6-羟基吲哚啉-2-酮 | 6855-48-7

• 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-羟基吲哚啉-2-酮
• 中文别名: 6-羟基吲哚酮；1,3-二氢-6-羟基-2H-吲哚-2-酮；6-羟基吲哚-2-酮
• 英文名称: 6-Hydroxy-oxindol
• 英文别名: 6-hydroxyindolin-2-one；6-hydroxy oxindole；6-hydroxy-1,3-dihydroindol-2-one
• CAS: 6855-48-7
• 化学式: C₈H₇NO₂
• mdl: MFCD05663501
• 分子量: 149.149
• InChiKey: ZOJZYAPVVOLQQB-UHFFFAOYSA-N

物化性质

• 熔点：
  243 °C
• 沸点：
  396.3±42.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 6-Hydroxy-1,3-dihydro-indol-2-one
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 6-Hydroxy-1,3-dihydro-indol-2-one
CAS number: 6855-48-7

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C8H7NO2
Molecular weight: 149.1

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-羟基吲哚啉-2-酮 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(3,5-dimethylpyrrol-2-yl)methylidenyl]-6-(4-nitrobenzyloxy)indolin-2-one
  参考文献：
  名称：

  Synthesis and evaluation of prodrugs for anti-angiogenic pyrrolylmethylidenyl oxindoles

  摘要：

  Potential prodrugs of inhibitors of VEGF-induced angiogenesis have been investigated. The prodrug systems studied were the 4-nitrobenzyl, 2-nitrophenylacetyl and 3-methyl-3-(3,6-dimethylbenzo-1,4-quinon-2-yl)butanoyI groups, readily attached to acidic OH or NH groups in drug molecules, and released upon bioreductive activation. The anti-angiogenic compounds studied were the pyrrolylmethylidenyl oxindole SU5416 (semaxanib) and its novel 6-hydroxy derivative. The potentially pro-anti-angiogenic compounds were assayed for their ability to block VEGF-induced angiogenesis in HUVECS in comparison to the free agents. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.108
• 作为产物：
  描述：

  6-甲氧基-2-氧化吲哚 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到6-羟基吲哚啉-2-酮
  参考文献：
  名称：

  Formulations for pharmaceutical agents ionizable as free acids or free bases

  摘要：

  本发明涉及吲哚酮的配方，这些化合物作为游离酸或游离碱是可离子化的。该配方适用于静脉或口服给药，其中配方包括可离子化的取代吲哚酮和其药用可接受载体。术语“可离子化的取代吲哚酮”包括吡咯取代的2-吲哚酮，除了在化合物的吡咯和2-吲哚酮部分上可选择地被取代外，必须在吡咯基上用一个或多个烃链取代，这些烃链本身被至少一个极性基团取代。如本文所述，这些配方和化合物本身对于治疗蛋白激酶相关疾病是有用的。

  公开号：

  US06878733B1

文献信息

• [EN] AMINE-LINKED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION<br/>[FR] DÉGRONIMÈRES DE C3-GLUTARIMIDE LIÉS À UNE AMINE POUR LA DÉGRADATION DE PROTÉINES CIBLES
  申请人：C4 THERAPEUTICS INC

  公开号：WO2017197051A1

  公开（公告）日：2017-11-16

  This invention provides amine-linked C3-glutarimide Degronimers and Degrons for therapeutic applications as described further herein, and methods of use and compositions thereof as well as methods for their preparation.

  这项发明提供了胺连接的C3-戊二酰亚胺Degronimers和Degrons，用于治疗应用，如本文进一步描述的，以及它们的使用方法、组合物以及它们的制备方法。
• [EN] HSD17B13 INHIBITORS AND USES THEREOF<br/>[FR] COMPOSÉS ET UTILISATIONS DE CEUX-CI
  申请人：INIPHARM INC

  公开号：WO2021211974A1

  公开（公告）日：2021-10-21

  Described herein are HSD17B13 inhibitors and pharmaceutical compositions comprising said inhibitors. The subject compounds and compositions are useful for the treatment of liver disease, metabolic disease, or cardiovascular disease, such as NAFLD or NASH, or drug induced liver injury (DILI).

  本发明涉及HSD17B13抑制剂及包含所述抑制剂的药物组合物。所述化合物和组合物可用于治疗肝病、代谢性疾病或心血管疾病，例如非酒精性脂肪肝病（NAFLD）或非酒精性脂肪肝炎（NASH），或药物诱导的肝损伤（DILI）。
• C5, C6 SUBSTITUTED AND/OR FUSED OXINDOLES AS ANTI-CANCER AGENTS AND PROCESS FOR PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：US20180127365A1

  公开（公告）日：2018-05-10

  The present invention describes the C5,C6 Substituted and/or fused oxindole compounds useful as anti-cancer agents and process for preparation thereof. Particularly the present invention relates to C5,C6 Substituted and/or fused oxindole compounds of formula I. wherein, A=C, CH, CH 2 , None B=C or CH part of open chain and/or cyclic alkyl/aryl/heteroaryl moiety G=alkyl, alkenyl, alkynyl, aryl, heteroaryl, heteroalkyl, alkoxy, aryloxy-all these optionally substituted with one or more substituents D=O, N, S, OH, SH, NH, None Z=C, CH 2 Ring E=aryl/heteroaryl/cycloalkyl optionally substituted with one or more substituents Ring C=aryl/heteroaryl/cycloalkyl optionally substituted with one or more substituents L=H, alkyl, alkoxy, halogen, CN, OH, amino, NO 2 K=H, alkyl, alkoxy, halogen, CN, OH, amino, NO 2 X=H, alkyl, alkoxy, halogen, CN, OH, amino, NO 2 Y=H, alkyl, alkoxy, halogen, CN, OH, amino, NO 2 R1=H, alkyl R2=H, alkyl, halogen, CN, NO 2 , alkoxy, amino, OH

  本发明描述了C5，C6取代和/或融合的噁嗪酮化合物，可用作抗癌剂，并描述了其制备方法。特别是本发明涉及公式I中的C5，C6取代和/或融合的噁嗪酮化合物，其中，A=C，CH，CH2，None；B=C或CH，部分为开链和/或环烷基/芳基/杂环烷基；G=烷基，烯基，炔基，芳基，杂芳基，杂烷基，烷氧基，芳氧基，这些都可以选择地被一个或多个取代基取代；D=O，N，S，OH，SH，NH，None；Z=C，CH2；环E=芳基/杂芳基/环烷基，可以选择地被一个或多个取代基取代；环C=芳基/杂芳基/环烷基，可以选择地被一个或多个取代基取代；L=H，烷基，烷氧基，卤素，CN，OH，氨基，NO2；K=H，烷基，烷氧基，卤素，CN，OH，氨基，NO2；X=H，烷基，烷氧基，卤素，CN，OH，氨基，NO2；Y=H，烷基，烷氧基，卤素，CN，OH，氨基，NO2；R1=H，烷基；R2=H，烷基，卤素，CN，NO2，烷氧基，氨基，OH。
• 3,3-dialkyl-and 3,3-alkylene-indoline derivatives, processes for their
  申请人：Sandoz Ltd.

  公开号：US04622336A1

  公开（公告）日：1986-11-11

  3,3-Dialkyl- or 3,3-alkylene-indolines which are unsubstituted at the 1- and 2-positions and which are substituted at the 4- or 6-position by an optionally etherified hydroxy group or substituted at the 5- or 7-position by an etherified hydroxy group, as well as their physiologically-hydrolyzable and -acceptable esters. The said indolines and esters as well as their pharmaceutically acceptable acid addition salts possess analgesic activity.

  3,3-二烷基-或3,3-烷基烯基-吲哚啉，其在1-和2-位置未取代，在4-或6-位置被一羟基可选地醚化取代，或在5-或7-位置被一醚化羟基取代，以及它们的生理可水解和可接受的酯。所述的吲哚啉和酯以及它们的药用可接受的酸盐具有镇痛活性。
• [EN] A SHORT PROCESS FOR THE PREPARATION OF ZIPRASIDONE AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ COURT POUR LA PRÉPARATION DE ZIPRASIDONE ET DE SES INTERMÉDIAIRES
  申请人：ARCH PHARMALABS LTD

  公开号：WO2012020424A1

  公开（公告）日：2012-02-16

  A process for the preparation of oxindole derivative (Ziprasidone hydrochloride) of formula (I) comprising reacting compound of formula (II) with metal or metal compound mineral acid to give compound of formula (III) in a single step which is converted into compound of formula IV which is a key intermediate for the preparation of compound of compound of formula (I).

  一种制备氧化吲哚衍生物（盐酸齐拉西酮）的方法，包括将式（II）的化合物与金属或金属化合物矿酸反应，以一步得到式（III）的化合物，该化合物转化为式IV的化合物，后者是制备式（I）的化合物的关键中间体。