4-溴-1,3-二氢-1-甲基-2H-吲哚-2-酮 | 884855-68-9

• 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: 4-溴-1,3-二氢-1-甲基-2H-吲哚-2-酮
• 中文别名: 4-溴-1-甲基吲哚啉-2-酮
• 英文名称: 4-bromo-1-methylindolin-2-one
• 英文别名: 4-bromo-1-methyl-3H-indol-2-one
• CAS: 884855-68-9
• 化学式: C₉H₈BrNO
• 分子量: 226.073
• InChiKey: YYTXVBYHPIORNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P280,P305+P351+P338
• 危险品运输编号：
  2811
• 危险性描述：
  H301

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-1-methylindolin-2-one
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: 4-Bromo-1-methylindolin-2-one
CAS number: 884855-68-9

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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: C9H8BrNO
Molecular weight: 226.1

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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 bromide.

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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：

  4-溴-1,3-二氢-1-甲基-2H-吲哚-2-酮 在 正丁基锂 、 sodium methylate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 43.0h， 生成 tert-butyl 5-(4-bromo-1-methyl-2,3-dihydro-2-oxindol-3-yl)-5-methyl-3-oxohexanoate
  参考文献：
  名称：

  welwitindolinones 的研究：N-methylwelwitindolinone C 异硫氰酸酯和相关天然产物的正式合成

  摘要：

  正式合成Ñ -methylwelwitindolinoneÇ异硫氰酸酯（4）等几个welwitindolinones 5 - 8分别通过独立合成实现79。该合成以路易斯酸介导的杂芳基甲醇和双-TMS 烯醇醚之间的偶联、分子内烯醇芳基化和前所未有的 γ-酰氧烯酮分子内烯丙基烷基化为特征。

  DOI：

  10.1016/j.tet.2013.03.010
• 作为产物：
  描述：

  4-溴-1-甲基吲哚-2,3-二酮 在 一水合肼 作用下， 反应 3.0h， 生成 4-溴-1,3-二氢-1-甲基-2H-吲哚-2-酮
  参考文献：
  名称：

  3-Carboxamide oxindoles 作为 1,3-C,N-双亲核试剂，用于高度非对映选择性合成含有 CF3 的螺-δ-内酰胺 oxindoles，在螺碳原子的邻位具有酰基

  摘要：

  通过3-羧酰胺羟吲哚和α,β-不饱和三氟甲基酮的Michael/ N-半缩酮化级联反应，建立了一种简单有效的合成δ-内酰胺稠合羟吲哚的策略。在温和的条件下，以中等至良好的收率和优异的非对映选择性获得了多种结构新颖的含有CF 3的螺-δ-内酰胺羟吲哚，其特征是在螺碳原子的邻位具有酰基。这项工作代表了系统研究 3-羧酰胺羟吲哚作为 1,3-C,N 双亲核试剂的第一个例子。

  DOI：

  10.1016/j.tetlet.2021.153426

文献信息

• Acylation of oxindoles using methyl/phenyl esters <i>via</i> the mixed Claisen condensation – an access to 3-alkylideneoxindoles
  作者：Ramdas Sreedharan、Purushothaman Rajeshwaran、Pradeep Kumar Reddy Panyam、Saurabh Yadav、C. M. Nagaraja、Thirumanavelan Gandhi

  DOI：10.1039/d0ob00789g

  日期：——

  Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources, viz. methyl and phenyl esters, which acylate oxindoles via the mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of

  在酰化过程中，主要使用侵蚀性的酰氯和化学计量的偶联剂来合成羰基束缚的杂环。在这里，我们报告简单的酰基来源，即。甲酯和苯酯，它们通过混合的克莱森缩合反应酰化吲哚。这种简单的方法是由LiHMDS和KOtBu介导的，并成功地应用于各种基材。这是一个值得注意的转变，它跳过了烯醇化物和酰化的逐步生成，并且该反应在中等温度下进行，没有任何副反应。该方案产生了芳基环中的邻位取代基的第一个例子，该芳基环上有供电子和吸电子底物。有趣的是，坚固的有机金属二茂铁基甲基酯在这些条件下容易裂解。此外，
• Direct One-Pot Synthesis of Naphthoxindoles from 4-Bromooxindoles by Suzuki-Miyaura Coupling and Aldol Condensation Reactions
  作者：Kyeong-Yong Park、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1002/ejoc.201301242

  日期：2014.1

  An efficient one-pot synthesis of naphthoxindoles by using 4-bromoindolin-2-ones and 2-formylphenylboronic acids has been developed. The coupling reaction proceeds in good to excellent yields under microwave irradiation through a Suzuki–Miyaura coupling and an aldol condensation cascade reaction. In addition, this protocol permits the facile construction of naphthoxindoles through an expanded scope

  使用 4-bromoindolin-2-ones 和 2-formylphenylboronic 酸有效地一锅合成萘并吲哚。在微波辐射下，通过 Suzuki-Miyaura 偶联和醇醛缩合级联反应，偶联反应以良好的产率进行。此外，该协议允许通过扩大的底物范围轻松构建萘并吲哚。
• Proline-Catalyzed Cyclization Reaction for the Synthesis of Naphthostyrils: Application to the Total Synthesis of Prioline
  作者：Kyeong-Yong Park、Ha-Jeong Song、Jung-Nyoung Heo

  DOI：10.1002/adsc.201500367

  日期：2015.10.12

  A new method for the synthesis of naphthostyrils is described. In this method, a sequential Stille coupling and proline-catalyzed cyclization procedure is employed for the reaction of 4-bromooxindoles and β-tributylstannyl-α,β-unsaturated ketones. The utility of this methodology is demonstrated in the first total synthesis of prioline from a simple 2-isopropylphenol.

  描述了一种合成萘并苯乙烯的新方法。在这种方法中，顺序的Stille偶联和脯氨酸催化的环化过程用于4-溴代吲哚和β-三丁基锡烷基-α，β-不饱和酮的反应。该方法的实用性在从简单的2-异丙基苯酚进行的第一个全合成吡咯啉中得到了证明。
• THERAPEUTIC COMPOUNDS
  申请人：Gilead Sciences, Inc.

  公开号：US20130281433A1

  公开（公告）日：2013-10-24

  Compounds disclosed herein including compounds of formula I′: and salts thereof are provided. Pharmaceutical compositions comprising compounds disclosed herein, processes for preparing compounds disclosed herein, intermediates useful for preparing compounds disclosed herein and therapeutic methods for treating an HIV infection using compounds disclosed herein are also provided.

  本文披露的化合物包括公式I′的化合物及其盐。还提供了包含本文披露的化合物的药物组合物、制备本文披露的化合物的方法、用于制备本文披露的化合物的中间体以及使用本文披露的化合物治疗HIV感染的治疗方法。
• [EN] INDAZOLYL THIADIAZOLAMINES AND RELATED COMPOUNDS FOR INHIBITION OF RHO-ASSOCIATED PROTEIN KINASE AND THE TREATMENT OF DISEASE<br/>[FR] THIADIAZOLAMINES INDAZOLYLE ET COMPOSÉS APPARENTÉS POUR L'INHIBITION DE PROTÉINE KINASE ASSOCIÉE À RHO ET LE TRAITEMENT DE MALADIES
  申请人：LYCERA CORP

  公开号：WO2016138335A1

  公开（公告）日：2016-09-01

  The invention provides indazolyl thiadiazolamines and related compounds, pharmaceutical compositions, methods of inhibiting Rho-associated protein kinase, and methods of treating inflammatory disorders, immune disorders, fibrotic disorders, and other medical disorders using such compounds. An exemplary indazolyl thiadiazolamine compound is an N-(5-[5-[(1H4ndazol-5-yl)amino]-1,3,4-thiadiazol-2-yl]pyridin-3-yl)acetamide compound.

  这项发明提供了吲唑基噻二唑胺及相关化合物、药物组合物、抑制Rho相关蛋白激酶的方法，以及利用这些化合物治疗炎症性疾病、免疫性疾病、纤维化疾病和其他医学疾病的方法。一种示例性的吲唑基噻二唑胺化合物是N-(5-[5-[(1H-吲唑-5-基)氨基]-1,3,4-噻二唑-2-基]吡啶-3-基)乙酰胺化合物。