4-氟-3-硝基苯甲醚 | 61324-93-4

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 4-氟-3-硝基苯甲醚
• 中文别名: 3-硝基-4-氟苯甲醚
• 英文名称: 1-fluoro-4-methoxy-2-nitrobenzene
• 英文别名: 4-fluoro-3-nitroanisole；4-methoxy-1-fluoro-2-nitrobenzene；1-fluoro-nitro-4-methoxybenzene
• CAS: 61324-93-4
• 化学式: C₇H₆FNO₃
• 分子量: 171.128
• InChiKey: ZRIKJXDEJYMBEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  279.5±20.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2909309090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  室温和干燥环境

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Fluoro-3-nitroanisole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Fluoro-3-nitroanisole
CAS number: 61324-93-4

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H6FNO3
Molecular weight: 171.1

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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

制备方法与用途

简介

4-氟-3-硝基苯甲醚是一种醚类有机物，可通过将4-氟-3-硝基苯酚与碘甲烷进行烷基化反应制得。

用途

4-氟-3-硝基苯甲醚主要用于合成医药中间体。据文献报道，它可用于制备RIPK1抑制剂，而RIPK1激酶在TNF-α诱导的细胞死亡过程中起着关键作用。

制备方法

将4-氟-3-硝基苯酚（3.14 g）溶解于丙酮（40 ml）中。随后向溶液中加入甲基碘（5.68 g）和碳酸钾（5.53 g），在40℃下搅拌6小时。然后，加入二氯甲烷（50 ml）并过滤除去不溶性物质。滤液减压浓缩后，残余物用乙酸乙酯（50 ml）溶解。接着依次用水、1N氢氧化钠水溶液和盐水洗涤有机层，并用硫酸钠干燥，过滤。最后，通过减压浓缩得到4-氟-3-硝基苯甲醚（3.47 g），为棕色油状物。

反应信息

• 作为反应物：
  描述：

  4-氟-3-硝基苯甲醚 在 盐酸 、 铁粉 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 N-(2-氨基-4-甲氧基苯基)-n-甲基胺
  参考文献：
  名称：

  Cu催化苯并咪唑与艾伦的C-H烯丙基化

  摘要：

  已经描述了 CuH 催化的苯并咪唑与丙二烯的分子内环化和分子间烯丙基化。在Cu(OAc) 2 /Xantphos的催化体系和催化量的(MeO) 2 MeSiH的作用下，反应顺利进行。该协议具有温和的反应条件和对带有吸电子、给电子或电子中性基团的底物的良好耐受性。针对该氢化铜催化体系提出了一种新的催化机理。

  DOI：

  10.1021/acs.orglett.1c02346
• 作为产物：
  描述：

  2-甲氧基-4-硝基-5-氟苯胺 在 硫酸 、 sodium nitrite 、 sodium hypophosphite 作用下， 以 水 为溶剂， 以77 %的产率得到4-氟-3-硝基苯甲醚
  参考文献：
  名称：

  一种3-硝基-4-氟苯甲醚的制备方法

  摘要：

  本发明公开了一种3‑硝基‑4‑氟苯甲醚的制备方法，所述制备方法包括如下步骤：(1)化合物(II)与甲醇钠反应生成化合物(III)；(2)化合物(III)经还原反应生成化合物(IV)；(3)化合物(IV)与醋酸酐反应生成化合物(V)；(4)化合物(V)经浓硫酸、硝酸硝化生成化合物(VI)；(5)化合物(VI)脱乙酰基生成化合物(VII)；(6)化合物(VII)与亚硝酸钠生成重氮盐，在次亚磷酸钠条件下重氮盐脱氨基生成化合物(I)。本发明制备方法的产率更高。

  公开号：

  CN115417772A

文献信息

• [EN] INDAZOLE- AND PYRROLOPYRIDINE-DERIVATIVE AND PHARMACEUTICAL USE THEREOF<br/>[FR] DÉRIVÉ D'INDAZOLE ET PYRROLOPYRIDINE ET UTILISATION PHARMACEUTIQUE DE CELUI-CI
  申请人：DAINIPPON SUMITOMO PHARMA CO

  公开号：WO2012169649A1

  公开（公告）日：2012-12-13

  The present invention relates to a novel indazole- or pyrrolopyridine-derivative, represented by the formula (1) below, that has an agonistic action or a partial agonistic action against serotonin-4 receptor, and a pharmaceutical composition comprising the same. Formula (1) [wherein each substituent is as defined in claim 1]

  本发明涉及一种新型吲唑基或吡咯吡啶基衍生物，由下面的式（1）表示，该衍生物对5-羟色胺-4受体具有激动作用或部分激动作用，并且包括含有该衍生物的药物组合物。式（1）[其中每个取代基如权利要求1所定义]
• Electronic Effects on the cis/trans Selectivity in Formation of Isoxazolidine-Fused Eight-Membered Ring via an Intramolecular Nitrone-Alkene Cycloaddition
  作者：Jinbao Xiang、Tong Zhu、Qun Dang、Xu Bai

  DOI：10.1007/s10593-016-1938-z

  日期：2016.8

  electron density of the benzene ring had a significant effect on cis/trans selectivity. These reactions were useful for the synthesis of novel tricyclic hexahydrobenzo[b]isoxazolo[3,4-f][1, 4]diazocin-4(1H)-ones and hexahydroisoxazolo[3,4-f]pyrido[3,2-b][1, 4]diazocin-4(1H)-one under mild reaction conditions in good yields

  涉及原位产生的硝酮的分子内硝酮-烯烃环加成反应的反应曲线不同于先前报道的嘧啶体系。调整苯环的电子密度对顺/反式选择性有重要影响。这些反应可用于合成新型三环六氢苯并[ b ]异恶唑并[3,4- f ] [1，4]二唑-4（1 H）-ones和六氢异恶唑并[3,4- f ]吡啶[3,2 - b ] [1，4] diazocin-4（1 ħ） -酮以良好的收率下温和的反应条件
• Discovery and Characterization of Benzimidazole Derivative XY123 as a Potent, Selective, and Orally Available RORγ Inverse Agonist
  作者：Xishan Wu、Hui Shen、Yan Zhang、Chao Wang、Qiu Li、Cheng Zhang、Xiaoxi Zhuang、Chenchang Li、Yudan Shi、Yanli Xing、Qiuping Xiang、Jinxin Xu、Donghai Wu、Jinsong Liu、Yong Xu

  DOI：10.1021/acs.jmedchem.1c00763

  日期：2021.6.24

  (IC50) value of 64 nM and showed excellent selectivity against other nuclear receptors. 27h also potently suppressed cell proliferation, colony formation, and the expression of androgen receptor (AR)-regulated genes in AR-positive prostate cancer cell lines. In addition, 27h demonstrated good metabolic stability and a pharmacokinetic property with reasonable oral bioavailability (32.41%) and moderate half-life

  受体相关孤儿受体γ（RORγ）已成为治疗癌症和炎症性疾病的一个有吸引力的治疗靶点。在此，我们报告了我们在苯并噻唑和苯并咪唑衍生物作为 RORγ 新型反向激动剂的发现、优化和评估方面所做的努力。代表性化合物27h （命名为XY123）有效抑制RORγ转录活性，半数抑制浓度（IC 50 ）值为64 nM，并对其他核受体表现出优异的选择性。 27h还有效抑制 AR 阳性前列腺癌细胞系中的细胞增殖、集落形成和雄激素受体 (AR) 调节基因的表达。此外， 27h表现出良好的代谢稳定性和药代动力学特性，具有合理的口服生物利用度 (32.41%) 和中等的半衰期 ( t 1/2 = 4.98 h)。值得注意的是，口服化合物27h在小鼠22Rv1异种移植肿瘤模型中实现了完全且持久的肿瘤消退。化合物27h可能作为一种新的有价值的先导化合物，用于进一步开发治疗前列腺癌的药物。
• [EN] 5-(1 H-BENZO[D]IMIDAZO-2-YL)-PYRIDIN-2-AMINE AND 5-(3H-IMIDAZO[4,5-B]PYRIDIN-6-YL)-PYRIDIN-2-AMINE DERIVATIVES AS C-MYC AND P300/CBP HISTONE ACETYLTRANSFERASE INHIBITORS FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 5-(1 H-BENZO[D]IMIDAZO-2-YL)-PYRIDIN-2-AMINE ET DE 5-(3H-IMIDAZO[4,5-B]PYRIDIN-6-YL)-PYRIDIN-2-AMINE UTILISÉS EN TANT QU'INHIBITEURS D'HISTONE ACÉTYLTRANSFÉRASE DE C-MYC ET P300/CBP POUR LE TRAITEMENT DU CANCER
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2019049061A1

  公开（公告）日：2019-03-14

  The invention is directed to substituted 5-(1H-benzo[d]imidazo-2-yl)- pyridin-2-amine and 5-(3H-imidazo[4,5-b]pyridin-6-yl)-pyridin-2-amine derivatives. Specifically, the invention is directed to compounds according to Formula (lb) wherein R', R2', R3', R4', Rs', R6', R7', and X1' are as defined herein; or a salt thereof including a pharmaceutically acceptable salt thereof. The compounds of the invention decrease MYC protein (c-MYC) in cells and/or inhibit p300/CBP histone acetyltransferase and can be useful in the treatment of cardiac hypertrophy, diabetes, obesity & nonalcoholic fatty liver disease, HIV, polycystic kidney disease, inflammatory diseases, ankylosing spondylitis, psoriasis, psoriatic arthritis, rheumatoid arthritis, Crohn's disease, multiple sclerosis, cancer and pre-cancerous syndromes, and diseases associated with dysregulation of Myc or inhibition of p300/CBP histone acetyltransferase. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention still further discloses methods of reducing MYC protein (c-MYC) in cells and inhibiting p300/CBP histone acetyltransferase activity, and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代的5-(1H-苯并[d]咪唑-2-基)-吡啶-2-胺和5-(3H-咪唑[4,5-b]吡啶-6-基)-吡啶-2-胺衍生物。具体而言，本发明涉及根据公式(lb)的化合物，其中R'、R2'、R3'、R4'、Rs'、R6'、R7'和X1'按本说明书中定义；或其盐，包括药用可接受的盐。本发明的化合物能够降低细胞中的MYC蛋白（c-MYC）和/或抑制p300/CBP组蛋白乙酰转移酶，可用于治疗心肌肥大、糖尿病、肥胖和非酒精性脂肪肝疾病、HIV、多囊肾疾病、炎症性疾病、强直性脊柱炎、银屑病、银屑病关节炎、类风湿性关节炎、克罗恩病、多发性硬化症、癌症和前癌症综合症，以及与Myc失调或p300/CBP组蛋白乙酰转移酶抑制相关的疾病。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步公开了使用本发明的化合物或包含本发明化合物的药物组合物，降低细胞中MYC蛋白（c-MYC）和抑制p300/CBP组蛋白乙酰转移酶活性的方法，以及治疗与之相关的疾病的方法。
• Catalytic Enantioselective Michael Addition of α-Aryl-α-Isocyanoacetates to Vinyl Selenone: Synthesis of α,α-Disubstituted α-Amino Acids and (+)- and (−)-Trigonoliimine A
  作者：Thomas Buyck、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.201306663

  日期：2013.11.25

  title reaction in the presence of the catalyst 1 afforded Michael adducts in excellent yields and enantioselectivities. The adducts were readily converted into α,α′‐disubstituted α‐amino acids. The enantioselective total synthesis of both (+)‐ and (−)‐trigonoliimine A was accomplished using one of the Michael adducts derived from this methodology. M.S.=molecular sieves.

  就像迈克：在催化剂1的存在下进行标题反应，可以以出色的收率和对映选择性提供迈克尔加合物。加合物易于转化为α，α'-二取代的α-氨基酸。（+）-和（-）-三角果碱亚胺A的对映选择性全合成是使用衍生自该方法的迈克尔加合物之一完成的。MS ＝分子筛。