2-氟-6-硝基苯甲醛 | 1644-82-2

• 物质功能分类: 有机原料 - 醛类化合物
• 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-氟-6-硝基苯甲醛
• 中文别名: 一缩二乙二醇一(2-乙基已基)醚；二甘醇(2-乙己基)醚；2-乙己基卡必醇；二甘醇一(2-乙己基)醚；二乙二醇单辛醚；一缩二乙二醇单(2-乙基已基)醚；2-{(2-[(2-乙基己基)氧基]乙氧基}乙醇；二甘醇单(2-乙己基)醚
• 英文名称: 2-fluoro-6-nitrobenzaldehyde
• CAS: 1644-82-2
• 化学式: C₇H₄FNO₃
• 分子量: 169.112
• InChiKey: LMTKLMMRJDNPFT-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63℃
• 沸点：
  287℃
• 密度：
  1.443
• 闪点：
  127℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2913000090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  温度控制在2至8℃，并处于惰性气体环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Fluoro-6-nitrobenzaldehyde
Synonyms:

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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: 2-Fluoro-6-nitrobenzaldehyde
CAS number: 1644-82-2

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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, refrigerated.
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: C7H4FNO3
Molecular weight: 169.1

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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：

  2-氟-6-硝基苯甲醛 在 甲醇 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 4-硝基-苯并[b]噻吩-2-羧酸
  参考文献：
  名称：

  苯并[b]噻吩-1,1-二氧化物衍生物作为新型 PHGDH 共价抑制剂的鉴定

  摘要：

  丝氨酸生物合成的增加为肿瘤发生和转移提供了许多优势。磷酸甘油酸脱氢酶 (PHGDH) 是丝氨酸生物发生中的限速酶，在多种肿瘤中表现出高活性，并成为癌症治疗的有希望的靶点。通过筛选我们的内部化合物库，我们确定该化合物是一种有效的 PHGDH 抑制剂 (IC = 1.98 ± 0.66 µM)。随后对结构活性关系的探索发现了能够增强酶抑制活性的化合物 (IC = 0.29 ± 0.02 μM)。此外，对过度表达 PHGDH 的 MDA-MB-468、NCI-H1975、HT1080 和 PC9 细胞的增殖表现出强大的抑制作用。此外，使用[UC]-葡萄糖示踪测定，发现可以减少 MDA-MB-468 细胞中葡萄糖衍生丝氨酸的产生。最后，基于质谱的肽分析、诱变实验和分子对接研究共同表明与PHGDH的Cys421形成共价键。

  DOI：

  10.1016/j.bioorg.2024.107330
• 作为产物：
  描述：

  5-氟-2-硝基苄溴 在 N-甲基吗啉氧化物 作用下， 以 乙腈 为溶剂， 以75%的产率得到2-氟-6-硝基苯甲醛
  参考文献：
  名称：

  [DE] HETEROCYCLYL-SUBSTITUIERTE DIHYDROCHINAZOLINE UND IHRE VERWENDUNG ALS ANTIVIRALE MITTEL
  [EN] HETEROCYCLYL-SUBSTITUTED DIHYDROQUINAZOLINES AND USE THEREOF AS AN ANTIVIRAL AGENT
  [FR] DIHYDROQUINAZOLINES SUBSTITUEES PAR HETEROCYCLYLE ET LEUR UTILISATION COMME ANTIVIRAUX

  摘要：

  这项发明涉及式(I)的杂环取代二氢喹啉，以及其制备方法和用途，用于制备用于治疗和/或预防疾病的药物，特别是用作抗病毒药物，特别是对抗巨细胞病毒。

  公开号：

  WO2004099212A1

文献信息

• [EN] THIAZOLES AS MODULATORS OF RORyt<br/>[FR] THIAZOLES UTILISÉS COMME MODULATEURS DE RORYT
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2016069976A1

  公开（公告）日：2016-05-06

  The present invention comprises compounds of Formula I. Formula I wherein: R1, R2, R3, R4, R5, R7, R8, and (A) are defined in the specification. The invention also comprises a compound of Formula I for use in a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a compound for use in a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.

  本发明包括公式I的化合物。公式I中：R1、R2、R3、R4、R5、R7、R8和(A)在说明书中定义。该发明还包括用于治疗或改善综合症、紊乱或疾病的公式I化合物，其中所述综合症、紊乱或疾病为类风湿性关节炎或银屑病。该发明还包括用于通过管理治疗有效量的至少一个权利要求1的化合物来调节哺乳动物中RORγt活性的化合物。
• [EN] 1,2,4-OXADIAZOLE SUBSTITUTED PIPERIDINE AND PIPERAZINE DERIVATIVES AS SMO ANTAGONISTS<br/>[FR] DÉRIVÉS DE PIPÉRIDINE OU PIPÉRAZINE SUBSTITUÉS PAR 1,2,4-OXADIAZOLE COMME ANTAGONISTES DE SMO
  申请人：ANGELETTI P IST RICHERCHE BIO

  公开号：WO2010013037A1

  公开（公告）日：2010-02-04

  The present invention relates to compounds of formula (I): and pharmaceutically acceptable salts, stereoisomers or tautomers thereof which are inhibitors of the Sonic Hedgehog pathway, in particular Smo antagonists. Thus the compounds of this invention are useful for the treatment of diseases associated with abnormal hedgehog pathway activation, including cancer, for example basal cell carcinoma, medulloblastoma, prostate, pancreatic, breast, colon, bone and small cell lung cancers, and cancers of the upper GI tract.

  本发明涉及式(I)的化合物及其药学上可接受的盐、立体异构体或互变异构体，这些化合物是Sonic Hedgehog途径的抑制剂，特别是Smo拮抗剂。因此，本发明的化合物对治疗与异常Hedgehog途径激活相关的疾病有用，包括癌症，例如基底细胞癌、髓母细胞瘤、前列腺、胰腺、乳腺、结肠、骨骼和小细胞肺癌，以及上消化道的癌症。
• Heterocyclyl-substituted dihydroquinazolines and their use as antiviral agents
  申请人：Wunberg Tobias

  公开号：US20070185121A1

  公开（公告）日：2007-08-09

  The invention relates to heterocyclyl-substituted dihydroquinazolines of formula (I), to processes for their preparation, to medicaments containing them, and to methods for the treatment and/or prophylaxis of diseases, in particular, for use as anti-viral agents, in particular, against cytomegaloviruses.

  这项发明涉及公式（I）的杂环基取代的二氢喹唑啉，以及它们的制备方法、含有它们的药物，以及用于治疗和/或预防疾病的方法，特别是作为抗病毒剂，特别是针对巨细胞病毒。
• Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs
  作者：Monroe E. Wall、Mansukh C. Wani、Allan W. Nicholas、Govindarajan Manikumar、Chhagan Tele、Linda Moore、Anne Truesdale、Peter Leitner、Jeffrey M. Besterman

  DOI：10.1021/jm00070a013

  日期：1993.9

  A large number of camptothecin (CPT) analogs have been prepared in the 20S, 20RS, and 20R configurations with a number of ring A substituents. Topoisomerase I (T-I) inhibition data (IC50) have been obtained by standard procedures. In general, substitution at the 9 or 10 positions with amino, halogeno, or hydroxyl groups in compounds with 20S configuration results in compounds with enhanced T-I inhibition

  已经制备了具有许多环A取代基的20S，20RS和20R构型的大量喜树碱（CPT）类似物。拓扑异构酶I（TI）抑制数据（IC50）已通过标准程序获得。通常，具有20S构型的化合物在9或10位上被氨基，卤代或羟基取代会导致TI抑制作用增强。20RS构型的化合物在体外和体内活性较低，而20R构型的化合物则无活性。在TI抑制试验中，在A环上具有10,11-亚甲二氧基取代的化合物显示出显着的效能增强。在包括L-1210小鼠白血病测定法在内的各种体内测定法中确定的某些类似物的活性通常与TI抑制作用一致。制备了许多水溶性类似物，例如20-甘氨酸酯，9-甘氨酰胺或水解的内酯盐，并在体外和体内试验中进行了测试。通常，就L-1210分析中的TI抑制作用和寿命延长而言，这些化合物的活性均不如CPT。然而，某些20-甘氨酸酯在静脉内给药后显示出良好的体内活性。
• Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction
  作者：Qiang Cheng、Jia‐Hao Xie、Yue‐Cheng Weng、Shu‐Li You

  DOI：10.1002/anie.201901251

  日期：2019.4.16

  Dearomatization of anthranils with vinylcyclopropanes (VCPs) by Pd‐catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand (L5), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes

  通过Pd催化的[4 + 3]环化反应实现了乙烯基环丙烷（VCP）对蒽的脱芳香化作用。在催化量的硼烷作为活化剂的存在下，以良好的至优异的产率和优异的立体选择性获得桥接的环状产物。通过引入手性PHOX配体（L5），蒽与乙烯基环丙烷的不对称脱芳香化反应以优异的对映选择性进行。硼烷在反应性中起关键作用，这可能是由于硼烷-蒽环配合物的形成，这已被NMR实验证实。