1,2,2,4,6-pentamethyl-1,2-dihydroquinoline | 46387-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,2,4,6-pentamethyl-1,2-dihydroquinoline
• 英文别名: 1,2,2,4,6-pentamethyl-1,2-dihyroquinoline；1,2,2,4,6-pentamethyl-1,2-dihydro-quinoline；1,2,2,4,6-Pentamethyl-1,2-dihydro-chinolin；1,2,2,4,6-pentamethylquinoline
• CAS: 46387-10-4
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: PASKPJFYIMJNGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  150-152 °C(Press: 12 Torr)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,2,4,6-pentamethyl-1,2-dihydroquinoline 在 水 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 4-hydroxy-1,2,2,4,6-pentamethyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  摘要：

  Photolysis of 2,2,4,6-tetramethyl- (1) and 1,2,2,4,6-pentamethyl-1,2-dihydroquinoline (2) in methanolic alkali yields only 4-methoxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline in the former case and a mixture of 4-methoxy- and 4-hydroxy-1,2,2,4,6-pentamethyl- 1,2,3,4-tetrahydroquinoline in the latter case. This result was rationalized by the existence of two resonance structures of an intermediate cation, viz., carbocationic and ortho-quinomethaneiminium species. The cation from 1 reacts with an alkali in the ortho-quinomethaneiminium form, and the cation generated from 2 reacts in the carbocationic form.

  DOI：

  10.1023/a:1021659809874
• 作为产物：
  描述：

  2,2,4,6-四甲基-1H-喹啉 、 碘甲烷 生成 1,2,2,4,6-pentamethyl-1,2-dihydroquinoline
  参考文献：
  名称：

  1,2,2,4,6-pentamethyl-1,2-dihydroquinoline 光解产生的碳正离子对叠氮离子的反应性

  摘要：

  通过脉冲（常规和激光）和稳态光解技术研究了叠氮离子与 1,2,2,4,6-五甲基-1,2-二氢喹啉在甲醇中的光解过程中产生的碳正离子的反应。叠氮化物离子的加合物通过 1 H NMR 光谱表征。考虑到甲醇和叠氮化物离子添加到碳正离子之间的竞争，对实验结果进行了解释。叠氮离子与碳正离子 (kAz) 反应的速率常数是在 2-48 °C 下在 [N3-]0 浓度范围从 2·10-7 到 0.1 mol L-1 的不同离子浓度范围内测量的。溶液的强度 (μ)。由此产生的 kAz 值比扩散控制反应的值低一个数量级以上，从 3.2·108 (μ = 0) 到 4.5·106 L mol-1 s-1 (μ = 0. 8 mol L–1) 在 NaClO4 (18 °C) 存在下。叠氮离子与碳正离子加成的活化能为 21 kJ mol-1，比碳正离子与甲醇反应的活化能低 12 kJ mol-1。从二氢喹啉光解

  DOI：

  10.1023/b:rucb.0000037847.04785.bc

文献信息

• Knoevenagel; Baehr, Chemische Berichte, 1922, vol. 55, p. 1926
  作者：Knoevenagel、Baehr

  DOI：——

  日期：——
• Knoevenagel, Chemische Berichte, 1921, vol. 54, p. 1726;
  作者：Knoevenagel

  DOI：——

  日期：——
• ——
  作者：T. D. Nekipelova、L. N. Kurkovskaya、I. I. Levina、V. S. Shishkov、V. A. Kuzmin

  DOI：10.1023/a:1011369030104

  日期：——

  Steady-state photolysis products of 6- and 8-substituted 2,2,4-trimethyl- 1,2-dihydroquinolines in water and lower alcohols were identified by III NMR. [it the case of electron-donor substituents, the solvent molecule is added to the double bond of the heterocycle affording the corresponding 4-hydroxy- or 4-alkoxytetrahydroquinolines. Nitro-substituted dihydroquinolines are photostable. The addition of EtOH and (PrOH)-O-n occurs only in the presence of water to give a mixture of alkoxy- and hydroxy-adducts. A reaction scheme is suggested.
• Knoevenagel; Baehr, Chemische Berichte, 1922, vol. 55, p. 1922
  作者：Knoevenagel、Baehr

  DOI：——

  日期：——
• ——
  作者：T. D. Nekipelova、L. N. Kurkovskaya、I. I. Levina

  DOI：10.1023/a:1021659809874

  日期：——

  Photolysis of 2,2,4,6-tetramethyl- (1) and 1,2,2,4,6-pentamethyl-1,2-dihydroquinoline (2) in methanolic alkali yields only 4-methoxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline in the former case and a mixture of 4-methoxy- and 4-hydroxy-1,2,2,4,6-pentamethyl- 1,2,3,4-tetrahydroquinoline in the latter case. This result was rationalized by the existence of two resonance structures of an intermediate cation, viz., carbocationic and ortho-quinomethaneiminium species. The cation from 1 reacts with an alkali in the ortho-quinomethaneiminium form, and the cation generated from 2 reacts in the carbocationic form.