2-methyl-1,2,3,4-tetrahydroquinolin-1-amine | 27328-23-0

• 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-methyl-1,2,3,4-tetrahydroquinolin-1-amine
• 英文别名: 2-methyl-3,4-dihydroquinolin-1(2H)-amine；2-methyl-3,4-dihydro-2H-quinolin-1-ylamine；1-Amino-1,2,3,4-tetrahydroquinaldine；2-methyl-3,4-dihydro-2H-quinolin-1-amine
• CAS: 27328-23-0
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: RLBRHMPJAZEEKD-UHFFFAOYSA-N

物化性质

• 沸点：
  279.7±10.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 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：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-丁炔 、 2-methyl-1,2,3,4-tetrahydroquinolin-1-amine 在 [Zr(C5H4NC(Me)(CH2NXyl)2)(NMe2)2] 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以58%的产率得到1,2,4-trimethyl-5,6-dihydro-4H-pyrrolo-[3,2,1-ij] quinoline
  参考文献：
  名称：

  Zirconium Hydrazinediido Complexes Derived from Cyclic Hydrazines and Their Role in the Catalytic Synthesis of 1,7-Annulated Indoles

  摘要：

  Reaction of cyclic 1,1'-disubstituted hydrazines with the bis(dimethylamido)zirconium complex [Zr{(N-Xyl)(2)N-py} (NMe2)(2)] (1) in the presence of dmap yielded the hexacoordinate zirconium hydrazinediido complexes [Zr{(N-Xyl)(2)N-py}(=NNC9H10)(dmap)(2)] (2) and [Zr{(N-Xyl)(2)N-py} (=NNC12H8)(dmap)(2)] (3). Hydrazinediides are thought to be key intermediates in the zirconium-catalyzed reaction of cyclic 1,1'-disubstituted hydrazines and disubstituted alkynes to yield 1,7-annulated indoles. Their basic structural motif is found in 5-HT3 receptor antagonists such as Cilansetron.

  DOI：

  10.1021/om301235d
• 作为产物：
  描述：

  1-Nitroso-1,2,3,4-tetrahydrochinaldin 在 四氯化钛 、 magnesium 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以83%的产率得到2-methyl-1,2,3,4-tetrahydroquinolin-1-amine
  参考文献：
  名称：

  Landriani; Barlocco; Pinna, Il Farmaco, 1989, vol. 44, # 11, p. 1059 - 1068

  摘要：

  DOI：

文献信息

• Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles
  作者：Shuguang Zhou、Jinhu Wang、Lili Wang、Kehao Chen、Chao Song、Jin Zhu

  DOI：10.1021/acs.orglett.6b01805

  日期：2016.8.5

  Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C–H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of

  本文报道了Co（III）催化的，内部和末端炔烃相容的吲哚合成方案。的Ñ -氨基（肼）基团面授不同的，多样化反应性模式用于定向C-H官能化/环化反应。显着的合成特征包括对间取代的芳基肼的区域选择性，对链支化的末端炔烃的区域选择性，在C2硅烷化的吲哚衍生物上通过C2-去甲硅烷基化正式引入炔属单元，通过连续的C3-衍生化和C2对区域选择性进行正式转化-去甲硅烷基化过程，以及线性链末端炔烃的形式键迁移。
• [DE] 8-AMINO-1,2,3,4-TETRAHYDROCHINOLINE ALS KUPPLER IN FÄRBEMITTELN<br/>[EN] 8-AMINO-1,2,3,4-TETRAHYDROQUINOLINES AS COUPLERS IN DYES<br/>[FR] 8-AMINO-1,2,3,4-TETRAHYDROQUINOLINES SERVANT DE COPULATEURS POUR DES COLORANTS
  申请人：HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN

  公开号：WO1994028863A1

  公开（公告）日：1994-12-22

  (DE) Die Erfindung betrifft Mittel zum Färben von keratinhaltigen Fasern, insbesondere menschlichen Haaren, die als Entwicklerkomponente ein p-Aminophenol oder ein p-Phenylendiamin und als Kupplerkomponente ein 8-Amino-1,2,3,4-tetrahydrochinolin enthalten.(EN) The invention pertains to dyes for keratin-containing fibers, especially human hair, said dyes containing a p-aminophenol or a p-phenylenediamine as developer component and an 8-amino-1,2,3,4-tetrahydroquinoline as coupler component.(FR) L'invention concerne des agents permettant de colorer des fibres contenant de la kératine, notamment des cheveux naturels, qui contiennent comme révélateur un p-aminophénol ou une p-phénylènediamine et comme copulateur une 8-amino-1,2,3,4-tétrahydroquinoline.

  该发明涉及用于含有角质素的纤维，特别是人类 hair的染料，这些染料含有一个 p-aminophenol 或 p-phenylendiamin 的 developer 成分，以及一个 8-amino-1,2,3,4-tetrahydroquinoline 的 coupler 成分。该发明涉及用于染色含有角质素的纤维，特别是人类头发的染料。这些染料包含一个 p-aminophenol 或 p-phenylendiamin 作为起 Developer 作用的成分，以及一个 8-amino-1,2,3,4-tetrahydroquinoline 作为配对成分。该发明涉及用于染色含有角质素的纤维和 Natural hair，尤其是人类头发的染料。这些染料中含有一个 p-aminophenol 或 p-phenylendiamin 作为 developer 成分，并且含有一个 8-amino-1,2,3,4-tetrahydroquinoline 作为 coupler 成分。
• 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.
• ?-Dimethylaminomethylene-?-thiobutyrolactone and synthesis of heterocyclic derivatives
  作者：G. P. Tokmakov

  DOI：10.1007/bf01165438

  日期：1996.2
• SHORINA, N. V.;GOLUBEVA, G. A.;SVIRIDOVA, L. A.;TOROCHESHNIKOV, V. N., XIMIYA GETEROTSIKL. SOED.,(1990) N, S. 332-336
  作者：SHORINA, N. V.、GOLUBEVA, G. A.、SVIRIDOVA, L. A.、TOROCHESHNIKOV, V. N.

  DOI：——

  日期：——