三环[3.2.1.13,6]壬烷-7-酮 | 17931-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 三环[3.2.1.13,6]壬烷-7-酮
• 英文名称: tricyclo<3.3.1.0^3,7>nonan-2-one
• 英文别名: Neoadamantan-2-one；noradamantan-2-one；2-Noradamantanone；Noradamantanon-(2)；Noradamantan-2-on；2-Noradamantanon；Tricyclo(3.2.1.13,6)nonan-7-one；tricyclo[3.3.1.03,7]nonan-2-one
• CAS: 17931-67-8
• 化学式: C₉H₁₂O
• mdl: MFCD24393542
• 分子量: 136.194
• InChiKey: QUXWGFTVVNVNFO-UHFFFAOYSA-N

物化性质

• 熔点：
  211-213 °C
• 沸点：
  230.9±8.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  三环[3.2.1.13,6]壬烷-7-酮 生成 (NE)-N-(2-tricyclo[3.3.1.03,7]nonanylidene)hydroxylamine
  参考文献：
  名称：

  GEVORKYAN, G. G.;ORDUBADI, M. D.;BELIKOVA, N. A.;BOREKO, E. I.;VLADYKO, G+, XIM.-FARMATS. ZH., 23,(1989) N, S. 963-966

  摘要：

  DOI：
• 作为产物：
  描述：

  5-Diazo-4-protoadamantanone 在 氧气 作用下， 生成 三环[3.2.1.13,6]壬烷-7-酮
  参考文献：
  名称：

  A New, One-Pot Preparation of Alicyclic Ketones via WoIff Rearrangement

  摘要：

  δ-重氮环烷酮的光氧化反应通过沃尔夫重排作用导致环收缩，从而以中等至良好的收率得到环烷酮。

  DOI：

  10.1055/s-1989-27319

文献信息

• The manifestation of non-bonded attraction in the physical properties of cis and trans olefins
  作者：N.D. Epiotis、S. Shaik、J.R. Larson、F. Bernardi

  DOI：10.1016/0040-4020(77)80149-x

  日期：1977.1

  Non-bonded attraction is suggested to account for a host of differences in the physical properties of cis and trans olefins of the type XHCCHX. The main predictions are: (i) The cis isomer is more stable than the trans isomer; (ii) The CC bond is longer and the C-X bonds are shorter for the cis isomer; (iii) The π MO's orbital energies of the two isomers differ such that the trans isomer is a better

  建议使用非键合吸附来解决XHCCHX类型的顺式和反式烯烃的物理性质差异。主要预测为：（i）顺式异构体比反式异构体稳定；（ii）顺式异构体的CC键较长而CX键较短；（iii）两种异构体的πMO轨道能不同，使得反式异构体比顺式异构体更好地是电子给体和电子受体。提出了支持该模型的STO-3G和4-31G级别的从头算计算。的光电子能谱顺和对反式二氟，二氯和二溴乙烯进行了讨论，发现与我们的定性模型相符。
• On the reaction of (dibromomethyl)lithium with bicyclic and tricyclic ketones
  作者：David S. Teager、Harry D. Ward、Roger K. Murray

  DOI：10.1021/jo00072a037

  日期：1993.9

  Many literature examples show that the reaction of a simple cyclic ketone with (dibromomethyl)-lithium at -78-degrees-C followed by low-temperature hydrolysis of the resulting lithium alkoxide 33, gives the corresponding dibromomethyl alcohol. We have found that the reaction of a bicyclic or tricyclic ketone with (dibromomethyl)lithium under comparable conditions provides a dibromomethyl alcohol and/or an alpha-bromo aldehyde. The latter product appears to result from an intramolecular displacement reaction in 33 to give a bromo epoxide, which then rearranges stereospecifically to the alpha-bromo aldehyde. The product ratios obtained in all of these reactions seem to be determined by the steric interactions in 33 between the alkoxide and dibromomethyl groups and the hydrogens that are syn to them at the carbons which are beta to the original carbonyl carbon. As these steric interactions increase, the proportion of alpha-bromo aldehyde in the product mixture increases. If 33 obtained from any cyclic ketone is warmed to 10-degrees-C before it is hydrolyzed, then the only product isolated is the alpha-bromo aldehyde
• Bishop, Roger; Lee, Gum-Hee, Australian Journal of Chemistry, 1987, vol. 40, # 2, p. 249 - 255
  作者：Bishop, Roger、Lee, Gum-Hee

  DOI：——

  日期：——
• Gevorkyan, G. G.; Ordubadi, M. D.; Pekhk, T. I., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 7.1, p. 1280 - 1286
  作者：Gevorkyan, G. G.、Ordubadi, M. D.、Pekhk, T. I.、Belikova, N. A.

  DOI：——

  日期：——
• Synthesis and chemistry of 2,8-disubstituted noradamantanes
  作者：Zdenko Majerski、Zdenko Hamersak

  DOI：10.1021/jo00181a007

  日期：1984.4