6-氟吲哚-3-乙腈 | 2341-25-5

• 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-3-乙腈
• 英文名称: 2-(6-fluoro-1H-indol-3-yl)acetonitrile
• CAS: 2341-25-5
• 化学式: C₁₀H₇FN₂
• mdl: MFCD09756481
• 分子量: 174.177
• InChiKey: PLNHDPOPGAMJAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Fluoroindole-3-acetonitrile
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-3-acetonitrile
CAS number: 2341-25-5

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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: C10H7FN2
Molecular weight: 174.2

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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：

  6-氟吲哚-3-乙腈 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 6-氟代吲哚-3-乙酸
  参考文献：
  名称：

  阴离子型相转移催化剂对吲哚衍生物的不对称脱芳香氟代酰胺化反应。

  摘要：

  使用二羧酸酯相转移催化剂研究了吲哚衍生物的不对称脱芳烃氟环化反应。该反应在温和的反应条件下进行，以高度对映选择性的方式提供氟吡咯并吲哚啉衍生物。吲哚环上的各种取代方式都具有良好的耐受性。为了促进反应并确保可重复性，必须添加水，并讨论其可能的作用。

  DOI：

  10.1021/acs.orglett.0c02026
• 作为产物：
  描述：

  3-fluoro-isonitrosoacetanilide 在 dimethylsulfide borane complex 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 6-氟吲哚-3-乙腈
  参考文献：
  名称：

  [EN] A NOVEL PROCESS FOR THE PREPARATION OF TRYPTAMINES AND DERIVATIVES THEREOF
  [FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE TRYPTAMINES ET DE LEURS DÉRIVÉS

  摘要：

  本发明涉及一种用于制备色胺、其取代衍生物和用于制备它们的中间体的新工艺。

  公开号：

  WO2017067670A1

文献信息

• [EN] NEW DERIVATIVES OF INDOLE FOR THE TREATMENT OF CANCER, VIRAL INFECTIONS AND LUNG DISEASES<br/>[FR] NOUVEAUX DÉRIVÉS D'INDOLE UTILES DANS LE TRAITEMENT DU CANCER, DES INFECTIONS VIRALES ET DES MALADIES PULMONAIRES
  申请人：BIOKINESIS

  公开号：WO2014086964A1

  公开（公告）日：2014-06-12

  The present invention relates to a new class of indole derivatives, having a particular MKlp2 inhibition profile and useful as a therapeutic agent, in particular for the treatment of cancer, viral infections and lung diseases.

  本发明涉及一类新的吲哚衍生物，具有特定的MKlp2抑制剂作用，并可用作治疗剂，特别是用于癌症、病毒感染和肺部疾病的治疗。
• Discovery of 3-[(4,5,7-Trifluorobenzothiazol-2-yl)methyl]indole-<i>N</i>-acetic Acid (Lidorestat) and Congeners as Highly Potent and Selective Inhibitors of Aldose Reductase for Treatment of Chronic Diabetic Complications
  作者：Michael C. Van Zandt、Michael L. Jones、David E. Gunn、Leo S. Geraci、J. Howard Jones、Diane R. Sawicki、Janet Sredy、Jorge L. Jacot、A. Thomas DiCioccio、Tatiana Petrova、Andre Mitschler、Alberto D. Podjarny

  DOI：10.1021/jm0492094

  日期：2005.5.1

  Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective 3-[(benzothiazol-2-yl)methyl]indole-N-alkanoic acid aldose reductase inhibitors. The lead candidate, 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat, 9) inhibits aldose reductase with an IC(50) of 5 nM, while being 5400

  最近鉴定慢性糖尿病并发症的治疗方法的努力导致发现了一系列新型的高效和选择性的3-[（（苯并噻唑-2-基）甲基]吲哚-N-链烷酸醛糖还原酶抑制剂。主要候选化合物3-[（（4,5,7-三氟苯并噻唑-2-基）甲基]吲哚-N-乙酸（利多司他，9）抑制醛糖还原酶，IC（50）为5 nM，是5400倍对醛还原酶的活性较低，醛还原酶是一种与活性醛解毒有关的酶。在为期5天的STZ诱导的糖尿病大鼠模型中，它可降低神经和晶状体山梨糖醇的水平，ED（50）分别为1.9和4.5 mg / kg / d po。在3个月的糖尿病干预模型中（糖尿病1个月，随后2个月以5 mg / kg / d po进行药物治疗），相对于糖尿病对照，它可以使多元醇正常化，并减少运动神经传导速度不足59％。它具有良好的药代动力学特征（F，82％; t（1/2），5.6 h; Vd，0.694 L / kg），并且在目标组织中的良好药物渗透
• Stereoselective Cascade Cyclizations with Samarium Diiodide to Tetracyclic Indolines: Precursors of Fluorostrychnines and Brucine
  作者：Christine Beemelmanns、Dominik Nitsch、Christoph Bentz、Hans‐Ulrich Reissig

  DOI：10.1002/chem.201900087

  日期：——

  stereoselectively provided a pentacyclic compound that was subsequently N‐protected and subjected to a regioselective elimination. The obtained functionalized pentacyclic product should be convertible into the alkaloid brucine by four well‐established steps. Overall, the presented report shows that functionalized tetracyclic compounds with different substituents are rapidly available with the samarium

  制备了一系列在苯部分带有氟，氰基或烷氧基取代基的γ-吲哚基酮，并进行了二碘化sa促进的环化反应。在所有情况下，以高非对映选择性，但产物分布不同进行所需的形成两个新环的脱芳香基酮基级联反应。在大多数情况下，所需的环状四环化合物以中等至良好的收率获得，但作为第二种产品，以高达29％的收率分离出四环螺内酯。反应速度受底物苯部分取代基的影响，受电子基团加速，给电子基团加速环化过程。在二氟取代的γ-吲哚基酮的情况下，观察到部分脱氟。四环产物的中间烯醇mar可通过添加反应性烷基化剂作为亲电子试剂来捕获，该亲电试剂传递具有季碳原子的产物。在二甲氧基取代的四环环化产物的情况下，随后的还原胺化反应选择性地立体提供了五环化合物，随后对其进行了N保护并进行了区域选择性消除。所获得的功能化五环产物应通过四个公认的步骤转化为生物碱马钱子碱。总体而言，本报告显示，具有不同取代基的功能化四环化合物可快速获得，其中碘化s
• [EN] FUSED BICYCLIC COMPOUNDS FOR THE TREATMENT OF DISEASE<br/>[FR] COMPOSÉS BICYCLIQUES FUSIONNÉS POUR LE TRAITEMENT DE MALADIES
  申请人：AKARNA THERAPEUTICS LTD

  公开号：WO2016151403A1

  公开（公告）日：2016-09-29

  Described herein are fused bicyclic compounds, compositions, and methods for their use for the treatment of disease.

  本文描述了融合的双环化合物、组合物以及它们用于治疗疾病的方法。
• [EN] 1,2,3,6-TETRAHYDROAZEPINO[4,5-B]INDOLE-5-CARBOXYLATE NUCLEAR RECEPTOR INHIBITORS<br/>[FR] INHIBITEURS DES RÉCEPTEURS NUCLÉAIRES DE 1,2,3,6-TÉTRAHYDROAZÉPINO[4,5-B]INDOLE-5-CARBOXYLATE
  申请人：WYETH CORP

  公开号：WO2010036362A1

  公开（公告）日：2010-04-01

  Provided are certain 1,2,3,6- tetrahydroazepino[4,5-b]indole-5-carboxylate compounds which are useful for modulating the activity of nuclear receptors, such as farnesoid X receptors, and/or for the treatment, prevention, or amelioration diseases or disorders related to the activity of these receptors.

  提供了一些1,2,3,6-四氢噁二氮杂并[4,5-b]吲哚-5-羧酸酯化合物，这些化合物对调节核受体的活性（如法尼索X受体）非常有用，或者用于治疗、预防或改善与这些受体活性相关的疾病或疾病。