2-Chloro-3-methyl-7-trifluoromethylquinoxaline | 166402-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-Chloro-3-methyl-7-trifluoromethylquinoxaline
• 英文别名: 3-Chloro-6-(trifluoromethyl)-2-methylquinoxaline；3-chloro-2-methyl-6-(trifluoromethyl)quinoxaline
• CAS: 166402-14-8
• 化学式: C₁₀H₆ClF₃N₂
• 分子量: 246.619
• InChiKey: PRFPCGUDBQRSIX-UHFFFAOYSA-N

物化性质

• 沸点：
  271.2±35.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Chloro-3-methyl-7-trifluoromethylquinoxaline 在 palladium on activated charcoal 盐酸 、 selenium(IV) oxide 、 水 、 氢气 、 双氧水 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 15.0~85.0 ℃ 、303.98 kPa 条件下， 反应 6.83h， 生成 6-(三氟甲基)喹喔啉-2-甲醛
  参考文献：
  名称：

  Quinoxaline chemistry. Part 15. 4-[2-Quinoxalylmethylenimino]-benzoylglutamates and -benzoates, 4-[2-quinoxalylmethyl-N-methylamino]-benzoylglutamates as analogues of classical antifolate agents. Synthesis, elucidation of structures and in vitro evaluation of antifolate and anticancer activities

  摘要：

  We report on an extension of our previous discovery of in vitro anticancer activity of trifluoromethylquinoxalines as analogues of classical and non-classical antifolic methotrexate and trimetrexate. In this case a small number of Schiff bases were obtained from the reaction of 2-bromethyl-3-R-6(7)trifluoromethylquinoxaline and ethyl p-aminobenzoylglutamate, ethyl p-aminobenzoate, p-toluidine instead of the expected 4-[2-quinoxalyl]methyl-N-methylanilino derivatives, which in turn formed with N-methylanilino derivatives. The reaction mechanism has been put forward. Structure elucidation of both Schiff bases and N-methylanilino analogues was achieved by a combination of 1H and 13C NMR spectra and hetcor experiments. Compounds 3a, 3b, 3c, 8, 11, 12, 13, Ie were tested in antifolic enzyme assay [Lactobacillus casei (LcTS), Leishmania major (LmTs), human Thymidylate synthase (hTs), human TS, human dihydrofolate reductase (hDHFR)] while compounds 3a, 3b, 3c were tested for anticancer activity. These results seem to indicate that the Schiff bases are somewhat active either as anticancer or as folate inhibitors, while compound Ie was selectively active against hDHFR with an inhibition constant (Ki) of 200 nM with a specificity of about 1000-folds with respect to hTS.

  DOI：

  10.1016/s0014-827x(02)00005-8
• 作为产物：
  描述：

  N-<(2-Nitro-4-trifluoromethyl)phenyl>alanine 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 双氧水 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 15.0~100.0 ℃ 、303.98 kPa 条件下， 反应 3.33h， 生成 2-Chloro-3-methyl-7-trifluoromethylquinoxaline
  参考文献：
  名称：

  Loriga; Fiore; Sanna, Il Farmaco, 1995, vol. 50, # 5, p. 289 - 301

  摘要：

  DOI：

文献信息

• SUBSTITUTED QUINOXALINE DERIVATIVES AS PEST CONTROL AGENT
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20160227779A1

  公开（公告）日：2016-08-11

  The invention relates to novel compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Y 1 and Y 2 have the meanings given above, to a plurality of processes and intermediates for their preparation and to their use as acaricides and/or insecticides for controlling animal pests. The compounds of the formula (I) are also suitable as nematicides for plant-damaging pests and/or anthelminthics for endoparasites in humans and animals.

  这项发明涉及公式（I）的新化合物， 其中R1、R2、R3、R4、R5、R6、Y1和Y2具有上述给定的含义， 以及用于它们的制备的多种过程和中间体，以及它们作为杀螨剂和/或杀虫剂用于控制动物害虫。公式（I）的化合物也适用于作为杀线虫剂用于植物有害害虫和/或作为人类和动物内寄生虫的驱虫剂。
• [EN] (1,2,4)TRIAZOLO[4,3-A]QUINOXALINE DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASES<br/>[FR] DÉRIVÉS DE (1,2,4)TRIAZOLO[4,3-A]QUINOXALINE UTILISÉS COMME INHIBITEURS DES PHOSPHODIESTÉRASES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012104293A1

  公开（公告）日：2012-08-09

  The invention relates to (1,2,4)triazolo[4,3-a]quinoxaline derivatives of Formula (I) which are inhibitors of phosphodiesterase 2 and/or 10, useful in treating central nervous system diseases.

  该发明涉及式(I)的(1,2,4)三唑并[4,3-a]喹喔啉衍生物，它们是磷酸二酯酶2和/或10的抑制剂，可用于治疗中枢神经系统疾病。
• (1,2,4)TRIAZOLO[4,3-A]QUINOXALINE DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASES
  申请人：Lankau Hans-Joachim

  公开号：US20120302564A1

  公开（公告）日：2012-11-29

  The invention relates to (1,2,4)triazolo[4,3-a]quinoxaline derivatives which are inhibitors of phosphodiesterase 2 and/or 10, useful in treating central nervous system diseases.

  这项发明涉及（1,2,4）三唑并[4,3-a]喹啉衍生物，它们是磷酸二酯酶2和/或10的抑制剂，可用于治疗中枢神经系统疾病。
• Loriga; Fiore; Sanna, Il Farmaco, 1996, vol. 51, # 8-9, p. 559 - 568
  作者：Loriga、Fiore、Sanna、Paglietti

  DOI：——

  日期：——
• SUBSTITUIERTE CHINOXALIN-DERIVATE ALS SCHÄDLINGSBEKÄMPFUNGSMITTEL
  申请人：Bayer CropScience Aktiengesellschaft

  公开号：EP3060557A1

  公开（公告）日：2016-08-31