanes. Influence of 2,4 substitution on competitive bond scission processes

  摘要：

  DOI：

  10.1021/jo00918a009
• 作为产物：
  描述：

  endo-7,8-Diaza-9,9-dimethyl-1,6-diphenyl-tricyclo<4.2.1.0^2.5>-nona-3,7-dien 以 乙醚 为溶剂， 生成 (1R,2S,4R,5S)-3,3-Dimethyl-2,4-diphenyl-tricyclo[3.2.0.0^2,4]hept-6-ene
  参考文献：
  名称：

  Synthesis and thermal rearrangement of tricyclo[3.2.02,4]hept-6-enes. Analysis of structural requirements for effective intramolecular trapping of a 1,3-diradical by a remote cyclobutene ring

  摘要：

  DOI：

  10.1021/ja00749a029

文献信息

• Dissolving metal reduction of anti-tricyclo[3.2.0.02,4]heptanes and anti-tricyclo[3.3.0.02,4]octanes. Intramolecular epoxide cleavage as a route to highly strained tricyclic alcohols
  作者：Leo A. Paquette、Kenneth H. Fuhr、Spencer Porter、Jon Clardy

  DOI：10.1021/jo00918a010

  日期：1974.2
• Generation of Bicyclo[3.2.0]hept-6-ene-2,4-diyl Radical Cations by Chemical Electron Transfer (CET) with Trisarylaminium Salts and Intramolecular Cyclobutene Trapping as an Alternative Entry to the Quadricyclane-Norbornadiene Valence Isomers
  作者：Waldemar Adam、Thomas Heidenfelder、Coskun Sahin

  DOI：10.1021/ja00143a012

  日期：1995.9

  For the first time, chemical electron transfer (CET) studies have been conducted for the tricyclo[3.2.0.0(2,4)]-hept-6-enes 2 and the quadricyclanes 3 in solution. The 2,4-dimethyl-sustituted bicyclo[3.2.0]hept-6-ene-2,4-diyl radical cation 2a(.+), generated by trisarylaminium salt oxidation of 2a, is intramolecularly trapped by the juxtaposed cyclobutenyl double bond to afford the quadricyclane radical cation 3a(.+) in addition to the expected 1,2-methyl migration to the bicyclo[3.2.0]hepta-2,6-diene radical cation 6a(.+). Radical cation 3a(.+) leads to the norbornadiene 4a by valence isomerization and the bicyclo[3.2.0]hepta-2,6-diene 5a by skeletal rearrangement. For comparison, oxidation of quadricyclane 3a yields exclusively norbornadiene 4a. Whereas the 2,4-diphenyl-substituted bicycle[3.2.0]hept-6-ene-2,4-diyl radical cation 2b(.+) derived from 2b is intramolecularly trapped by the juxtaposed cyclobutenyl double bond to afford norbornadiene 4b and bicyclo[3.2.0]hepta-2,6-diene 5b through the quadricyclane radical cation 3b(.+), the quadricyclane 3b yields on oxidation also 5b besides 4b. These experimental facts are rationalized in terms of distinct radical cation structures, namely the pi complex (oxidation of the lateral cyclopropane bond) and trimethylene (oxidation of the internal cyclopropane bond). Their preferences are dictated by the substrate structure, i.e., tricycloheptene 2 versus quadricyclane 3 as well as by the substitution type (phenyl versus methyl) and is corroborated by AM1 calculations.
• Synthesis and thermal rearrangement of tricyclo[3.2.02,4]hept-6-enes. Analysis of structural requirements for effective intramolecular trapping of a 1,3-diradical by a remote cyclobutene ring
  作者：Leo A. Paquette、Louis M. Leichter

  DOI：10.1021/ja00749a029

  日期：1971.10
• Thermally promoted cleavage reactions of anti-tricyclo[3.2.0.02,4] heptanes. Influence of 2,4 substitution on competitive bond scission processes
  作者：Leo A. Paquette、Louis M. Leichter

  DOI：10.1021/jo00918a009

  日期：1974.2