2-chloro-6-methyl-3-nitrobenzonitrile | 74671-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-6-methyl-3-nitrobenzonitrile
• CAS: 74671-11-7
• 化学式: C₈H₅ClN₂O₂
• 分子量: 196.593
• InChiKey: DKXODNKVMAMTMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-6-methyl-3-nitrobenzonitrile 在 盐酸 、 硝酸 、 三氟乙酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 7-Chloro-6-methyl-2,3-dioxo-1,4-dihydroquinoxaline-5-carbonitrile
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2
• 作为产物：
  描述：

  2-氯-6-甲基苄腈 在 硝酸 、 三氟乙酸 作用下， 以1.61 g的产率得到2-chloro-6-methyl-3-nitrobenzonitrile
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2

文献信息

• N-Phenylpyrazole derivatives
  申请人：May & Baker Limited

  公开号：US04496390A1

  公开（公告）日：1985-01-29

  N-Phenylpyrazole derivatives of the formula: ##STR1## (wherein each of R.sup.5 and R.sup.6 represents a C.sub.1 -C.sub.4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R.sup.7, R.sup.8 and R.sup.9 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R.sup.5, R.sup.7, R.sup.8 and R.sup.9 each represents a hydrogen atom and R.sup.6 represents a trifluoromethoxy or trifluoromethyl radical, and R.sup.10 represents a cyano radical or substituted carbamoyl radical --CONHR.sup.11, wherein R.sup.11 represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1-(4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the preparation of the new compounds.

  N-苯基吡唑衍生物的化学式为：（其中R.sup.5和R.sup.6分别代表C.sub.1-C.sub.4烷基或烷氧基基团，三氟甲基，三氟甲氧基，硝基，氰基或一级氨基基团，或者氟，氯或溴原子，R.sup.7，R.sup.8和R.sup.9分别代表氢原子，C.sub.1-C.sub.4烷基或烷氧基基团，三氟甲基，三氟甲氧基，硝基，氰基或一级氨基基团，或者氟，氯或溴原子，或者R.sup.5，R.sup.7，R.sup.8和R.sup.9分别代表氢原子，R.sup.6代表三氟甲氧基或三氟甲基基团，R.sup.10代表氰基或取代的氨基甲酰基团--CONHR.sup.11，其中R.sup.11代表甲基或乙基基团）已被发现具有有用的除草特性。除了5-氨基-4-氰基-1-（2,4-二氯苯基）吡唑和5-氨基-4-氰基-1-（4-氯-2-甲基苯基）吡唑之外，所有这些N-苯基吡唑衍生物都是新化合物。描述了含有这些N-苯基吡唑衍生物的除草剂组合物以及制备新化合物的方法。
• N-phenylpyrazole derivatives
  申请人：MAY & BAKER LIMITED

  公开号：EP0034945A2

  公开（公告）日：1981-09-02

  N-Phenylpyrazole derivatives of the formula:- (wherein each of R5 and R6 represents a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R', R' and R9 represents a hydrogen atom, a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R5, R7, R' and R9 each represents a hydrogen atom and R6 represents a trifluoromethoxy or trifluoromethyl radical, and R10 represents a cyano radical or substituted carbamoyl radical -CONHR", wherein R" represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1- (4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the prepararation of the new compounds.

  式中的 N-苯基吡唑衍生物 (其中R5和R6各自代表C1-C4烷基或烷氧基、三氟甲基、三氟甲氧基、硝基、氰基或伯氨基或氟、氯或溴原子，R'、R'和R9各自代表氢原子、C1-C4烷基或烷氧基、三氟甲基、三氟甲氧基、硝基、氰基或伯氨基或氟、R5、R7、R'和 R9 各代表一个氢原子，R6 代表三氟甲氧基或三氟甲基基，R10 代表氰基或取代的氨基甲酰基 -CONHR"，其中 R "代表甲基或乙基）已被发现具有有用的除草特性。除 5-氨基-4-氰基-1-（2,4-二氯苯基）吡唑和 5-氨基-4-氰基-1-（4-氯-2-甲基苯基）吡唑外，所有这些 N-苯基吡唑衍生物都是新化合物。本文介绍了含有此类 N-苯基吡唑衍生物的除草组合物，以及制备这些新化合物的工艺。
• US4496390A
  申请人：——

  公开号：US4496390A

  公开（公告）日：1985-01-29
• Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists
  作者：Zhang-Lin Zhou、Sunil M Kher、Sui Xiong Cai、Edward R Whittemore、Stephen A Espitia、Jon E Hawkinson、Minhtam Tran、Richard M Woodward、Eckard Weber、John F.W Keana

  DOI：10.1016/s0968-0896(03)00059-2

  日期：2003.4

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.