3-[1-(Diethylamino)ethyl]cyclohexan-1-one | 132377-12-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[1-(Diethylamino)ethyl]cyclohexan-1-one
• 英文别名: 3-[1-(diethylamino)ethyl]cyclohexan-1-one
• CAS: 132377-12-9；132377-13-0
• 化学式: C₁₂H₂₃NO
• 分子量: 197.321
• InChiKey: AYWJNHBTMKBYJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 三乙胺 以 乙腈 为溶剂， 以3%的产率得到环己酮
  参考文献：
  名称：

  Photoreactivity of α,gb-unsaturated carbonyl compounds. 3. Radical-ion cidnp during irradiation of cyclohexenones with dabco.

  摘要：

  DOI：

  10.1016/s0040-4039(01)80061-7

文献信息

• A reinvestigation of the reactions occurring upon photoexcitation of cyclohexenone in the presence of triethylamine
  作者：David I. Schuster、Anthony M. Insogna

  DOI：10.1021/jo00005a039

  日期：1991.3

  It had been previously reported that the distribution of products from irradiation of cyclohexenone (CH) in the presence of triethylamine (TEA) required the intermediacy of a triplet excimer intermediate derived from the enone. Reinvestigation of this reaction has given results removing the necessity of postulating such an intermediate. Specifically, the reaction results in the products previously reported, namely cyclohexanone, photodimers (two major, two minor), and a pair of 1:1 enone-amine adducts, as well as previously unobserved products from reductive dimerization of the enone (3-(3-oxocyclohexyl)cyclohexanone) and from condensation of two enone and one amine moieties. The photodimer yields decreased dramatically as the amine concentration was increased, and the product ratios were dependent on the CH concentration, findings which are contrary to the earlier report but understandable if there is a competition between TEA and ground-state CH for capture of monomeric CH triplets. The mechanism for formation of the products derived from interaction of TEA involves an initial electron-transfer step to give a pair of radical ions, followed immediately by proton transfer to a ketyl and an alpha-aminoalkyl radical, which yield the observed products by subsequent radical combination and H-abstraction reactions. These results are consistent with published laser flash kinetic data from this laboratory, and earlier studies of the photochemical behavior of other ketones in the presence of amines.
• Photoreactivity of .alpha.,.beta.-unsaturated carbonyl compounds. Competitive 2-cyclohexenone dimerization and adduct formation with triethylamine
  作者：Norbert J. Pienta、Jennifer E. McKimmey

  DOI：10.1021/ja00384a048

  日期：1982.10
• Photoreactivity of α,gb-unsaturated carbonyl compounds. 3. Radical-ion cidnp during irradiation of cyclohexenones with dabco.
  作者：David W. Smith、Norbert J. Pienta

  DOI：10.1016/s0040-4039(01)80061-7

  日期：1984.1