2-(1'-ethoxyethyl)-1-cyclohexanone | 90449-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1'-ethoxyethyl)-1-cyclohexanone
• 英文别名: 2-(1-ethoxyethyl)cyclohexanone；Cyclohexanone, 2-(1-ethoxyethyl)-；2-(1-ethoxyethyl)cyclohexan-1-one
• CAS: 90449-84-6
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: ASYRYAHIFYGVSH-UHFFFAOYSA-N

物化性质

• 沸点：
  236.5±13.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己酮 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2-(1'-ethoxyethyl)-1-cyclohexanone
  参考文献：
  名称：

  路易斯酸活化的烯胺与缩醛或原甲酸三烷基酯的反应

  摘要：

  烯胺很容易由各种羰基化合物制备，在路易斯酸（如 BF3·OEt2）存在下与缩醛或原甲酸三烷基酯反应，以良好的收率得到相应的 β-烷氧基羰基化合物或 α-二烷氧基甲基羰基化合物。二烯胺与缩醛或原甲酸三烷基酯的反应也选择性地以良好的产率得到相应的β,γ-不饱和α-(α-烷氧基烷基)羰基化合物或β,γ-不饱和α-二烷氧基甲基羰基化合物。

  DOI：

  10.1246/bcsj.57.1876

文献信息

• Lewis Acid Mediated Selective Chalcogenalkylation of Silyl Enol Ethers with [O,S]-Acetals
  作者：Antonio L. Braga、Luciano Dornelles、Claudio C. Silveira、Ludger A. Wessjohann

  DOI：10.1055/s-1999-3429

  日期：1999.4

  Silyl enol ethers of ketones were selectively alkylated with [O,S]-acetals mediated by Lewis acid in a Mukaiyama type Aldol reaction. The products were β-alkoxy- and /or β-sulfanyl carbonyl compounds depending on the catalyst employed.

  酮的硅缩酮乙醇醚在Mukaiyama型Aldol反应中，通过Lewis酸介导，选择性地与[O,S]-缩醛进行了烷基化。根据所使用的催化剂，产物为β-烷氧基-和/或β-硫烷基羰基化合物。
• Base-promoted ring expansion of 3-aminopyrimidine-2-thiones into 1,2,4-triazepine-3-thiones
  作者：Anastasia A. Fesenko、Anatoly D. Shutalev

  DOI：10.1016/j.tet.2016.03.082

  日期：2016.5

  A base-promoted ring expansion of 3-amino-4-hydroxyhexahydropyrimidine-2-thiones into 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones has been developed. Experimental data and DFT calculations showed that the reaction proceeded through fast formation of intermediate acyclic isomers of pyrimidines followed by their slow cyclization into triazepines. The starting hydroxypyrimidines were prepared by

  已经开发了3-氨基-4-羟基六氢嘧啶-2-硫酮的碱促进的环扩展成2,4,5,6-四氢-3 H -1,2,4-三氮杂-3-硫酮。实验数据和DFT计算表明，反应是通过快速形成嘧啶的中间体无环异构体，然后缓慢环化为三氮杂s而进行的。通过使α，β-不饱和酮或β-烷氧基酮与HNCS反应，然后用肼处理所获得的β-异硫氰酸根酮来制备起始羟基嘧啶。通过在碱性条件下用H 2 O 2氧化将三氮杂-3-硫酮转化为它们的3-氧代类似物。
• New effective catalysts for Mukaiyama-aldol and -Michael reactions: bismuth trichloride-metallic iodide systems
  作者：Christophe Le Roux、Hafida Gaspard-Iloughmane、Jacques Dubac、Joel Jaud、Pierre Vignaux

  DOI：10.1021/jo00059a040

  日期：1993.3

  Metallic iodide-activated bismuth(III) chloride efficiently catalyzes the Mukaiyama-Aldol and -Michael reactions. Some examples of reactions of silyl enol ethers derived from acetophenone and cyclohexanone (I and 2, respectively) with aldehydes, ketones, acetals, and alpha-enones are given. The cross-over aldolization between 1 and benzaldehyde in the presence of BiCl3-l.5ZnI2 or BiCl3-1.5SnI2 systems (5 % mol) has been carried out quantitatively at -30 and -78-degrees-C, respectively. For this reaction a similar activation has been also observed with antimony(III) chloride. X-ray patterns of catalytic systems show the formation of bismuth(III) iodide by CI/I-exchange reaction between BiCl3 and metallic iodide (NaI, ZnI2, SnI2,...). These results.have been rationalized with a two-step mechanism in which a key feature seems to be the activating role played by BiI3 toward the cleavage of the Bi-chelate intermediate by the chlorosilane formed. Ultrasound activates significantly the catalytic power of these metallic halide systems.
• Makin, S. M.; Kruglikova, R. I.; Tagirov, T. K., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 6, p. 1075 - 1078
  作者：Makin, S. M.、Kruglikova, R. I.、Tagirov, T. K.、Kharitonova, O. V.

  DOI：——

  日期：——
• MAKIN, S. M.;KRUGLIKOVA, R. I.;TAGIROV, T. K.;XARITONOVA, O. V., ZH. ORGAN. XIMII, 1984, 20, N 6, 1182-1185
  作者：MAKIN, S. M.、KRUGLIKOVA, R. I.、TAGIROV, T. K.、XARITONOVA, O. V.

  DOI：——

  日期：——