1,2,3,4-tetrahydro-6-methoxy-1-methylquinoline | 74492-61-8

• 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: 1,2,3,4-tetrahydro-6-methoxy-1-methylquinoline
• 英文别名: 1-methyl-6-methoxy-1,2,3,4-tetrahydroquinoline；6-methoxy-1-methyl-1,2,3,4-tetrahydroquinoline；6-methoxykairoline；6-methoxy-1-methyl-1,2,3,4-tetrahydro-quinoline；6-Methoxy-1-methyl-1,2,3,4-tetrahydro-chinolin；6-methoxy-1-methyl-3,4-dihydro-2H-quinoline
• CAS: 74492-61-8
• 化学式: C₁₁H₁₅NO
• mdl: MFCD13179572
• 分子量: 177.246
• InChiKey: ZCCIIGUSMFBKAN-UHFFFAOYSA-N

物化性质

• 沸点：
  150-151 °C(Press: 10 Torr)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-6-methoxy-1-methylquinoline 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甘油 、 乙腈 为溶剂， 反应 2.0h， 生成 8-sec-butenyl-6-methoxy-1-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Katayama, Hajime; Tachikawa, Yoshio; Takatsu, Noriyuki, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 7, p. 2220 - 2233

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲氧基喹啉 在 盐酸 、 甲醇 、 tin 作用下， 生成 1,2,3,4-tetrahydro-6-methoxy-1-methylquinoline
  参考文献：
  名称：

  Skraup, Monatshefte fur Chemie, 1885, vol. 6, p. 767

  摘要：

  DOI：

文献信息

• Novel Carbamates as Orally Active Acetylcholinesterase Inhibitors Found to Improve Scopolamine-Induced Cognition Impairment: Pharmacophore-Based Virtual Screening, Synthesis, and Pharmacology
  作者：Shailendra S. Chaudhaery、Kuldeep K. Roy、Neeraj Shakya、Gunjan Saxena、Shreesh Raj Sammi、Aamir Nazir、Chandishwar Nath、Anil K. Saxena

  DOI：10.1021/jm100573q

  日期：2010.9.9

  library led to the identification of novel carbamates as potent AChE inhibitors. The synthesis and pharmacological evaluation of nine carbamates against three diverse assay systems, namely (i) in vitro Ellman method, (ii) in vivo passive avoidance test, and (iii) aldicarb-sensitivity assay, led to the discovery of orally active novel AChE inhibitors which improved scopolamine-induce cognition impairment

  据报道，系统的虚拟筛选（VS）实验包括3D药效团的开发，虚拟文库的筛选，合成和药理学。使用HypoGen在一组24种氨基甲酸酯作为AChE抑制剂的训练集上开发了具有一个H键供体和三个疏水特征的预测药效团模型（相关性= 0.955）。该模型在40个氨基甲酸酯的测试集中进行了验证（相关系数= 0.844）。虚拟库基于药效团的VS导致鉴定出新型氨基甲酸酯作为有效的AChE抑制剂。九种氨基甲酸酯的合成和药理学评估，针对三种不同的测定系统，即（i）体外Ellman方法，（ii）体内被动回避测试和（iii）涕灭威敏感性测定，导致发现了口服活性新型AChE抑制剂，该抑制剂可改善东pol碱诱导的瑞士雄性小鼠认知障碍。最后，两种新颖的先导化合物选择85和86作为候选分子用于进一步优化。
• [EN] PYRIMIDINE COMPOUNDS AND PYRIMIDO INDOLE COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS DE PYRIMIDINE ET COMPOSÉS DE PYRIMIDO INDOLE ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：UNIV HOLY GHOST DUQUESNE

  公开号：WO2016022890A1

  公开（公告）日：2016-02-11

  The present invention discloses substituted pyrimidine and pyrimido indole compounds and optionally pharmaceutically acceptable salts, hydrates or solvates thereof. A method of treating a patient having cancer or a disease comprising administering to a patient an effective amount of the compound or pharmaceutically acceptable salt, hydrate, or solvate thereof.

  本发明公开了取代嘧啶和嘧啶并吲哚化合物以及可选择的药用盐、水合物或溶剂化合物。一种治疗患有癌症或疾病的患者的方法包括向患者投予化合物或其药用盐、水合物或溶剂化合物的有效量。
• Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N‐methylation
  作者：Chao‐Zheng Zhou、Yu‐Rou Zhao、Fang‐Fang Tan、Yan‐Jun Guo、Yang Li

  DOI：10.1002/cctc.202101099

  日期：2021.11.22

  Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various

  木质纤维素生物质是自然界中最丰富的可再生资源之一。在此，我们开发了利用木质纤维素生物质中的可再生甲酸作为氢源和碳源，在温和条件下高效地对各种喹啉及其衍生物、各种吲哚进行选择性加氢和进一步 N-甲基化。还开发了各种苯胺的 N-甲基化。机理研究表明氢化通过转移氢化途径发生。
• Therapeutic diphenyl ether ligands
  申请人：Fliri J. Anton

  公开号：US20060058361A1

  公开（公告）日：2006-03-16

  This invention is directed to compounds of formula Ia, Ib or Ic and to pharmaceutical compositions thereof: or a prodrug thereof and a pharmaceutically acceptable carrier, wherein the R groups are defined in the specification; and, in which the dashed line represents an optional double bond. The invention is also directed to methods of treating, diagnosing, and preventing disorders of the central nervous system that are associated with 5HT receptors, including obesity, attention deficit disorder, migraine, depression, epilepsy, anxiety, Alzheimer's disease, withdrawal from drug abuse, pain, schizophrenia, stress-related disorders, panic disorder, sleep disorders, phobias, obsessive compulsive disorder, post-traumatic-stress syndrome, immune system depression, stress-induced gastrointestinal dysfunction, stress-induced cardiovascular dysfunction, and sexual dysfunction.

  该发明涉及式Ia、Ib或Ic的化合物，以及其药物组成物：或其前药和药用可接受载体，其中R基在规范中定义；以及虚线代表可选的双键。该发明还涉及治疗、诊断和预防与5HT受体相关的中枢神经系统疾病的方法，包括肥胖、注意缺陷障碍、偏头痛、抑郁症、癫痫、焦虑、阿尔茨海默病、戒毒、疼痛、精神分裂症、应激相关疾病、恐慌症、睡眠障碍、恐惧症、强迫症、创伤后应激综合征、免疫系统抑郁、应激引起的胃肠功能障碍、应激引起的心血管功能障碍和性功能障碍。
• Reductive <i>N</i>-methylation of quinolines with paraformaldehyde and H₂ for sustainable synthesis of <i>N</i>-methyl tetrahydroquinolines
  作者：Hongli Wang、Yongji Huang、Qi Jiang、Xingchao Dai、Feng Shi

  DOI：10.1039/c8cc10309g

  日期：——

  One-pot reductive N-methylation of quinolines with paraformaldehyde and H₂ over Pd/C catalyst was developed for the synthesis of N-methyl-1,2,3,4-tetrahydroquinolines.

  使用Pd/C催化剂，通过一锅法将喹啉与多聚甲醛和H₂还原N-甲基化，合成N-甲基-1,2,3,4-四氢喹啉。