2-(2,2-dimethylpropyl)cyclohexanone | 72653-53-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,2-dimethylpropyl)cyclohexanone
• 英文别名: 2-(2,2-Dimethylpropyl)cyclohexan-1-one
• CAS: 72653-53-3
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: HDXQEFVDEMNCFH-UHFFFAOYSA-N

物化性质

• 沸点：
  217.8±8.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  1-环己烯氧基三甲基硅烷 在 W-2 Raney nickel zinc dibromide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 2-(2,2-dimethylpropyl)cyclohexanone
  参考文献：
  名称：

  羰基化合物的α-烷基化和α-烷基化通过邻甲硅烷基化的烯醇式苯硫基烷基化

  摘要：

  对于羰基旁边的许多反应，使用O-甲硅烷基化的烯醇盐化学方法比第I组金属烯醇盐的相应反应提供了更高的产率和选择性。在羰基化合物，路易斯酸（的TiCl 4的α-烷基化的情况下，4或ZnBr 2）促进了phenylthioalkylation ö -silylated烯醇化物3由α-chlorosulphides 4（R 3 = H，Me中，镨Ñ，镨我，卜吨，和Me 3 Si），然后通过阮内镍从5→6进行还原性硫去除，被认为是此合成上重要的CC键形成步骤的可靠方法。一种替代硫消除途径经由5→7的亚砜可使羰基化合物进行区域和立体控制的α-亚烷基化。苯硫基烷基化反应适用于酮，醛，酯和内酯。

  DOI：

  10.1016/s0040-4020(01)86667-9

文献信息

• Deprotonation of chelating enamines. Direct formation of .beta.-lithio enamines
  作者：Gilbert. Stork、Christopher S. Shiner、Chi Wen. Cheng、Robin L. Polt

  DOI：10.1021/ja00262a025

  日期：1986.1

  Deprotonation de la N-[cyclohexene-1 yl] N,N',N'-trimethyl ethylenediamine et d'une N-vinyl N,N',N'-trimethyl ethylenediamine

  N-[环己烯-1基] N,N',N'-三甲基乙二胺和N-乙烯基N,N',N'-三甲基乙二胺的去质子化
• Cyclizations in the homolytic reactions of unsaturated nitriles withtert-butylmercury halides in the presence of proton donors
  作者：Glen A. Russell、Ping Chen

  DOI：10.1002/(sici)1099-1395(1998100)11:10<715::aid-poc30>3.0.co;2-e

  日期：1998.10

  Cyclizations are observed in the homolytic reactions of t-BuHgI with CH2=CHCH2YCH2CN [Y = CH2, O, CMe2, C(CO2Et)(2), NCH2CN] and CH2=CHCH2CH2YCH2CN [Y = CH2, O, C(CO2Et)(2)] in Me2SO in the presence of hydriodic acid. Only with Y = C(CO2Et)(2) does the adduct radical, t-BuCH2(C) over dot HCH2YCH2CN, undergo facile 5-exo cyclization in the absence of a proton donor. The other 5-exo and all 6-exo cyclizations require substrate protonation to yield t-BuCH2CH(CH2)(n)YCH2C=NH+ (n = 1, 2), which cyclizes readily to the iminium radical cation followed by electron transfer with I- or t-BuHgI2- to form the imine as a precursor to the cyclopentanone or cyclohexanone upon hydrolysis. For CH2=CHCH2C(CO2Et)(2)CH2CN the formation of the cyclopentanone is dramatically promoted by NH4I in the dark in the absence of any other acid. In this case, where cyclization of the adduct radical occurs readily without substrate activation, protonation of the cyclized iminyl radical allows the electron transfer with I- or t-BuHgI2- to occur with regeneration of t-Bu-.. A similar effect is observed with CH2=CHCH2C(CO2Et)(2)CH2N3 where only a slow reaction is observed upon photolysis with t-BuHgI in the absence of NH4I, although apparently cyclization of t-BuCH2(C) over dot HCH2C(CO2Et)(2)CH2N3 (with loss of N-2) occurs readily. In the presence of NH4I the cyclized aminyl radical can be protonated and the resulting amine radical cation readily reduced by I- or t-BuHgI2- to continue a chain process. With the thioesters CH2=CHCH2YCH2C(O)SPh [Y = O, CH2, CMe2, C(CO2Et)(2)] significant cyclization upon photolysis with t-BuHgX occurred only for Y = C(CO2Et)(2). (C) 1998 John Wiley & Sons, Ltd.
• PATERSON I.; FLEMING I., TETRAHEDRON LETT., 1979, NO 23, 2179-2182
  作者：PATERSON I.、 FLEMING I.

  DOI：——

  日期：——
• PATERSON, IAN, TETRAHEDRON, 44,(1988) N 13, 4207-4219
  作者：PATERSON, IAN

  DOI：——

  日期：——
• α-alkylation and α-alkylidenation of carbonyl compounds by o-silylated enolate phenylthioalkylation
  作者：Ian Paterson

  DOI：10.1016/s0040-4020(01)86667-9

  日期：1988.1

  For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates. In the case of α-alkylation of carbonyl compounds, Lewis-acid (TiCL4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, But, and Me3Si), followed by reductive

  对于羰基旁边的许多反应，使用O-甲硅烷基化的烯醇盐化学方法比第I组金属烯醇盐的相应反应提供了更高的产率和选择性。在羰基化合物，路易斯酸（的TiCl 4的α-烷基化的情况下，4或ZnBr 2）促进了phenylthioalkylation ö -silylated烯醇化物3由α-chlorosulphides 4（R 3 = H，Me中，镨Ñ，镨我，卜吨，和Me 3 Si），然后通过阮内镍从5→6进行还原性硫去除，被认为是此合成上重要的CC键形成步骤的可靠方法。一种替代硫消除途径经由5→7的亚砜可使羰基化合物进行区域和立体控制的α-亚烷基化。苯硫基烷基化反应适用于酮，醛，酯和内酯。