2-methyl-3-oxo-1-cyclohexene-1-carbaldehyde | 108946-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-oxo-1-cyclohexene-1-carbaldehyde
• 英文别名: 2-Methyl-3-oxocyclohex-1-ene-1-carbaldehyde；2-methyl-3-oxocyclohexene-1-carbaldehyde
• CAS: 108946-97-0
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: NRISBKMZMSQOJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-methyl-3-oxo-1-cyclohexene-1-carbaldehyde 在 二异丁基氢化铝 、 L-脯氨酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (5aS,6S)-6-hydroxy-3,5a-dimethyl-6,7,8,9-tetrahydropyrano[4,3-b]chromen-1-one
  参考文献：
  名称：

  A One-Pot Condensation of Pyrones and Enals. Synthesis of 1H,7H-5a,6,8,9-Tetrahydro-1-oxopyrano[4,3-b][1]benzopyrans

  摘要：

  Condensation of various 6-substituted 4-hydroxypyrones 1 with 1-cyclohexenecarboxaldehydes in the presence of L-proline in ethyl acetate gave high yields of substituted 1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyrans. The reaction presumably occurs via the 1,2-addition of the pyrone with the aldehyde followed by dehydration and then cyclization through a 6 Pi electrocyclic process. A remarkable asymmetric induction was obtained from a stereogenic center (C4) of the cyclohexenecarboxaldehyde [such as (S)-perillaldehyde] to provide only the C5a,7-trans tricyclic pyrone products. On the other hand, condensation of S-(formyloxy)- or 3-hydroxy-2-methyl-1-cyclohexene-carboxaldehydes with pyrones 1 gave mixtures of C5a,6-cis and -trans products. Several of the tricyclic pyrones strongly inhibit acetylcholinesterase activity, DNA synthesis, and tumor cell growth in vitro.

  DOI：

  10.1021/jo970642d
• 作为产物：
  描述：

  2-甲基-2-环己烯-1-酮 在 sodium hydroxide 、 苄基三甲基氢氧化铵 、 对甲苯磺酸 、 臭氧 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 生成 2-methyl-3-oxo-1-cyclohexene-1-carbaldehyde
  参考文献：
  名称：

  Martin, Hans-Dieter; Kummer, Matthias; Martin, Georg, Chemische Berichte, 1987, vol. 120, p. 1133 - 1150

  摘要：

  DOI：

文献信息

• Martin, Hans-Dieter; Kummer, Matthias; Martin, Georg, Chemische Berichte, 1987, vol. 120, p. 1133 - 1150
  作者：Martin, Hans-Dieter、Kummer, Matthias、Martin, Georg、Bartsch, Juergen、Brueck, Dieter、et al.

  DOI：——

  日期：——
• A One-Pot Condensation of Pyrones and Enals. Synthesis of 1<i>H</i>,7<i>H</i>-5a,6,8,9-Tetrahydro-1-oxopyrano[4,3-<i>b</i>][1]benzopyrans
  作者：Duy H. Hua、Yi Chen、Hong-Sig Sin、Maria J. Maroto、Paul D. Robinson、Steven W. Newell、Elisabeth M. Perchellet、James B. Ladesich、Jonathan A. Freeman、Jean-Pierre Perchellet、Peter K. Chiang

  DOI：10.1021/jo970642d

  日期：1997.10.1

  Condensation of various 6-substituted 4-hydroxypyrones 1 with 1-cyclohexenecarboxaldehydes in the presence of L-proline in ethyl acetate gave high yields of substituted 1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyrans. The reaction presumably occurs via the 1,2-addition of the pyrone with the aldehyde followed by dehydration and then cyclization through a 6 Pi electrocyclic process. A remarkable asymmetric induction was obtained from a stereogenic center (C4) of the cyclohexenecarboxaldehyde [such as (S)-perillaldehyde] to provide only the C5a,7-trans tricyclic pyrone products. On the other hand, condensation of S-(formyloxy)- or 3-hydroxy-2-methyl-1-cyclohexene-carboxaldehydes with pyrones 1 gave mixtures of C5a,6-cis and -trans products. Several of the tricyclic pyrones strongly inhibit acetylcholinesterase activity, DNA synthesis, and tumor cell growth in vitro.

表征谱图