2,5-双(三氟甲基)苯酚 | 779-88-4

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 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-双(三氟甲基)苯酚
• 英文名称: 2,5-bis-(trifluoromethyl)phenol
• 英文别名: 2-Hydroxy-1,4-bis-(trifluormethyl)-benzol；2,5-Bis(trifluoromethyl)phenol
• CAS: 779-88-4
• 化学式: C₈H₄F₆O
• 分子量: 230.11
• InChiKey: OJOPQGWFLQVKDU-UHFFFAOYSA-N

物化性质

• 熔点：
  55 °C
• 沸点：
  185.2±35.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2908199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-三氟甲基水杨酸	4-trifluoromethylsalicylic acid	328-90-5	C8H5F3O3	206.121

反应信息

• 作为反应物：
  描述：

  2,5-双(三氟甲基)苯酚 在 sodium hydroxide 作用下， 生成 4-三氟甲基水杨酸
  参考文献：
  名称：

  Shein,S.M.; Krasnosel'skaya,M.I., Journal of general chemistry of the USSR, 1964, vol. 34, p. 3427 - 3430

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二三氟甲基苯胺 生成 2,5-双(三氟甲基)苯酚
  参考文献：
  名称：

  Shein,S.M.; Krasnosel'skaya,M.I., Journal of general chemistry of the USSR, 1964, vol. 34, p. 3427 - 3430

  摘要：

  DOI：

文献信息

• 含有三氟甲基的吡嗪酰胺类化合物及其制备 方法和应用以及杀菌剂
  申请人：华中师范大学

  公开号：CN109666004B

  公开（公告）日：2020-08-21

  本发明涉及农药杀菌剂领域，公开了含有三氟甲基的吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂，该化合物具有式(I)或式(II)所示的结构。本发明通过引入NNF‑0721中的吡嗪环片段和具有广泛生物活性的二苯醚片段，设计出了具有全新结构的含有三氟甲基的吡嗪酰胺类化合物，该含有三氟甲基的吡嗪酰胺类化合物能够作为全新的琥珀酸脱氢酶抑制剂或杀菌剂。
• Studies to Further Investigate the Inhibition of Human Liver Microsomal CYP2C8 by the Acyl-β-Glucuronide of Gemfibrozil
  作者：S. M. Jenkins、T. Zvyaga、S. R. Johnson、J. Hurley、A. Wagner、R. Burrell、W. Turley、J. E. Leet、T. Philip、A. D. Rodrigues

  DOI：10.1124/dmd.111.041947

  日期：2011.12

  In previous studies, gemfibrozil acyl-β-glucuronide, but not gemfibrozil, was found to be a mechanism-based inhibitor of cytochrome P450 2C8. To better understand whether this inhibition is specific for gemfibrozil acyl-β-glucuronide or whether other glucuronide conjugates are potential substrates for inhibition of this enzyme, we evaluated several pharmaceutical compounds (as their acyl glucuronides) as direct-acting and metabolism-dependent inhibitors of CYP2C8 in human liver microsomes. Of 11 compounds that were evaluated as their acyl glucuronide conjugates, only gemfibrozil acyl-β-glucuronide exhibited mechanism-based inhibition, indicating that CYP2C8 mechanism-based inhibition is very specific to certain glucuronide conjugates. Structural analogs of gemfibrozil were synthesized, and their glucuronide conjugates were prepared to further examine the mechanism of inhibition. When the aromatic methyl groups on the gemfibrozil moiety were substituted with trifluoromethyls, the resulting glucuronide conjugate was a weaker inhibitor of CYP2C8 and mechanism-based inhibition was abolished. However, the glucuronide conjugates of monomethyl gemfibrozil analogs were mechanism-based inhibitors of CYP2C8, although not as potent as gemfibrozil acyl-β-glucuronide itself. The ortho -monomethyl analog was a more potent inhibitor than the meta -monomethyl analog, indicating that CYP2C8 favors the ortho position for oxidation and potential inhibition. Molecular modeling of gemfibrozil acyl-β-glucuronide in the CYP2C8 active site is consistent with the ortho -methyl position being the favored site of covalent attachment to the heme. Moreover, hydrogen bonding to four residues (Ser100, Ser103, Gln214, and Asn217) is implicated.

  在以前的研究中，发现吉非罗齐酰基-β-葡萄糖醛酸苷，而不是吉非罗齐，是细胞色素 P450 2C8 的一种基于机制的抑制剂。为了更好地了解这种抑制作用是否是对吉非罗齐酰基-β-葡萄糖醛酸的特异性抑制，或者其他葡萄糖醛酸结合物是否是抑制这种酶的潜在底物，我们评估了几种药物化合物（作为其酰基葡萄糖醛酸）作为 CYP2C8 在人肝微粒体中的直接作用和代谢依赖性抑制剂。在以酰基葡萄糖醛酸苷共轭物形式进行评估的 11 种化合物中，只有吉非罗齐酰基-β-葡萄糖醛酸苷表现出基于机理的抑制作用，这表明基于机理的 CYP2C8 抑制作用对某些葡萄糖醛酸苷共轭物具有很强的特异性。为了进一步研究吉非罗齐的抑制机制，我们合成了吉非罗齐的结构类似物，并制备了它们的葡萄糖醛酸苷共轭物。当吉非罗齐分子上的芳香甲基被三氟甲基取代时，得到的葡萄糖醛酸苷共轭物对 CYP2C8 的抑制作用较弱，基于机制的抑制作用被取消。然而，单甲基吉非罗齐类似物的葡萄糖醛酸苷结合物是基于机制的 CYP2C8 抑制剂，尽管其效力不如吉非罗齐酰基-β-葡萄糖醛酸苷本身。正-单甲基类似物是比偏-单甲基类似物更有效的抑制剂，这表明 CYP2C8 更倾向于正位氧化和潜在抑制。吉非罗齐酰基-β-葡萄糖醛酸在 CYP2C8 活性位点的分子模型与正-甲基位点是与血红素共价连接的有利位点相一致。此外，与四个残基（Ser100、Ser103、Gln214 和 Asn217）的氢键也有关联。
• Peptides capable of inhibiting the activity of HIV protease, their preparation and their therapeutic use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0587311A1

  公开（公告）日：1994-03-16

  Compounds of formula (I) : [wherein: R¹ is hydrogen, alkyl, aralkyl, -CORa, -CORb, -CSRa, -CSRb, -SO₂Rb, -CONHRb, -CSNHRb, -CONRbRb or -CSNRbRb; R² is hydrogen or alkyl; R³ is hydrogen, alkylidene, substituted alkyl, or Rb; R⁴ is optionally substituted alkyl, cycloalkyl, or aryl; R⁵ is RbO-, RbRbN-, RbHN-, aralkyloxycarbonyloxy or aralkyloxycarbonylamino, or R⁵ is -(CH₂)p-D-(CH₂)r- [where D is a single bond, carbonyl, oxygen, sulphur, -NH-, -(CH₂=CH₂)- or -NHCO-; and p and r are each 0 or an integer from 1 to 5]; A is -(CH₂)m-B-(CH₂)n- [where B is a single bond, carbonyl, oxygen, sulphur, -NH-, -(CH₂=CH₂)- or -NHCO-; and m and n are each 0 or an integer from 1 to 5]; Ra is alkoxy, aralkyloxy, aryloxy or alkoxycarbonyl; Rb is optionally substituted alkyl, cycloalkyl, heterocyclic, aryl or arylalkenyl]; and pharmaceutically acceptable salts and esters thereof and pro-drugs therefor, have the ability to inhibit the activity of HIV protease and may thus be used for the treatment and prophylaxis of AIDS.

  化合物的化学式为(I)：[其中：R¹为氢，烷基，芳基烷基，-CORa，-CORb，-CSRa，-CSRb，-SO₂Rb，-CONHRb，-CSNHRb，-CONRbRb或-CSNRbRb；R²为氢或烷基；R³为氢，烷基亚甲基，取代烷基或Rb；R⁴为可选取代的烷基，环烷基或芳基；R⁵为RbO-，RbRbN-，RbHN-，芳基烷氧羰氧基氧或芳基烷氧羰氨基，或R⁵为-(CH₂)p-D-(CH₂)r- [其中D为单键，酰基，氧，硫，-NH-，-(CH₂=CH₂)-或-NHCO-；p和r分别为0或1到5的整数]；A为-(CH₂)m-B-(CH₂)n- [其中B为单键，酰基，氧，硫，-NH-，-(CH₂=CH₂)-或-NHCO-；m和n分别为0或1到5的整数]；Ra为烷氧基，芳基烷氧基，芳氧基或烷氧羰基；Rb为可选取代的烷基，环烷基，杂环，芳基或芳基烷烯基]；以及其药学上可接受的盐和酯以及其前药，具有抑制HIV蛋白酶活性的能力，因此可用于治疗和预防艾滋病。
• High-purity (fluoroalkyl)benzene derivative and process for producing the same
  申请人：Hidaka Toshio

  公开号：US20060167324A1

  公开（公告）日：2006-07-27

  The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.

  本发明生产(氟烷基)苯衍生物的过程包括以下步骤：将烷基苯衍生物中3至12族过渡金属的总含量以金属原子计减少至500 ppm或以下；通过光卤化反应卤化纯化后的烷基苯衍生物的支链烷基，得到(卤烷基)苯衍生物；使用10摩尔或更高量的HF对(卤烷基)苯衍生物进行卤素-氟交换。本发明生产的(氟烷基)苯衍生物中杂质含量如残留卤素和残留金属得到了降低，可用作功能化学产品的中间体，用于药品和电子材料等应用。
• Investigation on voltage loss in organic triplet photovoltaic devices based on Ir complexes
  作者：Yingzhi Jin、Jie Xue、Juan Qiao、Fengling Zhang

  DOI：10.1039/c9tc04914b

  日期：——

  A higher V_oc is achieved in Ir(FOtbpa)₃-based devices despite a lower energy charge transfer state compared to Ir(Ftbpa)₃-based devices, which is attributed to the reduced radiative and non-radiative recombination.

  尽管与基于Ir（Ftbpa）₃的器件相比，基于Ir（FOtbpa）₃的器件具有较低的能量电荷转移态，但由于较小的辐射和非辐射复合，Ir（FOtbpa）₃的器件实现了更高的V_oc。