5-(三氟甲氧基)苯并咪唑-2(3H)-酮 | 877681-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 5-(三氟甲氧基)苯并咪唑-2(3H)-酮
• 英文名称: 5-(trifluoromethoxy)-1,3-dihydro-2H-benzo[d]imidazol-2-one
• 英文别名: 5-[(trifluoromethyl)oxy]-1,3-dihydro-2H-benzimidazol-2-one；1,3-Dihydro-5-(trifluoromethoxy)-2H-benzimidazol-2-one；5-(trifluoromethoxy)-1,3-dihydrobenzimidazol-2-one
• CAS: 877681-12-4
• 化学式: C₈H₅F₃N₂O₂
• 分子量: 218.135
• InChiKey: MTWMCTUKHLUSMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(Trifluoromethoxy)benzoimidazol-2(3H)-one
Synonyms: 5-(Trifluoromethoxy)-1H-benzo[d]imidazol-2(3H)-one

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-(Trifluoromethoxy)benzoimidazol-2(3H)-one
CAS number: 877681-12-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H5F3N2O2
Molecular weight: 218.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen fluoride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(三氟甲氧基)苯并咪唑-2(3H)-酮 在 potassium carbonate 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 20.67h， 生成 (3aR,6aR)-1-(6-(trifluoromethoxy)-1H-benzo[d]imidazol-2-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carbonitrile
  参考文献：
  名称：

  [EN] CYANOPYRROLIDINE DERIVATIVES WITH ACTIVITY AS INHIBITORS OF USP30
  [FR] DÉRIVÉS DE CYANOPYRROLIDINE AYANT UNE ACTIVITÉ EN TANT QU'INHIBITEURS DE L'USP 30

  摘要：

  本发明涉及一类具有抑制去泛素化酶活性的替代氰基吡咯烷化合物，特别是泛素C端水解酶30或泛素特异性肽酶30（USP30），在包括癌症和涉及线粒体功能障碍的各种治疗领域中具有用途。

  公开号：

  WO2018060742A1
• 作为产物：
  描述：

  2-硝基-4-(三氟甲氧基)乙酰苯胺 在 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 70.0 ℃ 、310.27 kPa 条件下， 反应 4.0h， 生成 5-(三氟甲氧基)苯并咪唑-2(3H)-酮
  参考文献：
  名称：

  Benzimidazolones: A New Class of Selective Peroxisome Proliferator-Activated Receptor γ (PPARγ) Modulators

  摘要：

  A series of benzimidazolone carboxylic acids and oxazolidinediones were designed and synthesized in search of selective PPAR gamma modulators (SPPAR gamma Ms) as potential therapeutic agents for the treatment of type II diabetes mellitus (T2DM) with improved safety profiles relative to rosiglitazone and pioglitazone, the currently marketed PPAR gamma full agonist drugs. Structure activity relationships of these potent and highly selective SPPAR gamma Ms were studied with a focus on their unique profiles as partial agonists or modulators. A variety of methods, such as X-ray aystallographic analysis, PPAR gamma transactivation coactivator profiling, gene expression profiling, and mutagenesis studies, were employed to reveal the differential interactions of these new analogues with PPAR gamma receptor in comparison to full agonists. In rodent models of T2DM, benzimidazolone analogues such as (5R)-5-(3-{[3-(5-methoxybenzisoxazol-3-yl)benzimidazol-1-yl]methyl}phenyl)-5-methyloxazolidinedione (Si) demonstrated efficacy equivalent to that of rosiglitazone. Side effects, such as fluid retention and heart weight gain associated with PPAR gamma full agonists, were diminished with 51 in comparison to rosiglitazone based on studies in two independent animal models.

  DOI：

  10.1021/jm201061j

文献信息

• Benzoureas Having Anti-Diabetic Activity
  申请人：Lui Weiguo

  公开号：US20080076810A1

  公开（公告）日：2008-03-27

  Benzourea compounds of Formula I having aryl-(CH 2 ) x -oxazolidinedione or aryl-(CH 2 ) x -thiazolidinedione substituents on one of the N atoms of the benzourea ring, wherein x is 0 or 1, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia and other symptoms such as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity, that are often associated with type 2 diabetes.

  具有在苯甲酰脲环的一个N原子上具有芳基-(CH2)x-噁唑啉二酮或芳基-( )x-噻唑啉二酮取代基的公式I的苯甲酰脲化合物，其中x为0或1，是PPAR gamma激动剂或部分激动剂，并且在治疗和控制II型糖尿病，包括高血糖和其他症状，如血脂异常、高脂血症、高胆固醇血症、高三酰甘油血症和肥胖症方面非常有用，这些症状通常与2型糖尿病相关。
• Benzimidazoles With A Hetero Spiro-Decane Residue As NPY-Y5 Antagonists
  申请人：Barton Nicholas Paul

  公开号：US20100216821A1

  公开（公告）日：2010-08-26

  The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salts, solvates, stereoisomers thereof, R 1 may be C 1 -C 4 alkyl, aryl or heteroaryl, which may be substituted by one or more: halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, cyano; R 2 may be halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, cyano, nitro; or aryl, heteroaryl or heterocycle, which may be substituted by one or more: halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, cyano; or R 2 may correspond to —O—R 3 ; R 3 is a 6-membered aromatic carbocyclic ring which may contain 1 or 2 nitrogen X is carbon or oxygen; Z is carbon or nitrogen; G is a fused 6-membered aromatic carbocyclic ring which may contain 1 or 2 nitrogen; m may be 0 or an integer ranging from 1 to 4; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as NPY-Y5 receptor antagonists.

  本发明涉及式（I）的化合物，或其药学上可接受的盐，溶剂化合物和立体异构体，其中R1可以是C1-C4烷基，芳基或杂芳基，可以被一个或多个卤素，C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，C1-C4卤代烷氧基，氰基取代；R2可以是卤素，C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，C1-C4卤代烷氧基，氰基，硝基或芳基，杂芳基或杂环，可以被一个或多个卤素，C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，C1-C4卤代烷氧基，氰基取代；或者R2可以对应于—O—R3；R3是一个含有1或2个氮原子的6元芳香环；X是碳或氧；Z是碳或氮；G是一个融合的含有1或2个氮原子的6元芳香环；m可以是0或一个范围在1到4之间的整数；本发明还涉及制备这些化合物的方法，用于这些方法的中间体，包含它们的制药组合物以及它们作为NPY-Y5受体拮抗剂在治疗中的应用。
• Cyanopyrrolidine derivatives with activity as inhibitors of USP30
  申请人：MISSION THERAPEUTICS LIMITED

  公开号：US11084821B2

  公开（公告）日：2021-08-10

  The present invention relates to a class of substituted-cyanopyrrolidines of Formula (I) with activity as inhibitors of deubiquitilating enzymes, in particular, ubiquitin C-terminal hydrolase 30 or ubiquitin specific peptidase 30 (USP30), having utility in a variety of therapeutic areas including cancer and conditions involving mitochondrial dysfunction.

  本发明涉及一类具有去泛素化酶（特别是泛素 C 端水解酶 30 或泛素特异性肽酶 30 (USP30)）抑制剂活性的式（I）取代氰基吡咯烷类化合物，该化合物可用于多种治疗领域，包括癌症和涉及线粒体功能障碍的疾病。
• WO2008/129007
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2006/50148
  申请人：——

  公开号：——

  公开（公告）日：——