4-叔丁基-2-甲基-1,2,3,4-四氢喹啉 | 152536-57-7

• 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
• 中文名称: 4-叔丁基-2-甲基-1,2,3,4-四氢喹啉
• 英文名称: 4-(1,1-dimethylethyl)-1,2,3,4-tetrahydro-2-methylquinoline
• 英文别名: 4-tert-Butyl-1,2,3,4-tetrahydro-2-methylquinoline；4-tert-Butyl-2-methyl-1,2,3,4-tetrahydroquinoline
• CAS: 152536-57-7
• 化学式: C₁₄H₂₁N
• 分子量: 203.327
• InChiKey: VJRRHQPTVXXGST-UHFFFAOYSA-N

物化性质

• 沸点：
  283.7±10.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(1,1-二甲基乙基)-2-甲基喹啉 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以56%的产率得到4-叔丁基-2-甲基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  tert-Butylation of Quinolinium Cations and Quinoline N-Oxides by tert-Butylmercury Halides

  摘要：

  In the presence of t-BuHgCl/KI the radical cations formed by the addition of tert-butyl radicals to C-2 of the quinolinium cation react in Me(2)SO by proton loss followed by one-electron oxidation (1a, R = H, Me, Cl). For the N-methyl, or N-methoxyquinolinium cations proton loss is not observed and the radical cations react by one-electron reduction (1b, R = Me, Cl; Ic, R = Me), With quinoline N-oxide and its 4-substituted derivatives the C-2 adduct radicals (1d, R = H, Me, Cl) are deprotonated by DABCO to yield after one-electron oxidation the 2-tert-butylquinoline N-oxides. The adduct radical cations formed by t-Bu(.) addition at the C-4 of quinolinium ions 2 seldom lose the C-4 proton but react by reduction, hydration, or in the case of 2-chloroquinoline N-oxide, dimerization. The loss of the proton from the 2-adducts 1 but not from the 4-adducts 2 seems to be stereoelectronic in origin. With N-methylquinolinium cation the addition of t-Bu(.) occurs selectively (>90%) at C-4 in contrast to the low selectivity observed in addition to quinolinium ion itself. However, with N-methoxyquinolinium perchlorate the major reaction products (70-90%) result from the addition of t-Bu(.) at C-2.

  DOI：

  10.1021/jo00122a013

文献信息

• Russell, Glen A.; Rajaratnam, Rajine; Wang, Lijuan, Journal of the American Chemical Society, 1993, vol. 115, # 23, p. 10596 - 10604
  作者：Russell, Glen A.、Rajaratnam, Rajine、Wang, Lijuan、Shi, Bing Zhi、Kim, Byeong Hyu、Yao, Ching Fa

  DOI：——

  日期：——
• tert-Butylation of Quinolinium Cations and Quinoline N-Oxides by tert-Butylmercury Halides
  作者：Glen A. Russell、Lijuan Wang、Ching-Fa Yao

  DOI：10.1021/jo00122a013

  日期：1995.9

  In the presence of t-BuHgCl/KI the radical cations formed by the addition of tert-butyl radicals to C-2 of the quinolinium cation react in Me(2)SO by proton loss followed by one-electron oxidation (1a, R = H, Me, Cl). For the N-methyl, or N-methoxyquinolinium cations proton loss is not observed and the radical cations react by one-electron reduction (1b, R = Me, Cl; Ic, R = Me), With quinoline N-oxide and its 4-substituted derivatives the C-2 adduct radicals (1d, R = H, Me, Cl) are deprotonated by DABCO to yield after one-electron oxidation the 2-tert-butylquinoline N-oxides. The adduct radical cations formed by t-Bu(.) addition at the C-4 of quinolinium ions 2 seldom lose the C-4 proton but react by reduction, hydration, or in the case of 2-chloroquinoline N-oxide, dimerization. The loss of the proton from the 2-adducts 1 but not from the 4-adducts 2 seems to be stereoelectronic in origin. With N-methylquinolinium cation the addition of t-Bu(.) occurs selectively (>90%) at C-4 in contrast to the low selectivity observed in addition to quinolinium ion itself. However, with N-methoxyquinolinium perchlorate the major reaction products (70-90%) result from the addition of t-Bu(.) at C-2.