2,5-二氟-4-碘苯胺 | 155906-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二氟-4-碘苯胺
• 英文名称: 2,5-difluoro-4-iodoaniline
• CAS: 155906-13-1
• 化学式: C₆H₄F₂IN
• 分子量: 255.006
• InChiKey: DQTJNHXTFILGGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335

反应信息

• 作为反应物：
  描述：

  2,5-二氟-4-碘苯胺 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 生成 N-(4-cyclopropyl-2,5-difluorophenyl)-4-methyl-5-(thiazol-2-yl)-1H-pyrrol-3-sulfonamide
  参考文献：
  名称：

  GPR17 MODULATORS AND USES THEREOF

  摘要：

  Disclosed herein are compounds capable of modulating GPR17 and pharmaceutical compositions of such compounds and methods of treatment for conditions, e.g., neurodegenerative diseases or demyelinating diseases, using such pharmaceutical compositions.

  公开号：

  WO2024104462A1
• 作为产物：
  描述：

  4-溴-2,5-二氟苯胺 在 copper(l) iodide 、 N,N-二甲基乙二胺 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以71%的产率得到2,5-二氟-4-碘苯胺
  参考文献：
  名称：

  Identification of New Potent GPR119 Agonists by Combining Virtual Screening and Combinatorial Chemistry

  摘要：

  Virtual screening in a huge collection of virtual combinatorial libraries has led to the identification of two new structural classes of GPR119 agonists with submicromolar in vitro potencies. Herein, we describe the virtual screening process involving feature trees fragment space searches followed by a 3D postprocessing step. The in silico findings were then filtered and prioritized, and finally, combinatorial libraries of target molecules were synthesized. Furthermore the so-called "activity-anchor principle" is introduced as an element to increase the chance to generate true hits. An activity anchor is a structural element expected to provide key contributions to a certain biological activity. Application of this technique has led to the discovery of two new GPR119-agonist hit series, one of which was further optimized to progress as a novel lead class.

  DOI：

  10.1021/jm301549a

文献信息

• p-Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles
  作者：Larisa Politanskaya、Evgeny Tretyakov

  DOI：10.1055/s-0036-1591504

  日期：2018.2

  conditions, and uses readily available starting compounds (trimethylsilylarylacetylene derivatives). The reaction provides access to amino-substituted acetophenones, which may serve as precursors for the synthesis of polyfluorinated azaheterocycles, having potential anticarcinogenic activity. A simple and efficient approach to the synthesis of fluorinated amino-substituted acetophenones in good to excellent

  摘要 报道了一种简单有效的合成氟化氨基取代的苯乙酮的方法，收率很好。所提出方法的核心是在存在对乙磺酸（p -TSA）经过乙炔基苯胺形成阶段的情况下，将Me 3 Si–C≡C–部分转化为MeC（= O）–基团。该反应是无金属的，在温和的条件下进行，并使用容易获得的起始化合物（三甲基甲硅烷基芳基乙炔衍生物）。该反应提供了获得氨基取代的苯乙酮的途径，其可以用作合成多氟氮杂杂环的前体，具有潜在的抗癌活性。 报道了一种简单有效的合成氟化氨基取代的苯乙酮的方法，收率很好。所提出方法的核心是在存在对乙磺酸（p -TSA）经过乙炔基苯胺形成阶段的情况下，将Me 3 Si–C≡C–部分转化为MeC（= O）–基团。该反应是无金属的，在温和的条件下进行，并使用容易获得的起始化合物（三甲基甲硅烷基芳基乙炔衍生物）。该反应提供了获得氨基取代的苯乙酮的途径，其可以用作合成多氟氮杂杂环的前体，具有潜在的抗癌活性。
• [EN] (AZA)INDOLE-, BENZOTHIOPHENE-, AND BENZOFURAN-3-SULFONAMIDES<br/>[FR] (AZA)INDOLE, BENZOTHIOPHÈNE ET BENZOFURAN-3-SULFONAMIDES
  申请人：UCB PHARMA GMBH

  公开号：WO2018122232A1

  公开（公告）日：2018-07-05

  Disclosed are sulfonamide compounds with GPR17 modulating properties, which are useful for treating or preventing a variety of CNS and other diseases, in particular for preventing and treating myelinating diseases or disorders.

  揭示了具有GPR17调节特性的磺胺类化合物，可用于治疗或预防各种中枢神经系统和其他疾病，特别是用于预防和治疗髓鞘疾病或紊乱。
• General and efficient synthesis of polyfluorinated 2-aminotolans and 2-arylindoles
  作者：Larisa V. Politanskaya、Vitalij D. Shteingarts、Evgeny V. Tretyakov

  DOI：10.1016/j.jfluchem.2016.06.010

  日期：2016.8

  It was established here that cross-coupling of polyfluorinated 2-iodoanilines with arylacetylenes in MeCN in the presence catalytic amounts of Pd(PPh3)2Cl2, CuI and Et3N produces the corresponding 2-aminotolans although their yields are decreased from 98% to 40% with increasing fluorination of the substrates. It was shown that the 2-aminotolans with six or fewer fluorine atoms in their rings can be

  在此确定，在催化量为Pd（PPh 3）2 Cl 2，CuI和Et 3 N的存在下，MeCN中多氟2-碘苯胺与芳基乙炔的交叉偶联产生了相应的2-氨基tolan，尽管它们的收率从98降低了。随着底物氟化作用的增加，碳纤维的重量百分比增加到40％到40％。结果表明，在环中具有6个或更少氟原子的2-氨基tolan可以通过在含p的乙醇中加热而被杂环化-TSA产生相应的多氟吲哚。在存在KOH的情况下，环中含大量氟原子的tolan的环化最有效，导致目前最多含8个氟原子的2-苯基吲哚。
• Substituted sulfonylaminoarylmethyl cyclopropanecarboxamide as VR1 receptor antagonists
  申请人：Hanazawa Takeshi

  公开号：US20060211741A1

  公开（公告）日：2006-09-21

  This invention provides a compound of the formula (I): wherein A and B are independently CR 12 or N; D and E are each independently CR 9 or N; R 1 represents (C 1 -C 6 )alkyl; R 2 represents hydrogen, halogen, hydroxy, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy or (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl; R 3 , R 4 , R 5 , R 6 , R 10 and R 11 each independently represent hydrogen, halogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, hydroxy(C 1 -C 6 )alkyl or (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl; or R 3 and R 4 are taken together with the carbon atom to which they are attached to form a 3- to 7-membered carbocyclic ring or heterocyclic ring in which one or two non-adjacent carbon atoms are optionally replaced by an oxygen atom, a sulfur atom or NH; R 7 and R 9 each independently represent hydrogen, halogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, hydroxy(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )alkylsulfonyl, NH 2 , [(C 1 -C 6 )alkyl]NH—, [(C 1 -C 6 )alkyl] 2 N—, H 2 N—(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl-NH—(C 1 -C 6 )alkoxy, [(C 1 -C 6 )alkyl] 2 N(C 1 -C 6 )alkoxy; H 2 N—(C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 C 6 )alkyl-NH—(C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkyl] 2 N(C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl or 5- or 6-membered heterocyclic ring containing at least one nitrogen atom; R 8 represents halogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, hydroxy(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylsulfonyl, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, [(C 1 -C 6 )alkyl]NH— or [(C 1 -C 6 )alkyl] 2 N—; or R 7 and R 8 , when E is CR 9 , are taken together with the carbon atoms to which they are attached form a 5-8 membered carbocyclic or heterocyclic ring, in which one or two non-adjacent carbon atoms are optionally replaced by oxygen, sulfur, N or NH groups, wherein the carbocyclic ring or the heterocyclic ring is unsubstituted or substituted with one or more substituents each independently selected from the group consisting of hydroxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and hydroxy(C 1 -C 6 )alkyl; and R 12 represents hydrogen, halogen, (C 1 -C 6 )alkyl or hydroxy(C 1 -C 6 )alkyl; or a pharmaceutically acceptable salt or solvate thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of VR1 receptor such of pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.

  这项发明提供了一个化合物的结构式(I)：其中A和B分别独立地为CR12或N；D和E分别独立地为CR9或N；R1代表(C1-C6)烷基；R2代表氢、卤素、羟基、(C1-C6)烷基、卤代(C1-C6)烷基、羟基(C1-C6)烷基、(C1-C6)氧烷基或(C1-C6)氧烷基-(C1-C6)烷基；R3、R4、R5、R6、R10和R11分别独立地代表氢、卤素、(C1-C6)烷基、卤代(C1-C6)烷基、(C1-C6)氧烷基、羟基(C1-C6)烷基或(C1-C6)氧烷基-(C1-C6)烷基；或者R3和R4一起与它们连接的碳原子形成一个3-至7-成员的碳环或杂环，其中一个或两个非相邻的碳原子可以选择性地被氧原子、硫原子或NH取代；R7和R9分别独立地代表氢、卤素、(C1-C6)烷基、卤代(C1-C6)烷基、羟基(C1-C6)烷基、(C1-C6)氧烷基、羟基(C1-C6)氧烷基、(C1-C6)氧烷基-(C1-C6)烷基、(C1-C6)氧烷基-(C1-C6)氧烷基、(C1-C6)烷基硫、(C1-C6)烷基亚硫基、(C1-C6)烷基磺基、NH2、[(C1-C6)烷基]NH—、[(C1-C6)烷基]2N—、H2N—(C1-C6)氧烷基、(C1-C6)烷基-NH—(C1-C6)氧烷基、[(C1-C6)烷基]2N(C1-C6)氧烷基； —(C1-C6)氧烷基-(C1-C6)烷基、(C1C6)烷基-NH—(C1-C6)氧烷基-(C1-C6)烷基、[(C1-C6)烷基]2N(C1-C6)氧烷基-(C1-C6)烷基或含有至少一个氮原子的5-或6-成员杂环，R8代表卤素、(C1-C6)烷基、卤代(C1-C6)烷基、羟基(C1-C6)烷基、(C1-C6)氧烷基、羟基(C1-C6)氧烷基、(C1-C6)氧烷基-(C1-C6)烷基、(C1-C6)氧烷基-(C1-C6)氧烷基、卤代(C1-C6)烷基磺基、卤代(C1-C6)烷基亚硫基、卤代(C1-C6)烷基氧基、卤代(C1-C6)烷基硫基、[(C1-C6)烷基]NH—或[(C1-C6)烷基]2N—；或者当E为CR9时，R7和R8一起与它们连接的碳原子形成一个5-8成员的碳环或杂环，其中一个或两个非相邻的碳原子可以选择性地被氧、硫、N或NH基团取代，其中碳环或杂环未取代或取代有一个或多个取代基，每个取代基独立地选自羟基、(C1-C6)烷基、(C1-C6)氧烷基和羟基(C1-C6)烷基；R12代表氢、卤素、(C1-C6)烷基或羟基(C1-C6)烷基；或其药学上可接受的盐或溶剂。这些化合物对于治疗由VR1受体过度激活引起的疾病状况，如哺乳动物中的疼痛等，是有用的。这项发明还提供了包含上述化合物的药物组合物。
• Tolane derivatives, liquid crystal compositions containing the
  申请人：Seiko Epson Corporation

  公开号：US05356558A1

  公开（公告）日：1994-10-18

  A tolane derivative, a liquid crystal composition containing the derivative, and a liquid crystal display device including the composition, in which the tolane derivative is represented by the following general formula: ##STR1## wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms, and each of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represents a fluorine atom or a hydrogen atom wherein at least one X represents a fluorine atom, and Y represents a nitrile group or a straight-chain alkyl group having 1 to 10 carbon atoms. By blending the above-described compound with a general liquid crystal composition, a liquid crystal composition is provided which exhibits a wide practical temperature range as well as a large anisotropy of refractive index.

  一种甲苯衍生物，包含该衍生物的液晶组合物，以及包括该组合物的液晶显示装置，其中该甲苯衍生物由以下一般式表示：##STR1## 其中R代表具有1至10个碳原子的直链烷基基团，每个X.sub.1、X.sub.2、X.sub.3和X.sub.4代表氟原子或氢原子，其中至少一个X代表氟原子，Y代表腈基或具有1至10个碳原子的直链烷基基团。通过将上述化合物与一般液晶组合物混合，提供了一种液晶组合物，其具有广泛的实用温度范围以及较大的折射率各向异性。