3-溴-8-甲基-6-硝基喹啉 | 210708-22-8

• 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
• 中文名称: 3-溴-8-甲基-6-硝基喹啉
• 英文名称: 3-bromo-8-methyl-6-nitroquinoline
• CAS: 210708-22-8
• 化学式: C₁₀H₇BrN₂O₂
• 分子量: 267.082
• InChiKey: SIHOVNCABQDJFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 储存条件：
  存放在室温、干燥且密封的环境中。

反应信息

• 作为反应物：
  描述：

  3-溴-8-甲基-6-硝基喹啉 在 盐酸 、 磷酸 、 铁粉 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 2-(3-bromo-8-methylquinolin-6-yloxy)-2-methylsulfanylacetic acid methyl ester
  参考文献：
  名称：

  Synthesis and fungicidal activity of quinolin-6-yloxyacetamides, a novel class of tubulin polymerization inhibitors

  摘要：

  A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula necator (grape powdery mildew). Their fungicidal activity is due to their ability to inhibit fungal tubulin polymerization, leading to microtubule destabilization. An efficient synthesis route has been worked out, which allows the diverse substitution of four identified key positions across the molecular scaffold.

  DOI：

  10.1016/j.bmc.2014.06.015
• 作为产物：
  描述：

  6-nitro-8-methylquinoline 在 溴 、 氯乙酸 作用下， 生成 3-溴-8-甲基-6-硝基喹啉
  参考文献：
  名称：

  Kermack; Wight, Journal of the Chemical Society, 1935, p. 1425

  摘要：

  DOI：

文献信息

• Core remodeling leads to long wavelength fluoro-coumarins
  作者：Siddharth S. Matikonda、Joseph Ivanic、Miguel Gomez、Gabrielle Hammersley、Martin J. Schnermann

  DOI：10.1039/d0sc02566f

  日期：——

  Fluoro-Coumarins are a novel class of far-red and near-infrared solvent sensitive dyes of exceptionally low molecular weight.

  Fluoro-Coumarins是一种新型的远红外和近红外溶剂敏感染料，分子量极低。
• 2,2,3-Tribromopropanal as a Versatile Reagent in the Skraup-Type Synthesis of 3-Bromoquinolin-6-ols
  作者：Clemens Lamberth、Fiona Kessabi、Renaud Beaudegnies、Laura Quaranta、Stephan Trah、Guillaume Berthon、Fredrik Cederbaum、Thomas Vettiger、CS Prasanna

  DOI：10.1055/s-0033-1340670

  日期：——

  2,2,3-Tribromopropanal, a reagent which almost became forgotten in the chemical literature after its first application in the 1950s, is used for the one-step transformation of diversely substituted 4-nitro- and 4-methoxyanilines into 3-bromo-6-nitroquinolines and 3-bromo-6-methoxyquinolines. These intermediates are then converted, in one further step, into 3-bromoquinolin-6-ols, which may carry additional substituents at positions 7 and 8.
• The Preparation of 3-Bromoquinoline Derivatives
  作者：Samuel W. Tinsley

  DOI：10.1021/ja01620a071

  日期：1955.8
• Synthesis of 1′,1‴-bis(heterocyclyl)biferrocene compounds
  作者：Chao-Min Liu、Yong-min Liang、Xiao-li Wu、Wei-min Liu、Yong-xiang Ma

  DOI：10.1016/s0022-328x(01)00895-6

  日期：2001.12

  A new method for preparing 1',l " ' -disubstituted heterocyclylbiferrocene derivatives via stepwise Stille coupling reaction of 1,1'-bis(tributylstannyl)ferrocene with heterocyclic bromides and subsequent Cu-catalyzed homocoupling reaction is established. (C) 2001 Elsevier Science B.V. All rights reserved.
• Conversion of tributylstannylferrocene to a variety of heteroaryl ferrocenes
  作者：Chao-Min Liu、Bao-Hua Chen、Wan-Yi Liu、Xiao-Li Wu、Yong-Xiang Ma

  DOI：10.1016/s0022-328x(99)00733-0

  日期：2000.4

  Tributylstannylferrocene (Fc-SnBu3) was converted to a variety of heteroaryl ferrocenes, such as 2-thiophenyl, 3-thiophenyl, 3-pyridyl, 3-quinolyl, 4-oxazolyl and 4-isoxazolyl ferrocene, by using Pd-catalyzed reactions. The Stille-coupling catalyst (PdCl2-PPh3) promotes the reaction between Fc-SnBu3 and electron-deficient heterocyclic bromides, while a modified catalyst (Pd-Ph3P-CuO) proves to be the choice for the coupling of Fc-SnBu3 with electron-rich heterocyclic bromides. (C) 2000 Elsevier Science S.A. All rights reserved.