trans-2-methyl-N-phenyl-1,2,3,4-tetrahydroquinolin-4-amine | 1026-05-7

• 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
• 英文名称: trans-2-methyl-N-phenyl-1,2,3,4-tetrahydroquinolin-4-amine
• 英文别名: trans-2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline；trans-4-anilino-2-methyl-1,2,3,4-tetrahydroquinoline；4-anilino-2-methyl-1,2,3,4-tetrahydroquinoline；2-methyl-4-N-phenyltetrahydroquinolin-4-amine；(+/-)-(2t-methyl-1,2,3,4-tetrahydro-[4r]quinolyl)-phenyl-amine；(+/-)-(2t-Methyl-1,2,3,4-tetrahydro-[4r]chinolyl)-phenyl-amin；trans-2-methyl-N-phenyl-1,2,3,4-tetrahydro-4-quinolinamine；(2S,4S)-2-methyl-N-phenyl-1,2,3,4-tetrahydroquinolin-4-amine
• CAS: 1026-05-7；26343-37-3；26343-40-8
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: FTECJLOPKLYFII-LRDDRELGSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  400.4±44.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 trans-2-methyl-N-phenyl-1,2,3,4-tetrahydroquinolin-4-amine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到(+/-)-trans-4-Anilino-1-benzoyl-2-methyl-1,2,3,4-tetrahydrochinolin
  参考文献：
  名称：

  Tetrahydroquinoline derivatives as CRTH2 antagonists

  摘要：

  A series of tetrahydroquinoline-derived inhibitors of the CRTH2 receptor was discovered by a high throughput screen. Optimization of these compounds for potency and pharmacokinetic properties led to the discovery of potent and orally bioavailable CRTH2 antagonists. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.094
• 作为产物：
  描述：

  2-苯胺基丙酸 在 DPZ 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以55.556%的产率得到
  参考文献：
  名称：

  一种可见光催化氨基酸脱羧合成1,2,3,4-四 氢喹啉类化合物的方法

  摘要：

  本发明涉及一种可见光催化氨基酸脱羧合成1,2,3,4‑四氢喹啉类化合物的方法，其特征在于，在空气气氛下，将式Ⅰ所示的N‑苯基氨基酸类化合物、有机光催化剂DPZ和4Å分子筛溶于有机溶剂中，在可见光照射下于20―30℃搅拌反应至少5h，分离纯化，即得到式Ⅱ所示的四氢喹啉类化合物；式Ⅰ和式Ⅱ中，R代表氢、卤素、烷基、苯基和烷氧基中的任意一种，R1代表氢、甲基、正丙基和苯基中的任意一种,alkyl代表甲基、乙基、正丁基或苄基，aryl代表取代苯基或4‑叔丁基苯基。该方法底物简单，反应条件温和，催化剂用量少，收率高且无金属参与。

  公开号：

  CN108017580B

文献信息

• Assembly of Substituted 2-Alkylquinolines by a Sequential Palladium-Catalyzed CN and CC Bond Formation
  作者：Yoshio Matsubara、Saori Hirakawa、Yoshihiro Yamaguchi、Zen-ichi Yoshida

  DOI：10.1002/anie.201102076

  日期：2011.8.8

  Diversity: A range of substituted 2‐alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium‐catalyzed CN and CC bond formation, followed by palladium‐catalyzed aromatization, and results in the formation of the desired compounds in one step.

  多样性：可以通过采用温和的反应条件的常规有效合成方法来制备一系列取代的2-烷基喹啉（请参阅方案）。合成是基于连续的钯催化的C ^  N和C  C键的形成，随后进行钯催化的芳构化，并导致在一个步骤中形成所需的化合物。
• Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives
  作者：Xiao-dong Jia、Yan Ren、Cong-de Huo、Wen-Juan Wang、Xiang-Ning Chen、Xiao-Lan Xu、Xi-cun Wang

  DOI：10.1016/j.tetlet.2010.10.106

  日期：2010.12

  A tandem cyclization of imines with N-vinyllactams induced by TBPA+ was investigated, and a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines were synthesized based on a domino process in which N-vinyllactams serve as an acetaldehyde surrogate. A single electron transfer mechanism was proposed and radical cation salt acts as both a Lewis acid and one electron oxidant to induce such transformation

  研究了由TBPA +诱导的亚胺与N-乙烯基内酰胺的串联环化反应，并基于其中N-乙烯基内酰胺起作用的多米诺过程，合成了一系列2-甲基-4-苯胺基-1,2,3,4-四氢喹啉作为乙醛的替代物。提出了单一的电子转移机制，自由基阳离子盐既充当路易斯酸又充当一种电子氧化剂来诱导这种转变。
• COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR
  申请人：HUMAN BIOMOLECULAR RESEARCH INSTITUTE

  公开号：US20160038641A1

  公开（公告）日：2016-02-11

  Compositions of small molecules, matrices, and isolated cells including methods of preparation, and methods for differentiation, transdifferentiation, and proliferation of animal cells into the osteoblast blast cell lineage were described. Examples of osteogenic materials that were administered to cells or co-cultured with cells are represented by compounds of Formula II, IV, and VI independently or preferably in combination with a matrix to afford bone cells. Small molecule-stimulated cells were also combined with a matrix, placed with a cellular adhesive or material carrier and implanted to a site in an animal for bone repair. Matrix pretreated with compounds of Formula II, IV, and VI were also used to cause cells to migrate to the matrix that is of use for therapeutic purposes.

  描述了由小分子、基质和孤立细胞组成的组合物，包括制备方法，以及动物细胞分化、转分化和增殖成骨母细胞谱系的方法。给细胞施加的或与细胞共培养的成骨材料的示例由独立或首选与基质组合的Formula II、IV和VI化合物代表。受小分子刺激的细胞还与基质结合，与细胞粘合剂或材料载体一起植入到动物体内的部位进行骨修复。预先用Formula II、IV和VI化合物处理的基质也被用于导致细胞迁移到用于治疗目的的基质上。
• Soluble beta amyloid precursor protein secretion promoters
  申请人：——

  公开号：US20030216398A1

  公开（公告）日：2003-11-20

  According to the present invention, there are provided compounds represented by formula (I): 1 [wherein R 1 and R 2 represent hydrogen atom, a lower alkyl group, etc.; ring A is an optionally substituted benzene ring, X is oxygen atom, etc.; and Y represents CH or N] or salts thereof, or prodrugs thereof, and use thereof as well as processes of manufacturing these compounds. The compounds of the present invention and the like possess a potent soluble beta amyloid precursor protein secretion promoting activity and suppress the functional disorders or apoptosis of cells, in particular neurons, mediated by the secreted soluble beta amyloid precursor proteins having a neurotrophic factor like property.

  根据本发明提供了以下公式（I）所代表的化合物：其中R1和R2代表氢原子、较低的烷基基团等；环A是一个可选择取代的苯环，X是氧原子等；Y代表CH或N；或其盐，或其前药，以及这些化合物的制造方法。本发明的化合物及类似化合物具有强大的可溶性β淀粉样前体蛋白分泌促进活性，并抑制细胞（特别是神经元）介导的具有类似神经营养因子特性的分泌可溶性β淀粉样前体蛋白引起的功能障碍或细胞凋亡。
• Radical cation salts induced domino reaction of anilines with enol ethers: Synthesis of 1,2,3,4-tetrahydroquinoline derivatives
  作者：Xiao Dong Jia、Yan Ren、Cong Dde Huo、Wen Juan Wang、Xiang Ning Chen、Qiong Fu、Xi Cun Wang

  DOI：10.1016/j.cclet.2010.12.038

  日期：2011.6

  A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA+ (5 mol%) was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthesized. Different from cyclic enol ethers, when acyclic enol ethers were used in the reaction, they serve as surrogates of acetaldehyde, producing a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines

  研究了催化量的TBPA +（5 mol％）诱导的苯胺与环状和无环烯醇醚的多米诺反应，并合成了一系列的2,4-二取代-1,2,3,4-四氢喹啉。与环状烯醇醚不同，当在反应中使用无环烯醇醚时，它们充当乙醛的替代物，产生一系列2-甲基-4-苯胺基1,2,3,4-四氢喹啉。提出了单一电子转移机制以合理化产物的形成。