1-[2-oxo-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-pyridinium bromide | 85019-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-[2-oxo-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-pyridinium bromide
• 英文别名: 2-Pyridin-1-ium-1-yl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone;bromide
• CAS: 85019-16-5
• 化学式: Br*C₁₇H₁₈NO
• 分子量: 332.24
• InChiKey: GVVCGAJVXBGFTI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯丙炔醛 、 1-[2-oxo-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-pyridinium bromide 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以83%的产率得到4-phenyl-6-(5,6,7,8-tetrahydronaphthalen-2-yl)-2H-pyran-2-one
  参考文献：
  名称：

  带有Ynals的Y环的N杂环碳环催化环空：直接获得α-Pyrones

  摘要：

  我们在此报告了N-杂环卡宾（NHC）催化的带有芳基的酰基化物环化，提供了制备4,6-二取代的α-吡喃酮的有效方法。该方法可提供高产率到高产率的各种α-吡喃酮，以及广泛的底物范围和良好的官能团耐受性。

  DOI：

  10.1002/asia.201800595
• 作为产物：
  描述：

  吡啶 、 2-溴-1-(5,6,7,8-四氢萘-2-基)乙酮 以 苯 为溶剂， 反应 0.5h， 以78%的产率得到1-[2-oxo-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-pyridinium bromide
  参考文献：
  名称：

  Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives

  摘要：

  The treatment of 2-bromo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (1) with pyridine, 2-methylpyridine or 4-methylpyridine afforded their corresponding pyridinum bromides 3a-c. The latter salts reacted with activated acetylene to give the corresponding indolizine derivatives 6a-c. Imidazo[1,2-a]pyridine 9a,b, quinoxaline 15, imidazo[1,2-b][1,2,4]triazole 18 and imidazo[1,2-a]benzimidazole 21 derivatives were prepared from 1 as a starting material. The investigation of the derivative influence on the carcinogen metabolizing enzymes and in the tumor initiation process revealed that 3a-c were strong inducers of epoxide hydrolase (mEH), and that 3a was an inducer of glutathione S-transferases (GSTs) and glutathione (GSH) and a potent scavenger of ROO center dot and OH center dot and inhibited the induced DNA damage, while 3b was a scavenger of ROO center dot and a moderate inhibitor of DNA damage. Additionally, 6a-c significantly induced quinine reductase (QR) activity, whereas 6b induced GSTs, and 6c elevated GSH content, while both of 6b and 6c scavenged OH center dot and inhibited the DNA damage. On the other hand, 9a possessed a moderate scavenging activity of ROO center dot and inhibitory effect on the induced DNA damage, while 18 was a strong inducer of QR activity, scavenger of OH center dot, and inhibitor of the DNA damage and 2 was a significant inhibitor of cytochrome P-450 1A (Cyp1A) and was an inducer of GSTs, and GSH, and a moderate inhibitor of the DNA damage. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.027

文献信息

• N-Heterocyclic Carbene-Catalyzed Annulation of Ylides with Ynals: Direct Access to α-Pyrones
  作者：Ming Lang、Qianfa Jia、Jian Wang

  DOI：10.1002/asia.201800595

  日期：2018.9.4

  We herein report an N‐Heterocyclic Carbene (NHC)‐catalyzed annulation of ylides with ynals that provides an efficient protocol to make 4,6‐disubstituted α‐pyrones. This method affords a variety of α‐pyrones in good to high yields as well as broad substrate scope and good functional group tolerance.

  我们在此报告了N-杂环卡宾（NHC）催化的带有芳基的酰基化物环化，提供了制备4,6-二取代的α-吡喃酮的有效方法。该方法可提供高产率到高产率的各种α-吡喃酮，以及广泛的底物范围和良好的官能团耐受性。
• Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives
  作者：Nehal A. Hamdy、Amira M. Gamal-Eldeen、Hatem A. Abdel-Aziz、Issa M.I. Fakhr

  DOI：10.1016/j.ejmech.2009.10.027

  日期：2010.2

  The treatment of 2-bromo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (1) with pyridine, 2-methylpyridine or 4-methylpyridine afforded their corresponding pyridinum bromides 3a-c. The latter salts reacted with activated acetylene to give the corresponding indolizine derivatives 6a-c. Imidazo[1,2-a]pyridine 9a,b, quinoxaline 15, imidazo[1,2-b][1,2,4]triazole 18 and imidazo[1,2-a]benzimidazole 21 derivatives were prepared from 1 as a starting material. The investigation of the derivative influence on the carcinogen metabolizing enzymes and in the tumor initiation process revealed that 3a-c were strong inducers of epoxide hydrolase (mEH), and that 3a was an inducer of glutathione S-transferases (GSTs) and glutathione (GSH) and a potent scavenger of ROO center dot and OH center dot and inhibited the induced DNA damage, while 3b was a scavenger of ROO center dot and a moderate inhibitor of DNA damage. Additionally, 6a-c significantly induced quinine reductase (QR) activity, whereas 6b induced GSTs, and 6c elevated GSH content, while both of 6b and 6c scavenged OH center dot and inhibited the DNA damage. On the other hand, 9a possessed a moderate scavenging activity of ROO center dot and inhibitory effect on the induced DNA damage, while 18 was a strong inducer of QR activity, scavenger of OH center dot, and inhibitor of the DNA damage and 2 was a significant inhibitor of cytochrome P-450 1A (Cyp1A) and was an inducer of GSTs, and GSH, and a moderate inhibitor of the DNA damage. (C) 2009 Elsevier Masson SAS. All rights reserved.