4,5-二氰基-1-乙基-1H-咪唑 | 133123-67-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4,5-二氰基-1-乙基-1H-咪唑
• 英文名称: 1-ethyl-4,5-dicyanoimidazole
• 英文别名: 4,5-Dicyano-1-ethylimidazole；1-Ethyl-1H-imidazole-4,5-dicarbonitrile；1-ethylimidazole-4,5-dicarbonitrile
• CAS: 133123-67-8
• 化学式: C₇H₆N₄
• 分子量: 146.151
• InChiKey: RAFSTXGDSLCINC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  4,5-二氰基-1-乙基-1H-咪唑 、 三氟甲烷磺酸甲酯 以 甲苯 为溶剂， 反应 72.0h， 以67%的产率得到1-ethyl-3-methyl-4,5-dicyanoimidazolium triflate
  参考文献：
  名称：

  Strategies toward the design of energetic ionic liquids: nitro- and nitrile-substituted N,N′-dialkylimidazolium salts

  摘要：

  合成了12种新型1,3-二烷基咪唑鎓盐，其阳离子杂环上直接附加了强吸电子硝基和氰基功能团；通过DSC、TGA和单晶X射线衍射确定了取代基对所得离子液体形成和热性质的影响，结果表明吸电子硝基取代基可以成功附加，并且对熔融行为的影响与相应的甲基取代相似。由于二硝基取代的咪唑对N-烷基化或质子化的抵抗力，未能成功合成二硝基或三硝基取代的1,3-二烷基咪唑鎓阳离子，而1-烷基-4,5-二氰基咪唑成功进行了烷基化，得到了1,3-二烷基-4,5-二氰基咪唑鎓盐。五种晶体结构（每种阳离子类型各一种）显示，在固态下，NO2基团对晶体堆积的影响不大，仅限于空间贡献。

  DOI：

  10.1039/b509260d
• 作为产物：
  描述：

  原甲酸三乙酯 、 二氨基马来腈 以97%的产率得到4,5-二氰基-1-乙基-1H-咪唑
  参考文献：
  名称：

  1-Alkylation of 4,5-Dicyanoimidazole by Ortho Esters

  摘要：

  再次检验了邻醇酯与二氨基美克腈（1）或4,5-二氰基咪唑（3a）的反应后发现，可以通过一步法在不添加任何额外试剂的情况下高产率获得1-烷基-4,5-二氰基咪唑（4a-f）。这一简单的操作经济上与其他已知方法具有竞争力。先前报道的类似反应的几个产物已证明是二氨基美克腈的咪唑酯，2b和7。

  DOI：

  10.1055/s-1991-26384

文献信息

• HIV replication inhibiting pyrimidines
  申请人：Janssen Pharmaceutica NV

  公开号：US10370340B2

  公开（公告）日：2019-08-06

  This invention concerns HIV replication inhibitors of formula the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and the stereochemically isomeric forms thereof, wherein the ring containing -a1=a2-a3=a4- and -b1=b2-b3=b4- represents phenyl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl; n is 0 to 5; m is 1 to 4; R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyl; C1-6alkyloxycarbonyl; substituted C1-6alkyl, C1-6alkylcarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonyloxy; substituted C1-6alkyloxyC1-6alkylcarbonyl; R2 is hydroxy, halo, optionally substituted C1-6alkyl, C3-7cycloalkyl, optionally substituted C2-6alkenyl, optionally substituted C2-6alkynyl, C1-6alkyloxy, C1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C1-6alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, —S(═O)pR6, —NH—S(═O)pR6, —C(═O)R6, —NHC(═O)H, —C(═O)NHNH2, —NHC(═O)R6, —C(═NH)R6 or a 5-membered heterocycle; X1 is —NR5—, —NH—NH—, —N═N—, —O—, —C(═O)—, C1-4alkanediyl, —CHOH—, —S—, —S(═O)p—, —X2—C1-4alkanediyl- or —C1-4alkanediyl-X2—; R3 is NHR13; NR13R14; —C(═O)—NHR13; —C(═O)—NR13R14; —C(═O)—R15; —CH═N—NH—C(═O)—R16; substituted C1-6alkyl; optionally substituted C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl; substituted C2-6alkynyl; C1-6alkyl substituted with hydroxy and a second substituent; —C(═N—O—R8)—C1-4alkyl; R7; or —X3—R7; R4 is halo, hydroxy, C1-6alkyl, C3-7cycloalkyl, C1-6alkyloxy, cyano, nitro, polyhaloC1-6alkyl, polyhaloC1-6alkyloxy, aminocarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonyl, formyl, amino, mono- or di(C1-4alkyl)amino; their use as a medicine, their processes for preparation and pharmaceutical compositions comprising them.

  本发明涉及式中的艾滋病毒复制抑制剂 的N-氧化物、药学上可接受的加成盐、季胺及其立体异构体形式，其中含有-a1=a2-a3=a4-和-b1=b2-b3=b4-的环代表苯基、吡啶基、嘧啶基、吡嗪基、哒嗪基；n 为 0 至 5；m 为 1 至 4；R1 为氢；芳基；甲酰基；C1-6烷基羰基；C1-6烷基；C1-6烷氧基羰基；取代的 C1-6烷基、C1-6烷基羰基、C1-6烷氧基羰基、C1-6烷基羰基氧基、C1-6烷基羧基取代的 C1-6 烷氧基 C1-6 烷基羰基；R2 是羟基、卤代、任选取代的 C1-6 烷基、C3-7 环烷基、任选取代的 C2-6 烯基、任选取代的 C2-6 烷炔基、C1-6 烷氧基、C1-6 烷氧羰基、羧基、氰基、硝基、氨基、单或二(C1-6烷基)氨基、多卤代甲基、多卤代甲基氧基、多卤代甲硫基、-S(═O)pR6、-NH-S(═O)pR6、-C(═O)R6、-NHC(═O)H、-C(═O)NHNH2、-NHC(═O)R6、-C(═NH)R6 或 5 元杂环；X1 是-NR5-、-NH-NH-、-N═N-、-O-、-C(═O)-、C1-4烷二基、-CHOH-、-S-、-S(═O)p-、-X2-C1-4烷二基-或-C1-4烷二基-X2-； R3 是 NHR13； NR13R14；-C(═O)-NHR13；-C(═O)-NR13R14；-C(═O)-R15；-CH═N-NH-C(═O)-R16；取代的 C1-6 烷基；任选取代的 C1-6 烷氧基 C1-6 烷基；取代的 C2-6 烯基；取代的 C2-6 烷炔基；被羟基和第二个取代基取代的 C1-6 烷基；-C(═N-O-R8)-C1-4烷基；R7；或-X3-R7；R4是卤代、羟基、C1-6烷基、C3-7环烷基、C1-6烷氧基、氰基、硝基、多卤代C1-6烷基、多卤代C1-6烷氧基、氨基羰基、C1-6烷氧基羰基、C1-6烷基羰基、甲酰基、氨基、单-或二(C1-4烷基)氨基；它们作为药物的用途、制备工艺和由它们组成的药物组合物。
• HIV INHIBITING PYRIMIDINES DERIVATIVES
  申请人：Janssen Pharmaceutica NV

  公开号：EP2298761B1

  公开（公告）日：2020-03-25
• Pyrimidine derivatives for the prevention of hiv infection
  申请人：Heeres Jan

  公开号：US20070021449A1

  公开（公告）日：2007-01-25

  This invention concerns the use of a compound for the manufacture of a medicament for the prevention of HIV infection via sexual intercourse and related intimate contact between partners, wherein the compound is a compound of formula (I) a N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine and a stereochemically isomeric form thereof, wherein the ring containing -a 1 =a 2 -a 3 =a 4 - and -b 1 =b 2 -b 3 =b 4 - represents phenyl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl; and pharmaceutical compositions comprising them.
• PYRIMIDINE DERIVATIVES FOR THE PREVENTION OF HIV INFECTION
  申请人：HEERES Jan

  公开号：US20100034810A1

  公开（公告）日：2010-02-11

  This invention concerns the use of a compound for the manufacture of a medicament for the prevention of HIV infection via sexual intercourse and related intimate contact between partners, wherein the compound is a compound of formula a N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine and a stereochemically isomeric form thereof, wherein the ring containing -a 1 =a 2 -a 3 =a 4 - and -b 1 =b 2 -b 3 =b 4 - represents phenyl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl; n is 0 to 5; m is 1 to 4; R 1 is hydrogen; aryl; formyl; C 1-6 alkylcarbonyl; C 1-6 alkyl; C 1-6 alkyloxycarbonyl; substituted C 1-6 alkyl, C 1-6 alkylcarbonyl, C 1-6 alkyloxycarbonyl, C 1-6 alkylcarbonyloxy; substituted C 1-6 alkyloxyC 1-6 alkylcarbonyl; R 2 is hydroxy, halo, optionally substituted C 1-6 alkyl, C 3-7 cycloalkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, C 1-6 alkyloxy, C 1-6 alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C 1-6 alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, —S(═O) p R 6 , —NH—S(═O) p R 6 , —C(═O)R 6 , —NHC(═O)H, —C(═O)NHNH 2 , —NHC(═O)R 6 , —C(═NH)R 6 or a 5-membered heterocycle; X 1 is —NR 5 —, —NH—NH—, —N═N—, —O—, —C(═O)—, C 1-4 alkanediyl, —CHOH—, —S—, —S(═O) p —, —X 2 —C 1-4 alkanediyl- or —C 1-4 alkanediyl-X 2 —; R 3 is NHR 13 ; NR 13 R 14 ; —C(═O)—NHR 13 ; —C(═O)—NR 13 R 14 ; —C(═O)—R 15 ; —CH═N—NH—C(═O)—R 16 ; substituted C 1-6 alkyl; optionally substituted C 1-6 alkyloxyC 1-6 alkyl; substituted C 2-6 alkenyl; substituted C 2-6 alkynyl; C 1-6 alkyl substituted with hydroxy and a second substituent; —C(═N—O—R 8 )—C 1-4 alkyl; R 7 ; or —X 3 —R 7 ; R 4 is halo, hydroxy, C 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkyloxy, cyano, nitro, polyhaloC 1-6 alkyl, polyhaloC 1-6 alkyloxy, aminocarbonyl, C 1-6 alkyloxycarbonyl, C 1-6 alkylcarbonyl, formyl, amino, mono- or di(C 1-4 alkyl)amino; and pharmaceutical compositions comprising them.
• US20140343006A1
  申请人：——

  公开号：US20140343006A1

  公开（公告）日：2014-11-20