N-氰基-N’-甲基-乙亚胺基胺 | 56563-12-3

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-氰基-N’-甲基-乙亚胺基胺
• 中文别名: N-氰基-N'-甲基-乙亚胺基胺
• 英文名称: N-methyl-N'-cyanoacetamidine
• 英文别名: N-Cyano-N'-methyl-ethanimidamide；N-cyano-N'-methylethanimidamide
• CAS: 56563-12-3
• 化学式: C₄H₇N₃
• mdl: MFCD04972463
• 分子量: 97.1197
• InChiKey: HGUZMABFJZHYJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

化学性质 

本品为白色粉末，m.p.97.2～100.4℃，不溶于水。

用途 

N-氰基-N′-甲基乙脒是杀虫剂啶虫脒的中间体。

生产方法 

其制备方法是以乙腈和甲醇为原料，通入干燥氯化氢，得到甲基乙酰亚胺酯，然后与氰胺反应生成N-氰基甲基乙酰亚胺酯，最后与甲胺反应生成N-氰基-N′-甲基乙脒。

反应信息

• 作为反应物：
  描述：

  N-氰基-N’-甲基-乙亚胺基胺 、 甲基5-(氯甲基)烟酸酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  一种啶虫脒半抗原、完全抗原及其合成与应用

  摘要：

  本发明提供一种啶虫脒半抗原、完全抗原的合成与应用，包括一种啶虫脒半抗原。本发明涉及一种啶虫脒半抗原，该啶虫脒半抗原是以氯甲基烟酸甲酯为原料所合成的一种新的啶虫脒半抗原，该啶虫脒半抗原保留了啶虫脒的主要结构；本发明还涉及该啶虫脒半抗原的合成方法，该合成方法保留了啶虫脒的主要结构，相比于现有技术能够节约啶虫脒半抗原的合成成本，提高啶虫脒半抗原的合成效率。

  公开号：

  CN113943248B
• 作为产物：
  描述：

  N'-cyano-N-(2-cyanoethyl)-N-methylethanimidamide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 N-氰基-N’-甲基-乙亚胺基胺
  参考文献：
  名称：

  Studien über dieThorpe-Ziegler-Reaktion Eine neue Synthese des Pyrimidinteils von Thiamin

  摘要：

  AbstractThorpe‐Ziegler cyclization of N′‐cyano‐N‐(2‐cyanoethyl)‐acetamidine (5a) yields 4‐amino‐2‐methyl‐1,6‐dihydro‐5‐pyrimidinecarbonitrile (8a). The acetamidine 5a is accessible either from the N‐cyanoimidate 1 and β‐aminopropionitrile (3a) or the N‐cyanoamidine 2 and acrylonitrile (4). The dihydropyrimidine 8a is easily converted to 4‐amino‐2‐methyl‐5‐pyrimidine‐carbonitrile (13) by dehydrogenation or to 4‐amino‐5‐aminomethyl‐2‐methylpyrimidine (15) by hydrogenation‐dehydrogenation. Both products are important intermediates in the synthesis of thiamine.

  DOI：

  10.1002/hlca.19750580429

文献信息

• Pyridine compounds which have useful insecticidal utility
  申请人：Nippon Soda Co., Ltd

  公开号：US05304566A1

  公开（公告）日：1994-04-19

  The present invention relates to a compound having the formula below which has an excellent inseciticidal activity: ##STR1## wherein R.sub.1 represents an optionally substituted 5-6 membered aromatic hetero ring containing nitrogen atom, except a non-substituted 2-pyridyl; x represents an optionally substituted C.sub.1-3 alkylene R.sub.2 represents a hydrogen, a carbamoyl, a mono or di C.sub.1-5 alkyl carbamoyl, a thiocarbamoyl, a mono or di C.sub.1-5 alkylthiocarbamoyl, a sulfamoyl, a mono or di C.sub.1-5 alkylsulfamoyl, an optionally substituted C.sub.1-5 alkyl, an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.sub.2-5 alkynyl, an optionally substituted C.sub.3-8 cycloalkyl, an optionally substituted C.sub.3-8 cycloalkenyl, an optionally substituted aryl or --Y--R.sub.5 ; Y represents O, S(O).sub.n, CO, CS or CO.sub.2 ; n represents 0, 1 or 2; R.sub.5 represents a hydrogen, an optionally substituted C.sub.1-5 alkyl, an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.sub.2-5 alkynyl, an optionally substituted C.sub.3-8 cycloalkyl, an optionally substituted C.sub.3-8 cycloalkenyl or an optionally substituted aryl; R.sub.3 represents a hydrogen, an optionally substituted C.sub.1-5 alkyl, an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.sub.2-5 alkynyl, an optionally substituted C.sub.3-8 cycloalkyl or an optionally substituted C.sub.3-8 cycloalkenyl; R.sub.4 represents a cyano or a nitro; and Z represents CH or N; or its salt.

  本发明涉及一种具有以下式的化合物，具有优良的杀虫活性：##STR1##其中R.sub.1表示一个可选择取代的含氮原子的5-6成员芳香杂环，但不包括非取代的2-吡啶基；x表示一个可选择取代的C.sub.1-3烷基；R.sub.2表示氢、羰基、一元或二元C.sub.1-5烷基羰基、硫代羰基、一元或二元C.sub.1-5烷基硫代羰基、磺胺基、一元或二元C.sub.1-5烷基磺胺基、可选择取代的C.sub.1-5烷基、可选择取代的C.sub.2-5烯基、可选择取代的C.sub.2-5炔基、可选择取代的C.sub.3-8环烷基、可选择取代的C.sub.3-8环烯基、可选择取代的芳基或--Y--R.sub.5；Y表示O、S(O).sub.n、CO、CS或CO.sub.2；n表示0、1或2；R.sub.5表示氢、可选择取代的C.sub.1-5烷基、可选择取代的C.sub.2-5烯基、可选择取代的C.sub.2-5炔基、可选择取代的C.sub.3-8环烷基、可选择取代的C.sub.3-8环烯基或可选择取代的芳基；R.sub.3表示氢、可选择取代的C.sub.1-5烷基、可选择取代的C.sub.2-5烯基、可选择取代的C.sub.2-5炔基、可选择取代的C.sub.3-8环烷基或可选择取代的C.sub.3-8环烯基；R.sub.4表示氰基或硝基；Z表示CH或N；或其盐。
• [6-chloro-3-pyridylmethyl-3H] neonicotinoids as high-affinity radioligands for the nicotinic acetylcholine receptor: Preparation using NaB3H4 and LiB3H4
  作者：Bachir Latli、Chit Than、Hiromi Morimoto、Philip G. Williams、John E. Casida

  DOI：10.1002/(sici)1099-1344(199611)38:11<971::aid-jlcr923>3.0.co;2-u

  日期：1996.11
• Water bridges are essential to neonicotinoids: Insights from synthesis, bioassay and molecular modelling studies
  作者：Chengchun Zhu、Guanglong Li、Keya Xiao、Xusheng Shao、Jiagao Cheng、Zhong Li

  DOI：10.1016/j.cclet.2018.05.013

  日期：2019.1

  Water-bridged H-bonds have been observed in many cases of ligand-receptor recognitions. To explore the roles of water bridges in the binding of neonicotinoids with receptors, twenty-four neonicotinoid compounds with nine fragments, including 1H-1,2,3-triazole, CN, COOMe, CONHNH2, CONHMe, NO2, NH2, NHCOMe and NHCSNH2 were synthesized and evaluated, of which, compounds with cyano group showed the best activities against Aphis craccivora. Accordingly, the cyano group is the optimal fragment mimicking the water bridge. Two cyano-substituted cis-nitromethylene compounds display good insecticidal activities, whereas the LC50 values are lower than those of their corresponding prototypes. Docking study showed that the cyano group acts only as H-bond acceptor, while the water bridge can act as both donor and acceptor. It revealed that the water bridge might be stable in the active site and was not suitable to be replaced by other groups. The findings illustrated that the water bridge is necessary for high insecticidal activities of neonicotinoids, which should be also helpful in better understanding the binding mode of neonicotinoids. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.