5-羧酸甲酯二氢吲哚-2-酮 | 199328-10-4

• 物质功能分类: 医药中间体 - 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: 5-羧酸甲酯二氢吲哚-2-酮
• 中文别名: 2-氧代吲哚-5-甲酸甲酯
• 英文名称: methyl 2-oxoindoline-5-carboxylate
• 英文别名: methyl 2-oxo-2,3-dihydro-1H-indole-5-carboxylate；5-methoxycarbonyl-2-indolinone；Methyl Oxindole-5-carboxylate；methyl 2-oxo-1,3-dihydroindole-5-carboxylate
• CAS: 199328-10-4
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: CYBPPDZFRDSSME-UHFFFAOYSA-N

物化性质

• 熔点：
  192-199
• 沸点：
  405.6±45.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2933790090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl oxindole-5-carboxylate
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: Methyl oxindole-5-carboxylate
CAS number: 199328-10-4

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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.
Store in closed vessels.
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: C10H9NO3
Molecular weight: 191.2

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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.

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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

5-羧酸甲酯二氢吲哚-2-酮可用作有机合成中间体和医药中间体，主要用于实验室研发过程和化工生产过程中。

制备此化合物的方法如下：在大气压的一氧化碳饱和条件下，将17克5-碘代-2-羟基吲哚与2克二乙酸钯、18.2克三乙胺、150毫升甲醇、15毫升二甲基亚砜以及2.6克DPPP一起回流。反应24小时后，过滤除去催化剂并浓缩滤液。将浓缩物使用30%的乙酸乙酯在己烷中进行层析，收集含有目标产物的部分并进一步浓缩和放置。最后，产物通过真空过滤收集，得到0.8克（产率7%）灰白色固体的5-羧酸甲酯二氢吲哚-2-酮。

反应信息

• 作为反应物：
  描述：

  5-羧酸甲酯二氢吲哚-2-酮 在 盐酸 作用下， 以 水 为溶剂， 以97%的产率得到5-羧基吲哚-2-酮
  参考文献：
  名称：

  [EN] SELECTIVE HDAC3 INHIBITORS
  [FR] INHIBITEURS HDAC3 SÉLECTIFS

  摘要：

  本文提供了HDAC3抑制剂，以及包括将这些化合物用于需要的受试者的治疗方法。

  公开号：

  WO2014121062A1
• 作为产物：
  描述：

  5-碘吲哚-2-酮 在 palladium diacetate 三乙胺 作用下， 以 甲醇 、 正己烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 以0.8 g (7%)的产率得到5-羧酸甲酯二氢吲哚-2-酮
  参考文献：
  名称：

  Indolinone combinatorial libraries and related products and methods for

  摘要：

  本发明涉及能够调节、调控和/或抑制蛋白激酶信号传导的有机分子。这些化合物对于治疗与未调节的蛋白激酶信号传导相关的疾病非常有用，包括细胞增殖性疾病，如癌症、动脉粥样硬化、关节炎和再狭窄，以及代谢性疾病，如糖尿病。本发明涵盖了强力抑制蛋白激酶及相关产品和方法的吲哚酮化合物。通过向3-[(吲哚-3-基)甲烷基]-2-吲哚酮，特别是在吲哚环的1'位置添加化学取代基，可以获得特异于FLK蛋白激酶的抑制剂。具有特异抑制FLK和血小板源性生长因子蛋白激酶的吲哚酮化合物可以含有四氢吲哚或环戊基-β-吡咯基。在氧吲哚环的5位取代基上进行修饰的吲哚酮化合物可以有效激活蛋白激酶。本发明还涉及一种新型的亲水性吲哚酮化合物，它们是酪氨酸激酶抑制剂及相关产品和方法。

  公开号：

  US06147106A1

文献信息

• NOVEL CYCLOPROPANE INDOLINONE DERIVATIVES
  申请人：Chen Li

  公开号：US20110144106A1

  公开（公告）日：2011-06-16

  The present invention relates to a compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R 1 to R 4 have the significance given in claim 1 . The compound may be used, for example, for the treatment or prophylaxis of obesity, hyperglycemia, dyslipidemia, and type 1 or type 2 diabetes,

  本发明涉及一种具有化学式（I）的化合物，以及其药学上可接受的盐，其中R1至R4具有权利要求1中给定的含义。该化合物可以用于治疗或预防肥胖、高血糖、血脂异常以及1型或2型糖尿病。
• 3-heteroarylidene-2-indolinone protein kinase inhibitors
  申请人：Sugen, Inc.

  公开号：US06486185B1

  公开（公告）日：2002-11-26

  The present invention relates to novel 3-heteroarylidene-2-indolinone compounds and physiologically acceptable salts thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及新颖的3-杂环亚烯基-2-吲哚酮化合物及其生理上可接受的盐，这些化合物调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用处。
• Formulations for pharmaceutical agents ionizable as free acids or free bases
  申请人：Shenoy Narmada

  公开号：US06878733B1

  公开（公告）日：2005-04-12

  The present invention features formulations of indolinones which compounds are ionizable as free acids or free bases. The formulation is suitable for parenteral or oral administration, wherein the formulation comprises an ionizable substituted indolinone, and a pharmaceutically acceptable carrier therefor. The term “ionizable substituted indolinone” includes pyrrole substituted 2-indolinones which, in addition to being otherwise optionally substituted on both the pyrrole and 2-indolinone portions of the compound, are necessarily substituted on the pyrrole moiety with one or more hydrocarbon chains which themselves are substituted with at least one polar group. The formulations and the compounds themselves are useful for the treatment of protein kinase related disorders as discussed herein.

  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。
• 3-(cycloalkanoheteroarylidenyl)-2-indolinone protein tyrosine kinase inhibitors
  申请人：Sugen, Inc.

  公开号：US06350754B2

  公开（公告）日：2002-02-26

  The present invention relates to novel 3-(cycloalkano-heteroarylidenyl)-2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which are expected to modulate the activity of protein tyrosine kinases and therefore to be useful in the prevention and treatment of protein tyrosine kinase related cellular disorders such as cancer.

  本发明涉及新颖的3-(环烷基-杂环芳基亚亚甲基)-2-吲哚酮化合物及其生理上可接受的盐和前药，预计这些化合物可以调节蛋白酪氨酸激酶的活性，因此在预防和治疗蛋白酪氨酸激酶相关的细胞疾病，如癌症方面具有用处。
• [EN] SPIRO INDOLE - CYCLOPROPANE INDOLINONES USEFUL AS AMPK MODULATORS<br/>[FR] SPIRO-INDOLE-CYCLOPROPANE-INDOLINONES UTILES EN TANT QUE MODULATEURS D'AMPK
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011070039A1

  公开（公告）日：2011-06-16

  A compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R1 to R4 have the significance given in claim 1, can be used as a modulator of AMPK.

  化合物的化学式（I）及其药用盐，其中R1至R4具有权利要求1中给定的含义，可用作AMPK的调节剂。