2,8-dimethyl-5-nitro-4-chloroquinoline | 157493-69-1

• 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: 2,8-dimethyl-5-nitro-4-chloroquinoline
• 英文别名: 4-chloro-2,8-dimethyl-5-nitroquinoline；4-chloro-5-nitro-2,8-dimethylquinoline
• CAS: 157493-69-1
• 化学式: C₁₁H₉ClN₂O₂
• mdl: MFCD04061320
• 分子量: 236.658
• InChiKey: ADJHRRYYNVYIGN-UHFFFAOYSA-N

物化性质

• 沸点：
  370.1±37.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,8-dimethyl-5-nitro-4-chloroquinoline 在 铁粉 、 溶剂黄146 作用下， 以 邻二甲苯 为溶剂， 反应 8.5h， 生成 5-amino-2,8-dimethyl-4-(p-methylphenylamino)quinoline
  参考文献：
  名称：

  Komissarov, V. N.; Gruzdeva, E. N.; Kharlanov, V. A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 10.2, p. 1688 - 1691

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-2,8-二甲基喹啉 在 硫酸 、 硝酸 作用下， 生成 2,8-dimethyl-5-nitro-4-chloroquinoline
  参考文献：
  名称：

  Synthesis of 4,5-Bis(Dimethylamino)Quinolines and the Dual Direction of their Protonation

  摘要：

  A study on the synthesis of derivatives of 4,5-bis(dimethylamino)quinoline, which is a quinoline analog of 1,8-bis(dimethylamino)naphthalene (also known by its trade name Proton Sponge) was carried out. The first two representatives of this series were obtained. Depending on the aggregate state, solvent, and structural features, these compounds may be protonated either at the quinoline heteroatom or peri-NMe2 groups.

  DOI：

  10.1007/s10593-013-1380-4

文献信息

• New method for the synthesis of β-tropolones: Structures of condensation products of o-quinones with 2-methylquinolines and the mechanism of their formation
  作者：V. I. Minkin、S. M. Aldoshin、V. N. Komissarov、I. V. Dorogan、Yu. A. Sayapin、V. V. Tkachev、A. G. Starikov

  DOI：10.1007/s11172-006-0547-x

  日期：2006.11

  containing the tertiary amino group at position 4 with quinone 14 is accompanied by the formation of derivatives of a new heterocyclic system, viz., 4,6-dioxo-2-azabicyclo[3.3.0]octa-2,7-diene N-oxide. The molecular and crystal structures of two 5,7-di(tert-butyl)-3-hydroxy-2-(quinolin-2-yl)tropolones and two dioxoazabicyclooctadiene N-oxides, as well as of the preparatively isolated intermediate of the first

  开发了一种基于 2-甲基喹啉衍生物与 3,5-二(叔丁基)-1,2-苯醌和 4,6-二(叔-丁基)-3-硝基-1,2-苯醌 (14)。通过量子化学方法 (DFT B3LYP/6-31G**) 研究了多步反应产生 β-tropolone 的机制及其互变异构现象。在 4 位含有叔氨基的 2-甲基喹啉衍生物与醌 14 的反应伴随着新杂环系统衍生物的形成，即 4,6-二氧代-2-氮杂双环 [3.3.0]octa- 2,7-二烯N-氧化物。两种 5,7-二(叔丁基)-3-羟基-2-(quinolin-2-yl)tropolones 和两种二氧氮杂双环辛二烯 N-氧化物的分子和晶体结构，
• Synthesis, structure, and photoisomerization of derivatives of 2-(2-quinolyl)-1,3-tropolones prepared by the condensation of 2-methylquinolines with 3,4,5,6-tetrachloro-1,2-benzoquinone
  作者：Yury A. Sayapin、Bang Nghia Duong、Vitaly N. Komissarov、Igor V. Dorogan、Nadezhda I. Makarova、Inna O. Bondareva、Valery V. Tkachev、Gennady V. Shilov、Sergey M. Aldoshin、Vladimir I. Minkin

  DOI：10.1016/j.tet.2010.08.077

  日期：2010.11

  series of novel derivatives of the 1,3-tropolone (β-tropolone) system—2-(2-quinolyl)-5,6,7-trichloro-1,3-tropolones and 2-(2-quinolyl)-4,5,6,7-tetrachloro-1,3-tropolones have been prepared by the acid-catalyzed reaction of 2-methylquinolines with 3,4,5,6-tetrachloro-1,2-benzoquinone. The molecular structures of two compounds, 2-(4-chloro-6,8-dimethyl-5-nitro-2-quinolyl)-5,6,7-trichloro-1,3-tropolone 8

  1,3-tropolone（β-tropolone）系统的一系列新型衍生物—2-（2-喹啉基）-5,6,7-三氯-1,3-对苯二酚和2-（2-喹啉基）-4通过2-甲基喹啉与3,4,5,6-四氯-1,2-苯醌的酸催化反应，制备了1,2,5,6,7-四氯-1,3-对苯二酚。2-（4-氯-6,8-二甲基-5-硝基-2-喹啉基）-5,6,7-三氯-1,3-羟戊酮8和2-（4-氯-7，8-二甲基-5-硝基-2-喹啉基）-4，5，6，7-四氯-1，3-羟戊酮9已经用X射线晶体学测定。根据进行的DFT B3LYP / 6-311 ++ G ***计算，β-对苯二酚8和9的互变异构（OH）和（NH）形式几乎等同于能量，后者在极性介质中更稳定。2-（2-喹啉基）-1,3-对苯二酚在庚烷溶液中的光解导致可旋转的电环重排，导致形成3- [2（1 H）-喹啉基]的E-和Z-异构体的混合物-双环[3.2.0]庚-6-en-2
• Synthesis and Structure of New 2-(2-Quinolyl)-1,3-tropolone Derivatives
  作者：Yu. A. Sayapin、V. N. Komissarov、V. I. Minkin、V. V. Tkachev、S. M. Aldoshin、G. V. Shilov

  DOI：10.1007/s11178-005-0379-4

  日期：2005.10

  4,6-Di-tert-butyl-3-nitro-1,2-benzoquinone reacts with substituted 2-methylquinolines to give the corresponding 2-(2-quinolyl)-4-nitro-1,3-tropolones and 2-(2-quinolyl)-1,3-tropolones.

  4,6-二叔丁基-3-硝基-1,2-苯醌与取代的 2-甲基喹啉反应生成相应的 2-(2-喹啉基)-4-硝基-1,3-三苯丙酮和 2-(2-喹啉基)-1,3-三苯丙酮。
• Komissarov, Vitalii N.; Bang, Dyong Nghia; Minkin, Vladimir I., Mendeleev Communications, 2003, vol. 13, # 5, p. 219 - 221
  作者：Komissarov, Vitalii N.、Bang, Dyong Nghia、Minkin, Vladimir I.、Aldoshin, Sergei M.、Tkachev, Valery V.、Shilov, Gennady V.

  DOI：——

  日期：——
• 4,5-Bis(dimethylamino)quinolines: Proton Sponge versus Azine Behavior
  作者：Olga V. Dyablo、Elena A. Shmoilova、Alexander F. Pozharskii、Valery A. Ozeryanskii、Oleg N. Burov、Zoya A. Starikova

  DOI：10.1021/ol301777s

  日期：2012.8.17

  Two first representatives, 5 and 6, of the still unknown 4,5-bis(dimethylamino)quinoline have been synthesized and studied. While the former, being protonated either at the peri-NMe2 groups or at the ring nitrogen, has been shown to display properties of both a proton sponge and azine, its counterpart 6 behaves exclusively as azine giving only a quinolinium salt.