(3,5-dimethylphenyl)cyanamide | 56979-86-3

• 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: (3,5-dimethylphenyl)cyanamide
• 英文别名: 3,5-Dimethyl-phenyl-cyanamide
• CAS: 56979-86-3
• 化学式: C₉H₁₀N₂
• 分子量: 146.192
• InChiKey: ZFQMSPFLYBUSLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3,5-dimethylphenyl)cyanamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-(3,5-Dimethylphenyl)-1-methyl-2-naphthalen-1-ylguanidine
  参考文献：
  名称：

  Synthesis and in vitro evaluation of N,N′-diphenyl and N-naphthyl-N′-phenylguanidines as N-methyl-d-aspartate receptor ion-channel ligands

  摘要：

  A series of N,N'-diphenyl and N-naphthyl-N'-phenyl guanidine derivatives was synthesized as potential N-methyl-D-aspartate (NMDA) receptor positron emission tomography (PET) ligands. The affinity of the different compounds was determined using in vitro receptor binding assays, and their log P values were estimated using HPLC analysis. The effect of N'-3 and N-3,5 substitution on affinity and lipophilicity was examined. The K-i values ranged from 1.87 to 839 nM, while log P values between 1.22 and 2.88 were observed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00235-4
• 作为产物：
  描述：

  1-isoselenocyanato-3,5-dimethylbenzene 在 1-[4-(diacetoxyiodo)benzyl]-3-methylimidazolium tetrafluoroborate 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3,5-dimethylphenyl)cyanamide
  参考文献：
  名称：

  Synthesis of Cyanamides from Isoselenocyanates Promoted by Recyclable Ionic Liquid-Supported (Diacetoxyiodo)Benzene

  摘要：

  在离子液体支持的高价碘（III）试剂 1-（4-二乙酰氧基碘苄基）-3-甲基咪唑四氟硼酸盐（[dibmim]+[BF4]-）的促进下，通过脱硒法从异硒氰酸酯一步合成氰酰胺。这种方法提供了一种简单、温和且对环境无害的方法来构建氰酰胺，而且产率很高。此外，粉末 Se 和 [dibmim]+[BF4]- 易于回收。这是[dibmim]+[BF4]- 用作脱硒剂的第一个实例。

  DOI：

  10.3184/174751915x14447479752475

文献信息

• Copper-Catalyzed One-Pot Synthesis of Unsymmetrical Arylurea Derivatives via Tandem Reaction of Diaryliodonium Salts with <i>N</i>-Arylcyanamide
  作者：Pengfei Li、Guolin Cheng、Hong Zhang、Xianxiang Xu、Jingyuan Gao、Xiuling Cui

  DOI：10.1021/jo501334u

  日期：2014.9.5

  efficient “one-pot” approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples

  已经提出了一种有效的“一锅法”，用于从N-芳基氰酰胺和二芳基碘鎓盐中制备多种取代的尿素。该两步过程涉及仲胺与二芳基碘鎓的弱碱促进的化学选择性芳基化和第二仲芳基碘鎓的铜催化的N-芳基氰酰胺的亲核加成。对于29个实施例，以高达91％的收率获得了各种不对称的芳基脲。
• [EN] COMPOUND, METHOD FOR PREPARING THE SAME, ORGANIC SEMICONDUCTING LAYER, ORGANIC ELECTRONIC DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE COMPRISING THE SAME<br/>[FR] COMPOSÉ, SON PROCÉDÉ DE PRÉPARATION, COUCHE SEMI-CONDUCTRICE ORGANIQUE, DISPOSITIF ÉLECTRONIQUE ORGANIQUE, DISPOSITIF D'AFFICHAGE ET DISPOSITIF D'ÉCLAIRAGE LE COMPRENANT
  申请人：NOVALED GMBH

  公开号：WO2019201621A1

  公开（公告）日：2019-10-24

  The present invention relates to a compound of Formula (I) wherein Ar1 is selected from substituted or unsubstituted C2 to C36heteroaryl and the group Ar1 is bound to the remaining structure represented by Formula (I) via one of its carbon atoms; Ar2 is selected from the group consisting of substituted or unsubstituted C6 to C36aryl and substituted or unsubstituted C4 to C36 heteroaryl comprising at least one heteroatom selected from 0, S and Se, wherein the heteroaryl group comprising at least one heteroatom selected from O, S and Se is bound to the remaining structure represented by Formula (I) via one of its carbon atoms; Ar3 is selected from the group consisting of substituted or unsubstituted C6 to C18 arylene and substituted or unsubstituted C3 to.C18 heteroarylene, wherein it is provided that the group Ar3 comprises not more than three fused rings; wherein, in case that one or more of Ar1, Ar2 and Ar3is substituted, the substituents are each independently selected from the group consisting of D, F, C1 to C20 linear alkyl, C3 to C20branched alkyl, C3 to C20 cyclic alkyl, C1 to C20 linear alkoxy, C3 to C20 branched alkoxy, linear fluorinated C1 to C12 allkyl, linear fluorinated C1 to C12 alkoxy, C3 to C12 branched fluorinated cyclic alkyl, C3 to C12 fluorinated cyclic allkyl, C3 to C12 fluorinated cyclic alkoxy, CN, RCN, C6 to C20, aryl, C2 to C20 heteroaryl, OR, SR, (C=0)R, (C=0)NR2, SiR3, (S=0)R, (S=0)2R, (P=0)R2; wherein each R is independently selected from C1to C20 linear alkyl, C1 to C20 alkoxy, C1to C20 thioalkyl, C3to C20 branched alkyl, C3 to C20 cyclic alkyl, C3 to C20 branched alkoxy, C3 to C20 cyclic alkoxy, C3 to C20 branched thioalkyl, C3 to C20 cyclic thioalkyl, C6 to C20 aryl and C2 to C20heteroaryl; and wherein Ar1 and Ar2 are selected differently from each other, a method for preparing the same, an organic semiconducting layer comprising the same, an organic electronic device comprising the same and a display device or a lighting device comprising the organic electronic device.

  本发明涉及一种化合物，其化学式为（I），其中Ar1选自取代或未取代的C2到C36杂芳基，并且基团Ar1通过其碳原子之一与化学式（I）表示的剩余结构结合；Ar2选自取代或未取代的C6到C36芳基和取代或未取代的包含至少一个来自O、S和Se的杂原子的C4到C36杂芳基，其中包含至少一个来自O、S和Se的杂原子的杂芳基通过其碳原子之一与化学式（I）表示的剩余结构结合；Ar3选自取代或未取代的C6到C18芳撑和取代或未取代的C3到C18杂芳撑，其中规定基团Ar3不含有超过三个融合环；在Ar1、Ar2和Ar3中有一个或多个被取代的情况下，取代基各自独立地选自D、F、C1到C20线性烷基、C3到C20支链烷基、C3到C20环烷基、C1到C20线性烷氧基、C3到C20支链烷氧基、线性氟代的C1到C12烷基、线性氟代的C1到C12烷氧基、C3到C12支链氟代环烷基、C3到C12氟代环烷基、C3到C12氟代环烷氧基、CN、RCN、C6到C20芳基、C2到C20杂芳基、OR、SR、（C=0）R、（C=0）NR2、SiR3、（S=0）R、（S=0）2R、（P=0）R2；其中每个R独立地选自C1到C20线性烷基、C1到C20烷氧基、C1到C20硫代烷基、C3到C20支链烷基、C3到C20环烷基、C3到C20支链烷氧基、C3到C20环烷氧基、C3到C20支链硫代烷基、C3到C20环硫代烷基、C6到C20芳基和C2到C20杂芳基；且Ar1和Ar2彼此不同选取，以及一种制备该化合物的方法，包含该化合物的有机半导体层，包含该化合物的有机电子器件，以及包含有机电子器件的显示器或照明器件。
• [EN] A PROCESS FOR THE PREPARATION OF THE COMPOUND N-(3,5-DIMETHYLPHENYL)-N'-(2-TRIFLUOROMETHYLPHENYL) GUANIDINE<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DU COMPOSÉ N-(3,5-DIMÉTHYLPHÉNYL)-N'-(2-TRIFLUOROMÉTHYLPHÉNYL)GUANIDINE
  申请人：CHEMO RES S L

  公开号：WO2017025560A1

  公开（公告）日：2017-02-16

  The present invention relates to a process for the preparation of the compound N-(3,5-dimethylphenyl)-N'-(2-trifluoromethylphenyl) guanidine of formula (I) which comprises reacting a salt of a compound of formula (II) or a mixture of the salt of the compound of formula (II) and a compound of formula (II) with a compound of formula (III), in the presence of a polar organic solvent; a crystalline solid form of the compound of formula (I), in particular crystalline solid form A; to a pharmaceutical composition comprising them; and to their use as a medicament, in particular to the treatment of a condition mediated by Rho-GTPase cell proteins.

  本发明涉及一种制备化合物N-(3,5-二甲基苯基)-N'-(2-三氟甲基苯基)脲的方法（式I），其中包括在极性有机溶剂的存在下，将化合物式（II）的盐或化合物式（II）的盐和化合物式（II）的混合物与化合物式（III）反应；化合物式（I）的晶体固态形式，特别是晶体固态形式A；以及包含它们的制药组合物和它们作为药物的用途，特别是用于治疗由Rho-GTP酶细胞蛋白介导的疾病。
• COMPOUND, METHOD FOR PREPARING THE SAME, ORGANIC SEMICONDUCTING LAYER, ORGANIC ELECTRONIC DEVICE, DISPLAY AND LIGHTING DEVICE COMPRISING THE SAME
  申请人：Novaled GmbH

  公开号：EP3556746A1

  公开（公告）日：2019-10-23

  The present invention relates to a compound of Formula (I) wherein Ar1 is selected from substituted or unsubstituted C2 to C36 heteroaryl and the group Ar1 is bound to the remaining structure represented by Formula (I) via one of its carbon atoms; Ar2 is selected from the group consisting of substituted or unsubstituted C6 to C36 aryl and substituted or unsubstituted C4 to C36 heteroaryl comprising at least one heteroatom selected from O, S and Se, wherein the heteroaryl group comprising at least one heteroatom selected from O, S and Se is bound to the remaining structure represented by Formula (I) via one of its carbon atoms; Ar3 is selected from the group consisting of substituted or unsubstituted C6 to C18 arylene and substituted or unsubstituted C3 to C18 heteroarylene, wherein it is provided that the group Ar3 comprises not more than three fused rings; wherein, in case that one or more of Ar1, Ar2 and Ar3 is substituted, the substituents are each independently selected from the group consisting of D, F, C1 to C20 linear alkyl, C3 to C20 branched alkyl, C3 to C20 cyclic alkyl, C1 to C20 linear alkoxy, C3 to C20 branched alkoxy, linear fluorinated C1 to C12 alkyl, linear fluorinated C1 to C12 alkoxy, C3 to C12 branched fluorinated cyclic alkyl, C3 to C12 fluorinated cyclic alkyl, C3 to C12 fluorinated cyclic alkoxy, CN, RCN, C6 to C20 aryl, C2 to C20 heteroaryl, OR, SR, (C=O)R, (C=O)NR2, SiR3, (S=O)R, (S=O)2R, (P=O)R2; wherein each R is independently selected from C1 to C20 linear alkyl, C1 to C20 alkoxy, C1 to C20 thioalkyl, C3 to C20 branched alkyl, C3 to C20 cyclic alkyl, C3 to C20 branched alkoxy, C3 to C20 cyclic alkoxy, C3 to C20 branched thioalkyl, C3 to C20 cyclic thioalkyl, C6 to C20 aryl and C2 to C20 heteroaryl; and wherein Ar1 and Ar2 are selected differently from each other, a method for preparing the same, an organic semiconducting layer comprising the same, an organic electronic device comprising the same and a display device or a lighting device comprising the organic electronic device.

  本发明涉及一种式 (I) 的化合物 其中 Ar1 选自取代或未取代的 C2 至 C36 杂芳基，且基团 Ar1 通过其一个碳原子与式 (I) 所代表的其余结构结合； Ar2 选自由取代或未取代的 C6 至 C36 芳基和包含至少一个选自 O、S 和 Se 的杂原子的取代或未取代的 C4 至 C36 杂芳基组成的基团，其中包含至少一个选自 O、S 和 Se 的杂原子的杂芳基通过其一个碳原子与式(I)所代表的剩余结构结合； Ar3 选自取代或未取代的 C6 至 C18 芳炔和取代或未取代的 C3 至 C18 杂芳炔组成的基团，其中，基团 Ar3 由不超过三个融合环组成； 其中，在 Ar1、Ar2 和 Ar3 中的一个或多个被取代的情况下，取代基各自独立选自 D、F、C1 至 C20 直链烷基、C3 至 C20 支链烷基、C3 至 C20 环烷基、C1 至 C20 直链烷氧基、C3 至 C20 支链烷氧基组成的组、直链氟代 C1 至 C12 烷基、直链氟代 C1 至 C12 烷氧基、C3 至 C12 支链氟代环烷基、C3 至 C12 氟代环烷基、C3 至 C12 氟代环烷氧基、CN、RCN、C6 至 C20 芳基、C2 至 C20 杂芳基、OR、SR、(C=O)R、(C=O)NR2、SiR3、(S=O)R、(S=O)2R、(P=O)R2；其中每个 R 独立选自 C1 至 C20 直链烷基、C1 至 C20 烷氧基、C1 至 C20 硫代烷基、C3 至 C20 支链烷基、C3 至 C20 环链烷基、C3 至 C20 支链烷氧基、C3 至 C20 环链烷氧基、C3 至 C20 支链硫代烷基、C3 至 C20 环链硫代烷基、C6 至 C20 芳基和 C2 至 C20 杂芳基；以及 其中 Ar1 和 Ar2 的选择互不相同、 一种制备上述物质、包含上述物质的有机半导体层、包含上述物质的有机电子器件以及包含上述有机电子器件的显示设备或照明设备的方法。
• Process for the preparation of the compound N-(3,5-dimethylphenyl)-N′-(2-trifluoromethylphenyl) guanidine
  申请人：CHEMO RESEARCH, S.L.

  公开号：US10343984B2

  公开（公告）日：2019-07-09

  The present invention relates to a process for the preparation of the compound N-(3,5-dimethylphenyl)-N′-(2-trifluoromethylphenyl) guanidine of formula (I) which comprises reacting a salt of a compound of formula (II) or a mixture of the salt of the compound of formula (II) and a compound of formula (II) with a compound of formula (III), in the presence of a polar organic solvent; a crystalline solid form of the compound of formula (I), in particular crystalline solid form A; to a pharmaceutical composition comprising them; and to their use as a medicament, in particular to the treatment of a condition mediated by Rho-GTPase cell proteins.

  本发明涉及一种制备式(I)化合物N-(3,5-二甲基苯基)-N′-(2-三氟甲基苯基)胍的工艺，该工艺包括在极性有机溶剂存在下，使式(II)化合物的盐或式(II)化合物的盐和式(II)化合物的混合物与式(III)化合物反应；式（I）化合物的结晶固体形式，特别是结晶固体形式 A；包含它们的药物组合物；以及它们作为药物的用途，特别是治疗由 Rho-GTPase 细胞蛋白介导的病症。