ethyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)acetate | 5100-58-3

• 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: ethyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)acetate
• 英文别名: ethyl (+/-)-1,2,3,4-tetrahydroquinoline-2-acetate；<1,2,3,4-Tetrahydro-2-chinolyl>-essigsaeure-ethylester；(1,2,3,4-tetrahydro-quinolin-2-yl)-acetic acid ethyl ester；Ethyl (1,2,3,4-tetrahydroquinolin-2-YL)acetate
• CAS: 5100-58-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: IYOKFCOGEPFIKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)acetate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 N-((S)-2-fluoro-3-hydroxy-3-methylbutyl)-2-((S)-1-((4-fluorophenyl)sulfonyl)-6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-1,2,3,4-tetrahydroquinolin-2-yl)acetamide
  参考文献：
  名称：

  Identification of bicyclic hexafluoroisopropyl alcohol sulfonamides as retinoic acid receptor-related orphan receptor gamma (RORγ/RORc) inverse agonists. Employing structure-based drug design to improve pregnane X receptor (PXR) selectivity

  摘要：

  We disclose the optimization of a high throughput screening hit to yield benzothiazine and tetrahydroquinoline sulfonamides as potent ROR gamma t inverse agonists. However, a majority of these compounds showed potent activity against pregnane X receptor (PXR) and modest activity against liver X receptor alpha (LXR alpha). Structure-based drug design (SBDD) led to the identification of benzothiazine and tetrahydro-quinoline sulfonamide analogs which completely dialed out LXR alpha activity and were less potent at PXR. Pharmacodynamic (PD) data for compound 35 in an IL-23 induced IL-17 mouse model is discussed along with the implications of a high Y-max in the PXR assay for long term preclinical pharmacokinetic (PK) studies. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.12.006
• 作为产物：
  描述：

  methyl (+/-)-2-(2-nitrophenyl)-4-pentenoate 在 sodium hydroxide 、 二甲基硫 、 铁粉 、 potassium carbonate 、 臭氧 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 12.25h， 生成 ethyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)acetate
  参考文献：
  名称：

  通过串联还原-迈克尔加成反应实现芳基稠合的氮杂环。

  摘要：

  DOI：

  10.1021/jo991899+

文献信息

• Synthesis of Substituted Azepino[3,4-<i>b</i>]indole-1,5-diones
  作者：Julien Perron、Benoît Joseph、Jean-Yves Mérour

  DOI：10.1002/ejoc.200400348

  日期：2004.11

  Cyclic β-amino esters 4, obtained from lactams, were condensed with indole-2-carbonyl chloride to afford the corresponding amides. Similarly, unusual conditions led to cyclisation at the 3-position of the indole moiety in the presence of pTSA and ethylene glycol to afford previously unknown pentacyclic derivatives 12 and 15. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  从内酰胺获得的环状 β-氨基酯 4 与吲哚-2-碳酰氯缩合得到相应的酰胺。同样，在 pTSA 和乙二醇存在下，不寻常的条件导致吲哚部分的 3 位环化，得到以前未知的五环衍生物 12 和 15。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国, 2004)
• US4040832A
  申请人：——

  公开号：US4040832A

  公开（公告）日：1977-08-09
• US4067871A
  申请人：——

  公开号：US4067871A

  公开（公告）日：1978-01-10
• US4067872A
  申请人：——

  公开号：US4067872A

  公开（公告）日：1978-01-10
• [EN] OXAZOLIDINONE COMPOUNDS CONTAINING RING-FUSED BICYCLIC RING, PREPARATION METHOD AND USE THEREOF<br/>[FR] COMPOSÉS OXAZOLIDINONE CONTENANT DEUX CYCLES FUSIONNÉS, PROCÉDÉ DE PRÉPARATION ASSOCIÉ ET UTILISATION ASSOCIÉE
  申请人：KPB BIOSCIENCES CO LTD

  公开号：WO2011097946A1

  公开（公告）日：2011-08-18

  Oxazolidinone compounds containing ring-fused bicyclic ring represented by the general formula (I), pharmaceutically acceptable salts and stereoisomers thereof are disclosed, wherein R1, R2, R3, R4, R5, R6, and -Y- are defined as in the description. Also disclosed are the preparation methods of such compounds, pharmaceutical compositions and pharmaceutical preparations containing the same and uses of the same in the manufacture of medicaments for treating and/or preventing infectious diseases, and in the treatment and/or prevention of infectious diseases.