6-methyl-1-nitroso-1,2,3,4-tetrahydro-quinoline | 99068-04-9

• 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: 6-methyl-1-nitroso-1,2,3,4-tetrahydro-quinoline
• 英文别名: 6-Methyl-1-nitroso-1,2,3,4-tetrahydro-chinolin；6-methyl-1-nitroso-3,4-dihydro-2H-quinoline
• CAS: 99068-04-9
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: QMYWMBKZLHGACT-UHFFFAOYSA-N

物化性质

• 沸点：
  349.0±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-1-nitroso-1,2,3,4-tetrahydro-quinoline 在 甲醇 、 硫酸 、 溶剂黄146 、 锌 作用下， 生成 2,3,5-Trimethyl-1,7-trimethylenindol
  参考文献：
  名称：

  Kost et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3977,3981; engl. Ausg. S. 3937, 3940

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基-1,2,3,4-四氢喹啉 在 盐酸 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 生成 6-methyl-1-nitroso-1,2,3,4-tetrahydro-quinoline
  参考文献：
  名称：

  通过 N-亚硝基苯胺的连续选择性 CH 官能化快速获得多取代四氢咔唑-4-酮

  摘要：

  在此，我们开发了一种Rh(III)催化N-亚硝基苯胺和碘鎓叶立德的C-H活化策略，构建新型四氢咔唑-4-酮支架，为连续的C-H功能化（例如烷基化、烯基化）提供了有价值的模板四氢咔唑-4-酮的C 5位上的酰胺化和（杂）芳基化与不同的偶联配偶体。四氢咔唑-4-酮衍生物的克级合成和进一步转化为昂丹司琼及其类似物证明了该方案的实用性，使得生物活性分子的简洁和多样化的构建成为可能。

  DOI：

  10.1002/cjoc.202300015

文献信息

• Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of N-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1H)-One Scaffolds
  作者：Lingjun Liu、Jiyuan Li、Wenhao Dai、Feng Gao、Kaixian Chen、Yu Zhou、Hong Liu

  DOI：10.3390/molecules25020268

  日期：——

  [3+3] cyclization of N-nitrosoanilines with cyclopropenones has been achieved. This protocol features short reaction time and atom-economical combination without extra additives, which can be further applied in the construction of privileged heterocyclic compounds in pharmaceutical chemistry.

  通过Rh(III)-催化氧化还原-中性[3+3]环化N-亚硝基苯胺与环丙烯酮的喹啉-4(1H)-one支架的无痕方法已经实现。该方案反应时间短，原子经济结合，无需额外添加剂，可进一步应用于药物化学中特权杂环化合物的构建。
• Bamberger; Wulz, Chemische Berichte, 1891, vol. 24, p. 2051
  作者：Bamberger、Wulz

  DOI：——

  日期：——
• Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma
  作者：Dominique Paris、Michel Cottin、Patrice Demonchaux、Guy Augert、Pierre Dupassieux、Patrick Lenoir、Michael J. Peck、Daniel Jasserand

  DOI：10.1021/jm00004a013

  日期：1995.2

  A series of pyrrolo[3,2,1-ij]quinoline derivatives was synthesized and evaluated for their in vitro and in vivo activities against histamine, platelet activating factor (PAF), and leukotrienes which are recognized to be of importance in asthma. The structure-activity relationship studies have shown that the optimum moiety on the 1-position of the pyrroloquinoline nucleus is a 2-[4-(4-methyl-2-pyridinyl)-1-piperazinyl]ethyl chain in conjunction with a methyl group on the 2-position for potent antagonism of both histamine and PAF. The introduction of substituents on the 8- and 4-positions was also investigated in order to increase the potency of 5-lipoxygenase inhibition while retaining or improving the activities against histamine and PAF. This series is exemplified by 4-n-butyl-5,6-dihydro-8-hydroxy-2-methyl-1-[2-[4-(4-methyl- 2-pyridinyl)-1-piperazinyl]ethyl]-4H-pyrrolo[3,2,1-ij]quinoline (24, KC 11404) which was found to be active against all three of the selected mediators. Compound 24 was found to be orally active in guinea pig models against the histaminic phase of antigen-induced bronchospasm and PAF-induced bronchoconstriction (ED(50) = 1.9 and 2.1 mu mol/kg, respectively). When tested against the leukotriene-dependent phase of the antigen-induced bronchoconstriction, compound 24 showed the same potency as zileuton.
• Kost et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3977,3981; engl. Ausg. S. 3937, 3940
  作者：Kost et al.

  DOI：——

  日期：——
• Rapid access to polysubstituted tetrahydrocarbazol‐4‐ones via sequential selective C−H functionalization from <i>N</i> ‐nitrosoanilines
  作者：Chan Li、Yanchen Yang、Feifei Fang、Chaoyi Liu、Chunpu Li、Dechuan Wang、Hong Liu

  DOI：10.1002/cjoc.202300015

  日期：——

  have developed a strategy of Rh(III)-catalyzed C—H activation of N-nitrosoanilines and iodonium ylides to construct novel tetralydrocarbzol-4-one scaffolds, which provided valuable templates for sequential C—H functionalization such as alkylation, alkenylation, amidation and (hetero)arylation at C5-position of tetralydrocarbzol-4-one with different coupling partners. Gram-scale synthesis and further transformations

  在此，我们开发了一种Rh(III)催化N-亚硝基苯胺和碘鎓叶立德的C-H活化策略，构建新型四氢咔唑-4-酮支架，为连续的C-H功能化（例如烷基化、烯基化）提供了有价值的模板四氢咔唑-4-酮的C 5位上的酰胺化和（杂）芳基化与不同的偶联配偶体。四氢咔唑-4-酮衍生物的克级合成和进一步转化为昂丹司琼及其类似物证明了该方案的实用性，使得生物活性分子的简洁和多样化的构建成为可能。