Basketen | 5603-34-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: Basketen
• 英文别名: Pentacyclo(4.4.0.02,5.03,8.04,7)dec-9-ene；pentacyclo[4.4.0.02,5.03,8.04,7]dec-9-ene
• CAS: 5603-34-9
• 化学式: C₁₀H₁₀
• 分子量: 130.189
• InChiKey: LXQOIQYQFRKBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  Basketen 在 palladium on activated charcoal 氢气 作用下， 以 正己烷 为溶剂， 生成 (+/-)-<2.0>triblattane
  参考文献：
  名称：

  Sasaki,N.A. et al., Chemische Berichte, 1973, vol. 106, p. 2992 - 3000

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-pentacyclo<6.2.0.0^2,7.0^3,9.0^6.10>decane-4,5-dicarboxylic acid 在 吡啶 、 lead(IV) acetate 作用下， 反应 3.0h， 以47.4%的产率得到Basketen
  参考文献：
  名称：

  Torsional effects on the conformations of two diastereomeric tetracyclic bis(hydrazines)

  摘要：

  The symmetrical tetraazatetracyclotetradecadiene (1) is bis(tert-butylated) (tert-butyl alcohol/H+) and bis(methylated) (methyllithium) to a 1:1 mixture of diastereomeric bis(tert-butylmethylhydrazines) with like alkyl groups anti (9a) and syn (9s). 9a has the expected C2 symmetry on the NMR time scale (both tert-butyl groups are directed away from the central CC bond, conformation Oi,Oi in Scheme II). 9s does not have the expected C(s) symmetry, but has one tert-butyl group directed away from the central CC bond and one directed toward it (conformations Oi,oI and Io,iO in Scheme II). Both diastereomers also crystallize in these conformations. AM1 calculations carried out using VAMP both predict this result and show it to be caused by tetracyclic ring torsion (experimentally approximately 12.7-degrees about the central CC bond for crystalline 9a, approximately 13.2-degrees for 9s).

  DOI：

  10.1021/ja00021a009

文献信息

• Kaufmann, Dieter; Fick, Hans-Heinrich; Schallner, Otto, Chemische Berichte, 1983, vol. 116, # 2, p. 587 - 609
  作者：Kaufmann, Dieter、Fick, Hans-Heinrich、Schallner, Otto、Spielmann, Werner、Meyer, Lueder-Ulrich、et al.

  DOI：——

  日期：——
• Molecular design by cycloaddition reactions. XXIII. Synthesis of some highly strained bridged polycyclic hydrocarbons
  作者：Tadashi Sasaki、Ken Kanematsu、Naoya Okamura

  DOI：10.1021/jo00911a003

  日期：1975.11
• Synthesis and rearrangement of strained cage molecules
  作者：William G. Dauben、Charles H. Schallhorn、Dale L. Whalen

  DOI：10.1021/ja00735a021

  日期：1971.3
• 10.1002/1099-0690(200207)2002:14<2280::aid-ejoc2280<3.0.co;2-r
  作者：Verevkin, Sergei P.、Kuemmerlin, Martin、Hickl, Ernst、Beckhaus, Hans-Dieter、Ruechardt, Christoph、Kozhushkov, Sergei I.、Haag, Rainer、Boese, Roland、Benet-Bucholz, Jordi、Nordhoff, Karsten、De Meijere, Armin

  DOI：10.1002/1099-0690(200207)2002:14<2280::aid-ejoc2280<3.0.co;2-r

  日期：——
• Electrocyclic additions to pentacyclo[4.4.02,5.03,8.04,7]deca-9-ene
  作者：E. LeGoff、S. Oka

  DOI：10.1021/ja01048a054

  日期：1969.9