3-Methyl-bicyclo<2.2.2>octan-2-on | 26051-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methyl-bicyclo<2.2.2>octan-2-on
• 英文别名: Bicyclo[2.2.2]octanone, 3-methyl-；3-methylbicyclo[2.2.2]octan-2-one
• CAS: 26051-25-2
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: RMZQBMVYJTYCBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  3-Methyl-bicyclo<2.2.2>octan-2-on 、 碘甲烷 在 (三苯基甲基)-锂 作用下， 生成 3,3-dimethylbicyclo<2.2.2>octan-2-one
  参考文献：
  名称：

  Magnetic circular dichroism studies—XLVI

  摘要：

  DOI：

  10.1016/0040-4020(77)80044-6
• 作为产物：
  描述：

  双环[2.2.2]辛烷-3-酮 、 lithium diisopropyl amide 、 碘甲烷 以39%的产率得到
  参考文献：
  名称：

  SANTIAGO, ANA N.;TAKEUCHI, KENICHI;OHGA, YASUSHI;NISHIDA, MITSUO;ROSSI, R+, J. ORG. CHEM., 56,(1991) N, C. 1581-1584

  摘要：

  DOI：

文献信息

• Magnetic circular dichroism studies—XLVI
  作者：Kent Morrill、Robert E. Linder、Edith M. Bruckmann、Günter Barth、Edward Bunnenberg、Carl Djerassi、Lloyd Seamans、Albert Moscowitz

  DOI：10.1016/0040-4020(77)80044-6

  日期：——
• SANTIAGO, ANA N.;TAKEUCHI, KENICHI;OHGA, YASUSHI;NISHIDA, MITSUO;ROSSI, R+, J. ORG. CHEM., 56,(1991) N, C. 1581-1584
  作者：SANTIAGO, ANA N.、TAKEUCHI, KENICHI、OHGA, YASUSHI、NISHIDA, MITSUO、ROSSI, R+

  DOI：——

  日期：——
• HOYANO Y.; PATEL V.; STOTHERS J. B., CAN. J. CHEM., 1980, 58, NO 23, 2730-2735,
  作者：HOYANO Y.、 PATEL V.、 STOTHERS J. B.

  DOI：——

  日期：——
• The reactivity of 1-chloro-3,3-dimethylbicyclo[2.2.2]octan-2-one in the radical mechanism of nucleophilic substitution
  作者：Ana N. Santiago、Ken'ichi Takeuchi、Yasushi Ohga、Mitsuo Nishida、Roberto A. Rossi

  DOI：10.1021/jo00004a044

  日期：1991.2

  1-Chloro-3,3-dimethylbicyclo[2.2.2]octan-2-one (5) does not react with diphenyl phosphide ions (4) in liquid ammonia in the dark in 240 min, but under irradiation (30 min) it good yields of the substitution product (10) isolated as the oxide 12 (69% yield) and 3% yield of the reduction product 3,3-dimethylbicyclo[2.2.2]octan-2-one (11). This photostimulated reaction is inhibited by p-dinitrobenzene and 2,2,6,6-tetramethyl-1-piperidinyloxy. In competition experiments 5 is more reactive (greater-than-or-equal-to 700) than 1-chloroadamantane (3a) and only slightly less reactive than 1-bromoadamantane (3b) (0.40) toward diphenyl phosphide ions. On the other hand, 1-chloro-3,3-dimethylbicyclo[2.2.2]octane (6) was completely unreactive toward 4 under irradiation. We suggest that the bridgehead chloride 5 reacts by the S(RN)1 mechanism of nucleophilic substitution and that the 2-oxo substituent increases the reactivity of the chloride due to the LUMO of the carbonyl group.