2,6-dimethyl-1,4-cyclohexadione | 14384-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dimethyl-1,4-cyclohexadione
• 英文别名: 2,6-dimethylcyclohexanedione；2,6-dimethyl-1,4-cyclohexanedione；2,6-Dimethylcyclohexane-1,4-dione
• CAS: 14384-30-6
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: DJTNCJGSGMJLQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-1,4-cyclohexadione 在 双氧水 、 L-Selectride 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 29.0h， 生成 (7α,8α,9α)-7,9-dimethyl-1,4-dioxaspiro[4.5]decan-8-ol
  参考文献：
  名称：

  Synthetic studies directed toward the naturally occurring acyl tetramic acids. 1. Convergent total synthesis of (.+-.)-tirandamycin A

  摘要：

  DOI：

  10.1021/ja00278a031
• 作为产物：
  描述：

  7,9-二甲基-1,4-二氧杂-螺[4.5]癸烷-8-酮 在 盐酸 作用下， 反应 1.0h， 以90%的产率得到2,6-dimethyl-1,4-cyclohexadione
  参考文献：
  名称：

  1,4-环己二酮和仲芳香胺的缩合。烷基二芳胺和三芳胺的形成

  摘要：

  1,4-环己二酮与N-烷基芳基胺缩合得到N-烷基-N-芳基苯胺，与二芳基胺缩合得到三芳基胺。该反应提出了一种涉及 1,4-二酮单烯胺脱水的机制。相对于 Hammet σ 值绘制的竞争反应中取代 N-乙基苯胺的相对比率给出 -2.0 作为 ρ 值。然而，在单独的反应中，产率有不同的趋势，即与对氯和对硝基衍生物反应的容易程度。这种差异是根据用作实际催化剂的胺的共轭酸的酸度来解释的。

  DOI：

  10.1246/bcsj.57.1586

文献信息

• New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives
  作者：Martin R. Bryce、Stephen R. Davies、Andrew M. Grainger、Michael B. Hursthouse、Mohammed Mazid、Rainer Bachmann、Fabian Gerson、Jonas Hellberg

  DOI：10.1021/jo00032a017

  日期：1992.3

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.
• HAGA, KAZUO;OOHASHI, MASAYUKI;KANEKO, RYOHEI, BULL. CHEM. SOC. JAP., 1984, 57, N 6, 1586-1590
  作者：HAGA, KAZUO、OOHASHI, MASAYUKI、KANEKO, RYOHEI

  DOI：——

  日期：——
• Synthetic studies directed toward the naturally occurring acyl tetramic acids. 1. Convergent total synthesis of (.+-.)-tirandamycin A
  作者：Robert K. Boeckman、John E. Starrett、David G. Nickell、P. E. Sum

  DOI：10.1021/ja00278a031

  日期：1986.9
• Condensations of 1,4-Cyclohexanediones and Secondary Aromatic Amines. The Formation of Alkyldiarylamines and Triarylamines
  作者：Kazuo Haga、Masayuki Oohashi、Ryohei Kaneko

  DOI：10.1246/bcsj.57.1586

  日期：1984.6

  Condensation of 1,4-cyclohexanedione with N-alkylarylamines gives N-alkyl-N-arylanilines, and that with diarylamines gives triarylamines. A mechanism involving dehydration of monoenamines of the 1,4-dione is proposed for the reaction. Relative rates of substituted N-ethylanilines on competitive reactions plotted vs. Hammet’s σ values gave −2.0 as the ρ value. In separate reactions, however, a different

  1,4-环己二酮与N-烷基芳基胺缩合得到N-烷基-N-芳基苯胺，与二芳基胺缩合得到三芳基胺。该反应提出了一种涉及 1,4-二酮单烯胺脱水的机制。相对于 Hammet σ 值绘制的竞争反应中取代 N-乙基苯胺的相对比率给出 -2.0 作为 ρ 值。然而，在单独的反应中，产率有不同的趋势，即与对氯和对硝基衍生物反应的容易程度。这种差异是根据用作实际催化剂的胺的共轭酸的酸度来解释的。