α-(trimethylsiloxy)-1-cyclohexyl phenyl ketone | 56345-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(trimethylsiloxy)-1-cyclohexyl phenyl ketone
• 英文别名: Phenyl-(1-trimethylsilyloxycyclohexyl)methanone
• CAS: 56345-98-3
• 化学式: C₁₆H₂₄O₂Si
• 分子量: 276.451
• InChiKey: WQGMUMNVQHMSLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-(trimethylsiloxy)-1-cyclohexyl phenyl ketone 在 sodium acetate 作用下， 反应 2.0h， 以86%的产率得到1-羟基环己基苯基甲酮
  参考文献：
  名称：

  Trifluoromethanesulfonic (triflic) acid catalyzed transformations of .alpha.-hydroxy carbonyl compounds

  摘要：

  Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantonone. Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione. Reaction of a series of alpha-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively. The reactions and their suggested mechanism are discussed.

  DOI：

  10.1021/jo00007a048
• 作为产物：
  描述：

  diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 、 环己酮 在 lithium diisopropyl amide 作用下， 生成 α-(trimethylsiloxy)-1-cyclohexyl phenyl ketone
  参考文献：
  名称：

  Trifluoromethanesulfonic (triflic) acid catalyzed transformations of .alpha.-hydroxy carbonyl compounds

  摘要：

  Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantonone. Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione. Reaction of a series of alpha-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively. The reactions and their suggested mechanism are discussed.

  DOI：

  10.1021/jo00007a048

文献信息

• HUENIG S.; WEHNER B., CHEM. BER., 1979, 112, NO 6, 2062-2067
  作者：HUENIG S.、 WEHNER B.

  DOI：——

  日期：——
• KOENIGKRAMER R. E.; ZIMMER H., TETRAHEDRON LETT., 1980, 21, NO 11, 1017-1020
  作者：KOENIGKRAMER R. E.、 ZIMMER H.

  DOI：——

  日期：——
• OLAH, GEORGE A.;WU, AN-HSIANG, J. ORG. CHEM., 56,(1991) N, C. 2531-2534
  作者：OLAH, GEORGE A.、WU, AN-HSIANG

  DOI：——

  日期：——
• HUENIG S.; WEHNER G., SYNTHESIS <SYNT-BF>, 1975, NO 6, 391-392
  作者：HUENIG S.、 WEHNER G.

  DOI：——

  日期：——
• Trifluoromethanesulfonic (triflic) acid catalyzed transformations of .alpha.-hydroxy carbonyl compounds
  作者：George A. Olah、An Hsiang Wu

  DOI：10.1021/jo00007a048

  日期：1991.3

  Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantonone. Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione. Reaction of a series of alpha-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively. The reactions and their suggested mechanism are discussed.