Bicyclo[3.3.2]decan-9-one | 28054-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bicyclo[3.3.2]decan-9-one
• CAS: 28054-91-3
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: QAVLIVNTLHVEGD-UHFFFAOYSA-N

物化性质

• 沸点：
  237.8±8.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  Bicyclo[3.3.2]decan-9-one 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以78%的产率得到bicyclo[3.3.2]decan-9-one oxime
  参考文献：
  名称：

  通过重排步骤方便地制备含杂原子的双环[3.3.3]十一烷衍生物

  摘要：

  摘要 描述了一种通过双环[3,3,2]癸烷-9-one 的贝克曼重排制备双环[3,3,3]十一烷衍生物的简便方法。

  DOI：

  10.1080/00397919808007023
• 作为产物：
  描述：

  双环(3.3.1)壬基-9-酮 、 N-甲基-N-亚硝基对甲苯磺酰胺 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 Bicyclo[3.3.2]decan-9-one
  参考文献：
  名称：

  Synthesis of bridgehead derivatives by chromic acid oxidation

  摘要：

  DOI：

  10.1021/jo00808a008

文献信息

• An Improved Synthesis of Bicyclo[3.3.3]undecane
  作者：Gregory S. Wayne、Gary J. Snyder

  DOI：10.1080/00397919508015479

  日期：1995.10

  Abstract A shorter and significantly higher-yield procedure for the preparation of bicyclo[3.3.3]undecane (manxane) is reported.

  摘要 报道了一种制备双环 [3.3.3] 十一烷 (甘露烷) 的更短且产率显着更高的程序。
• Doyle,M.; Parker,W., Journal of the Chemical Society. Perkin transactions I, 1977, p. 858 - 865
  作者：Doyle,M.、Parker,W.

  DOI：——

  日期：——
• Doyle,M. et al., Journal of the Chemical Society. Perkin transactions I, 1977, p. 364 - 372
  作者：Doyle,M. et al.

  DOI：——

  日期：——
• 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
• METALLKOMPLEXE
  申请人：Merck Patent GmbH

  公开号：EP3094638B1

  公开（公告）日：2017-11-08