6-氟吲哚-2-羧酸 | 3093-97-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 6-氟吲哚-2-羧酸
• 中文别名: 6-氟吲哚-2-甲酸
• 英文名称: 6-fluoro-1H-indole-2-carboxylic acid
• 英文别名: 6-fluoroindole-2-carboxylic acid
• CAS: 3093-97-8
• 化学式: C₉H₆FNO₂
• mdl: MFCD01863162
• 分子量: 179.151
• InChiKey: LRTIKMXIKAOCDM-UHFFFAOYSA-N

物化性质

• 熔点：
  246 °C (decomp)
• 沸点：
  422.2±25.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S43,S7/8
• 危险类别码：
  R10
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Fluoroindole-2-carboxylic acid
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: 6-Fluoroindole-2-carboxylic acid
CAS number: 3093-97-8

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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: C9H6FNO2
Molecular weight: 179.1

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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

6-氟吲哚-2-羧酸可以作为有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程。

反应信息

• 作为反应物：
  描述：

  6-氟吲哚-2-羧酸 在 N-甲基吡咯烷酮 、 铜 作用下， 以 乙醚 为溶剂， 反应 11.0h， 生成 N,N-diethyl-6-fluoroindol-3-ylglyoxalylamide
  参考文献：
  名称：

  Effect of Ring Fluorination on the Pharmacology of Hallucinogenic Tryptamines

  摘要：

  A series of fluorinated analogues of the hallucinogenic tryptamines N,N-diethyltryptamine (DET), 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT, psilocin), and 5-methoxy-DMT was synthesized to investigate possible explanations for the inactivity of 6-fluoro-DET as a hallucinogen and to determine the effects of fluorination on the molecular recognition and activation of these compounds at serotonin receptor subtypes. The target compounds were evaluated using in vivo behavioral assays for hallucinogen-like and 6-HT1A agonist activity and in vitro radioligand competition assays for their affinity at 5-HT2A, 5-HT2C, and 5-HT1A receptor sites. Functional activity at the 5-HT2A receptor was determined for all compounds. In addition, for some compounds functional activity was determined at the 5-HT1A receptor. Hallucinogen-like activity, evaluated in the two-lever drug discrimination paradigm using LSD-trained rats, was attenuated or abolished for all of the fluorinated analogues. One of the tryptamines, 4-fluoro-5-methoxy-DMT (6), displayed high 5-HT1A agonist activity, with potency greater than that of the 5-HT1A agonist 8-OH-DPAT. The ED50 Of 6 in the two-lever drug discrimination paradigm using rats trained to discriminate the 5-HT1A agonist LY293284 was 0.17 mu mol/kg, and the K-i at [H-3] 8-OH-DPAT-labeled 5-HT1A receptors was 0.23 nM. The results indicate that fluorination of hallucinogenic tryptamines generally has little effect on 5-HT2A/2C receptor affinity or intrinsic activity. Affinity at the 5-HT1A receptor was reduced, however, in all but one example, and all of the compounds tested were full agonists but with reduced functional potency at this serotonin receptor subtype. The one notable exception was 4-fluoro-5-methoxy-DMT (6), which had markedly enhanced 5-HT1A receptor affinity and functional potency. Although it is generally considered that hallucinogenic activity results from 5-HT2A receptor activation, the present results suggest a possible role for involvement of the 5-HT1A receptor with tryptamines.

  DOI：

  10.1021/jm000339w
• 作为产物：
  描述：

  6-氟-1H-吲哚-2-羧酸甲酯 在 sodium hydroxide 作用下， 反应 2.5h， 以99%的产率得到6-氟吲哚-2-羧酸
  参考文献：
  名称：

  Synthesis and structure of fluoroindole nucleosides

  摘要：

  化学修饰碱基常用于稳定核酸、研究核酸结构形成的驱动力以及调整 DNA 和 RNA 杂交条件。核苷类似物是研究氢键、碱基堆积和溶解这三种导致核酸稳定性的主要作用力的化学手段。为了更深入地了解这些相互作用对 RNA 稳定性的贡献，我们决定合成一些新型核酸类似物，用氟化吲哚取代核碱基。氟化吲哚可与氟化苯并咪唑进行比较，以确定氮在五元环系统中的作用。本文报告了氟吲哚核糖核苷的合成以及所有合成的氟吲哚核糖核苷的 X 射线晶体结构。这些化合物也可能成为多种具有生物活性的 RNA 类似物的构建基块。

  DOI：

  10.1139/v07-020

文献信息

• Copper-Mediated Cascade C–H/N–H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids
  作者：Ting-Yu Zhang、Chang Liu、Chao Chen、Jian-Xin Liu、Heng-Ye Xiang、Wei Jiang、Tong-Mei Ding、Shu-Yu Zhang

  DOI：10.1021/acs.orglett.7b03580

  日期：2018.1.5

  An efficient and environmentally benign Cu-mediated method was developed for direct cascade C–H/N–H annulation to construct polyheterocyclic indoloquinoline scaffolds. This method highlights an emerging strategy for transforming inert C–H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline

  开发了一种高效且环境友好的铜介导的方法，用于直接级联C–H / N–H环化，以构建多杂环吲哚并喹啉支架。该方法突出了在有机合成中将惰性C–H键转变为通用官能团的新兴策略，并为有效合成吲哚[3,2- c ]和[2,3- c ]喹啉生物碱提供了新的通用方法。
• [EN] PYRAZOLOSPIROKETONE ACETYL-C0A CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PYRAZOLOSPIROCÉTONE ACÉTL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2009144554A1

  公开（公告）日：2009-12-03

  The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供了式(1)的化合物或所述化合物的药用可接受盐，其中R1、R2和R3如本文所述；其药物组合物；以及用于治疗通过抑制动物中的乙酰辅酶A羧化酶酶活性来调节的疾病、病症或障碍的使用方法。
• [EN] SUBSTITUTED TRICYCLIC AMIDES, ANALOGUES THEREOF, AND METHODS USING SAME<br/>[FR] AMIDES TRICYCLIQUES SUBSTITUÉS, ANALOGUES DE CEUX-CI ET PROCÉDÉS LES METTANT EN OEUVRE
  申请人：ARBUTUS BIOPHARMA CORP

  公开号：WO2021229302A1

  公开（公告）日：2021-11-18

  The present disclosure includes substituted tricyclic amides, or analogues thereof of formula (I) (I), wherein X, Y, ring A, R1, R5, R6 and R7 are as defined herein, and compositions comprising compounds of formula (I) that can be used to treat or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient.

  本公开涵盖了替代三环酰胺，或其类似物的化合物，其化学式为(I)，其中X、Y、环A、R1、R5、R6和R7如本文所定义，并包括化合物(I)的组合物，可用于治疗或预防患者体内的乙型肝炎病毒（HBV）和/或丙型肝炎病毒（HDV）感染。
• [EN] FUSED RING PYRIMIDONE DERIVATIVES FOR USE IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES<br/>[FR] DÉRIVÉS DE PYRIMIDONE À CYCLES FUSIONNÉS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B OU DE MALADIES INDUITES PAR LE VIRUS DE L'HÉPATITE B
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2020182990A1

  公开（公告）日：2020-09-17

  The present application relates to compounds according to Formula (I), pharmaceutical compositions comprising at least one of said compounds, their use as a medicament, and their use in treating chronic hepatitis B virus (HBV) infection. The disclosure further pertains to methods for preparing compounds according to Formula (I).

  本申请涉及按照式(I)的化合物，包括至少一种所述化合物的药物组合物，其作为药物的用途，以及其在治疗慢性乙型肝炎病毒（HBV）感染中的用途。该公开还涉及按照式(I)制备化合物的方法。
• [EN] SUBSTITUTED (PHTHALAZIN-1-YLMETHYL)UREAS, SUBSTITUTED N-(PHTHALAZIN-1-YLMETHYL)AMIDES, AND ANALOGUES THEREOF<br/>[FR] (PHTALAZIN-1-YLMÉTHYL)URÉES SUBSTITUÉES, N- (PHTALAZIN-1-YLMÉTHYL)AMIDES SUBSTITUÉS ET ANALOGUES DE CEUX-CI
  申请人：ARBUTUS BIOPHARMA CORP

  公开号：WO2021250466A1

  公开（公告）日：2021-12-16

  The present disclosure includes certain substituted (phthalazin-1-ylmethyl)ureas, N- (phthalazin-1-ylmethyl)amides, and analogues thereof, and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient.

  本公开包括某些取代的(酞azine-1-ylmethyl)脲、N-(酞azine-1-ylmethyl)酰胺及其类似物，以及包含相同成分的组合物，可用于治疗或预防患者乙型肝炎病毒(HBV)和/或丁型肝炎病毒(HDV)感染。