1-benzyl-2-bromo-4,5-dicyanoimidazole | 134184-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-2-bromo-4,5-dicyanoimidazole
• 英文别名: N-benzyl-2-bromo-4,5-dicyanoimidazole；1-Benzyl-2-bromoimidazole-4,5-dicarbonitrile
• CAS: 134184-02-4
• 化学式: C₁₂H₇BrN₄
• 分子量: 287.118
• InChiKey: SDKKKUUWKVHCRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-bromo-4,5-dicyanoimidazole 生成 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(4,5-dicyano-1-benzyl-1H-imidazol-2-ylthio)methyl]-2H-1,2,3-triazole
  参考文献：
  名称：

  2-imidazol(in)e substituted aryl-1,2,3-triazole pesticides

  摘要：

  公式I的化合物及其盐，其中Ar、W、Z、A、R.sup.1-7、Y、m、p和n的含义如描述中所述，具有特别针对昆虫、螨虫和动物内寄生虫的杀虫活性。

  公开号：

  US05109012A1
• 作为产物：
  描述：

  氯化苄 、 2-溴-4,5-二氰基咪唑 在 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 以58%的产率得到1-benzyl-2-bromo-4,5-dicyanoimidazole
  参考文献：
  名称：

  Synthesis and properties of new derivatives of 4,5-dicyanoimidazole and 4,4',5,5'-tetracyano-2,2'-biimidazole

  摘要：

  The synthesis and properties of new derivatives of 4,5-dicyanoimidazole (1, HDcim) and 4,4',5,5'-tetracyano-2,2'-biimidazole (2, H2Tcbiim) are reported. Conditions for selective metalation at the 2-position of N-protected 4,5-dicyanoimidazoles are described. Various protecting groups were used. Oxidative coupling of N-protected 2-lithio-4,5-dicyanoimidazoles with cupric chloride gives new 1,1'-disubstituted derivatives of 4,4',5,5'-tetracyano-2,2'-biimidazole (13-15, R2Tcbiim where R = CH3, CH2OCH3, CH2Ph). Ullmann coupling of 1-methyl-2-bromo-4,5-dicyanoimidazole (6) gives (CH3)2Tcbiim (13). Deprotection of R2Tcbiim (when R = CH3 or CH2OCH3) gives H2Tcbiim (2). Several new routes to H2Tcbiim are now available. Reaction of H2Tcbiim with 1,n-dihaloalkanes (n = 2, 3, and 4) gives the corresponding 1,1'-alkyl-bridged derivatives 16-18 or (CH2)nTcbiim (n = 2, 3, and 4). (CH2)2Tcbiim (16) has also been synthesized via an intramolecular Ullmann coupling reaction of 19. The physical, structural, and electronic properties of these new cyanoimidazoles have been investigated by using UV-visible spectroscopy and cyclic voltammetry. Dicyanoimidazoles and tetracyanobiimidazoles are moderate to weak electron acceptors. (CH2)2Tcbiim (16) forms a 1:1 complex with tetrathiafulvalene (TTF). The donor (D)-acceptor (A) complex, [TTF][(CH2)2Tcbiim], forms as red needles from acetonitrile solution. X-ray crystallography of [TTF][(CH2)2Tcbiim] shows extended alternate or "mixed" stacking (...DADADA...). The photoluminescence spectrum of the complex shows an emission band centered at 660 nm with onset of emission at 530 nm.

  DOI：

  10.1021/ja00016a038

文献信息

• Azole pesticides
  申请人：AgrEvo UK Limited

  公开号：EP0412849A2

  公开（公告）日：1991-02-13

  Compounds of formula I and salts thereof, in which Ar is aryl; W is N and Z is CR⁵; or W is CR¹ and Z is N or CR⁵; A is S(O)m, -CH=CH-, O or NH; R¹ is hydrogen, optionally substituted alkyl, halogen or R²⁰S(O)q; R² and R³ are hydrogen, alkyl, alkenyl or alkynyl, each of which is optionally substituted, aryl, heterocyclyl, cyano, halogen, nitro, YR²⁰, S(O)₂NR⁸R⁹, CHO and functional derivatives thereof, NR⁸R⁹ or CYNR⁸R⁹; either (i) R⁴ and R⁷ which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted alkenyl, acyl or optionally substituted alkoxycarbonyl, and R⁶ is hydrogen, or (ii) R⁴ is as defined above and R⁶ and R⁷ form a bond or R⁷ is as defined above and R⁴ and R⁶ form a bond; R⁵ is hydrogen, alkyl, optionally substituted amino or halogen; R⁸ and R⁹ are the same or different and are hydrogen, optionally substituted alkyl, acyl or aryl, or together with the nitrogen to which they are attached, form a 5 to 7 membered ring which can contain other hetero atoms; R²⁰ is optionally substituted alkyl; Y is O or S; m is 0, 1 or 2; p is 0 or 1; n is 0, 1 or 2; and q is 0, 1 or 2, with the proviso that when W is CR¹ and Z is CR⁵ and n and p are both O, R⁴ and R⁷ are not alkyl, have pesticidal activity especially against insects, acarids and animal endoparasites.

  式 I 的化合物 及其盐类、 其中 Ar 为芳基 W 为 N，Z 为 CR⁵；或 W 为 CR¹，Z 为 N 或 CR⁵； A 是 S(O)m、-CH=CH-、O 或 NH； R¹ 是氢、任选取代的烷基、卤素或 R²⁰S(O)q； R² 和 R³ 是氢、烷基、烯基或炔基（其中每个都是任选取代的）、芳基、杂环基、氰基、卤素、硝基、YR²⁰、S(O)₂NR⁸R⁹、CHO 及其功能衍生物、NR⁸R⁹ 或 CYNR⁸R⁹； (i) R⁴ 和 R⁷ 可以相同或不同，它们是氢、任选取代的烷基、任选取代的烯基、酰基或任选取代的烷氧羰基，且 R⁶ 是氢，或 (ii) R⁴ 如上所定义，且 R⁶ 和 R⁷ 形成键，或 R⁷ 如上所定义，且 R⁴ 和 R⁶ 形成键； R⁵ 是氢、烷基、任选取代的氨基或卤素； R⁸ 和 R⁹ 既可以相同，也可以不同，它们是氢、任选取代的烷基、酰基或芳基，或者与它们所连接的氮一起形成一个 5 至 7 个成员的环，其中可以包含其他杂原子； R²⁰ 是任选取代的烷基； Y 是 O 或 S m 是 0、1 或 2 p为0或1 n 是 0、1 或 2；以及 q 为 0、1 或 2，但 W 为 CR¹，Z 为 CR⁵，n 和 p 均为 O 时，R⁴ 和 R⁷ 不是烷基、 具有杀虫活性，特别是对昆虫、害虫和动物内寄生虫。
• Intermolecular Interactions in Bromo-, Methyl-, and Cyanoimidazole Derivatives
  作者：Christopher J. Serpell、Paul D. Beer

  DOI：10.1021/cg400273p

  日期：2013.7.3

  Materials containing bistable N-H center dot center dot center dot N hydrogen bonds, such as imidazole crystals, show promise for applications in electronics. Herein, we examine the effect of imidazole functionalization upon structural parameters relating to proton transfer, molecular rotation, and order-disorder transitions. Three different substituents are studied: methyl-, bromo-, and cyano-, resulting in steric, electronic, and supramolecular modification of the imidazole core.
• US5109012A
  申请人：——

  公开号：US5109012A

  公开（公告）日：1992-04-28
• US5189053A
  申请人：——

  公开号：US5189053A

  公开（公告）日：1993-02-23