3-(Dimethyl-phenyl-silanyl)-3,5,5-trimethyl-cyclohexanone | 67263-02-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-(Dimethyl-phenyl-silanyl)-3,5,5-trimethyl-cyclohexanone
• 英文别名: 3-[Dimethyl(phenyl)silyl]-3,5,5-trimethylcyclohexan-1-one
• CAS: 67263-02-9
• 化学式: C₁₇H₂₆OSi
• 分子量: 274.478
• InChiKey: IVWJHVRSFJNJAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  异佛尔酮 、 dimethyl(phenyl)silyllithium 在 copper(l) iodide 作用下， 以68%的产率得到3-(Dimethyl-phenyl-silanyl)-3,5,5-trimethyl-cyclohexanone
  参考文献：
  名称：

  甲硅烷基在烯酮上的共轭加成和用溴化铜（II）的去除：αβ-不饱和酮的αβ-不饱和保护基

  摘要：

  与铜（I）盐混合的甲硅烷基锂试剂与烯酮（包括酯和醛）反应，以高收率得到β-甲硅烷基羰基化合物。β-甲硅烷基酮可用于合成而没有甲硅烷基基团的风险，并且烯酮基团可通过用溴化铜（II）进行溴化-脱甲硅烷基溴化来恢复。香芹酮和二氢茉莉酮的合成说明了该原理。

  DOI：

  10.1039/p19810002520

文献信息

• Copper-Catalyzed Conjugate Addition of a Bis(triorganosilyl) Zinc and a Methyl(triorganosilyl) Magnesium
  作者：Martin Oestreich、Barbara Weiner

  DOI：10.1055/s-2004-831331

  日期：——

  A practical copper-catalyzed conjugate silylation of α,β-unsaturated carbonyl compounds 4 utilizing bis(triorganosilyl) zinc reagent 3 is described. Moreover, mixed methyl(triorganosilyl) magnesium 7 also transfers its silyl ligand to simple enones 4 under copper catalysis.

  描述了使用双（三有机甲硅烷基）锌试剂 3 对 α,β-不饱和羰基化合物 4 进行实用的铜催化共轭甲硅烷基化反应。此外，混合甲基（三有机甲硅烷基）镁 7 还在铜催化下将其甲硅烷基配体转移到简单的烯酮 4 上。
• The conjugate addition of a silyl group to enones and its removal with copper(<scp>II</scp>) bromide: a protecting group for the αβ-unsaturation of αβ-unsaturated ketones
  作者：David J. Ager、Ian Fleming、Shailesh K. Patel

  DOI：10.1039/p19810002520

  日期：——

  copper(I) salts react with enones, including esters and aldehydes, to give β-silyl carbonyl compounds in good yield. The β-silylketones can be used in synthesis without risk to the silyl group and the enone group can be restored by bromination-desilylbromination with copper(II) bromide. The principle is illustrated with syntheses of carvone and dihydrojasmone.

  与铜（I）盐混合的甲硅烷基锂试剂与烯酮（包括酯和醛）反应，以高收率得到β-甲硅烷基羰基化合物。β-甲硅烷基酮可用于合成而没有甲硅烷基基团的风险，并且烯酮基团可通过用溴化铜（II）进行溴化-脱甲硅烷基溴化来恢复。香芹酮和二氢茉莉酮的合成说明了该原理。
• Conjugate addition of dimethylphenylsilyllithium to α,β-unsaturated carbonyl compounds mediated by sub-stoichiometric quantities of dimethylzinc
  作者：Bonnie L. MacLean、Kimberlea A. Hennigar、Kevin W. Kells、Robert D. Singer

  DOI：10.1016/s0040-4039(97)01776-0

  日期：1997.10

  Dimethylphenylsilyllithium undergoes conjugate addition to a variety of alpha,beta-unsaturated enones in the presence of sub-stoichiometric amounts of dimethylzinc. Down to 10 mol % of Me2Zn facilitates these reactions to afford good to excellent yields of beta-silylated products. This catalytic behavior is displayed when the Me2Zn used is generated in situ from the addition of methyllithium to zinc (II) iodide or when used directly from a commercial source. This methodology in which sub-stoichiometric quantities of the reactive organometallic reagent are present at a given time may provide a route for catalytic enantioselective conjugate addition of trialkylsilyl moieties to enones. (C) 1997 Elsevier Science Ltd.
• Crump, Roger A. N. C.; Fleming, Ian; Urch, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 701 - 706
  作者：Crump, Roger A. N. C.、Fleming, Ian、Urch, Christopher J.

  DOI：——

  日期：——
• AGER, D. J.;FLEMING, I.;PATEL, SH. K., J. CHEM.SOC. PERKIN TRANS., 1981, N 9, 2520-2526
  作者：AGER, D. J.、FLEMING, I.、PATEL, SH. K.

  DOI：——

  日期：——