4-氯-2-氧化吲哚 | 20870-77-3

• 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-氯-2-氧化吲哚
• 中文别名: 4-氯吲哚酮；4-氯-1,3-二氢吲哚-2-酮；4-氯-2-吲哚酮
• 英文名称: 4-chloroindolin-2-one
• 英文别名: 4-chloro-1,3-dihydroindol-2-one
• CAS: 20870-77-3
• 化学式: C₈H₆ClNO
• mdl: MFCD03787567
• 分子量: 167.595
• InChiKey: XNSPDJAXCBZCRV-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208°
• 沸点：
  340.3±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)：
  1.4
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Chlorooxindole
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-Chlorooxindole
CAS number: 20870-77-3

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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: C8H6ClNO
Molecular weight: 167.6

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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 chloride.

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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-氯-2-氧化吲哚 在 sodium borohydrid 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 4-氯吲哚啉
  参考文献：
  名称：

  .beta.-Lactam series compound and antibacterial pharmaceutical

  摘要：

  一种由化学式(I)表示的β-内酰胺系列化合物：##STR1##其中R^1代表氢原子或较低的烷基基团；R^2代表氢原子；R^3代表卤素原子、硝基基团、氨基基团、羟基基团、较低的烷基基团、较低的烷氧基基团、较低的烷酰胺基团、较低的烷磺酰氧基团或由化学式##STR2##表示的基团，其中R^5代表氢原子、较低的烷酰基团或较低的烷磺酰基团；R^4代表氢原子或羟基基团；n为0或1；l为0、1或2；A代表--C(CH_3)_2--CH(COOH)--或--CH_2C(CH_2R^6)=C(COOH)--，其中R^6代表较低的烷酰氧基团，由化学式##STR3##表示的基团，其中R^7和R^8各自代表较低的烷基团，当n为0时，R^1和R^2可以结合形成与它们连接的碳原子一起的环己烷环，并公开了其药学上可接受的盐以及制备同样的方法。这些化合物具有抗微生物活性。

  公开号：

  US04317820A1
• 作为产物：
  描述：

  2,3-二氯硝基苯 在 铁粉 、 sodium hydride 、 lithium chloride 作用下， 以 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 6.17h， 生成 4-氯-2-氧化吲哚
  参考文献：
  名称：

  A General Oxindole Synthesis

  摘要：

  一种针对吲哚-2(3H)-酮（氧吲哚）的整体合成方法被开发，该方法基于二甲基马来酸酯与可商业获得的卤代硝基苯的加成。这条路线相较于许多其他氧吲哚合成方法的优势在于对芳香环取代模式的区域化学控制。

  DOI：

  10.1055/s-1993-25790

文献信息

• Iron‐Catalyzed Direct Oxidative Alkylation and Hydroxylation of Indolin‐2‐ones with Alkyl‐Substituted N‐Heteroarenes
  作者：Ren‐Ming Hu、Dong‐Yang Han、Ning Li、Jie Huang、Yu Feng、Da‐Zhen Xu

  DOI：10.1002/anie.201913400

  日期：2020.3.2

  alkyl-substituted N-heteroarenes, through an oxidative cross-coupling reaction. The reaction is catalyzed by a simple iron salt under mild ligand-free and base-free conditions. The reaction is environmentally benign, employs air (molecular oxygen) as the terminal oxidant and oxygen source for the synthesis of O-containing compounds, and produces only water as the byproduct.

  本文提出的是两个不同的C（sp3）-H键，吲哚-2-酮和烷基取代的N-杂芳烃之间通过氧化交叉偶联反应的首次直接烷基化和羟基化反应。该反应由简单的铁盐在温和的无配体和无碱条件下催化。该反应在环境上是无害的，使用空气（分子氧）作为末端氧化剂和氧源来合成含O的化合物，仅产生水作为副产物。
• 一种苯并异硒唑酮修饰的吡咯甲酸酯取代的吲 哚酮类化合物及其应用
  申请人：北京大学

  公开号：CN102898402B

  公开（公告）日：2016-01-20

  本申请依赖并要求2011年4月26日提交的中国专利申请201110105248.0的优先权，在此通过参考将其全部内容并入本文。本发明涉及苯并异硒唑酮修饰的吡咯甲酸酯取代的吲哚酮类化合物及其应用。本发明的苯并异硒唑酮修饰的吡咯甲酸酯取代的吲哚酮类化合物如通式I所示。本发明的2-吲哚酮类化合物具有优良的抗肿瘤活性，可广泛用于制备抗肿瘤药物。通式I。
• Highly Enantioselective Synthesis of Spiro[cyclohexanone-oxindoles] and Spiro[cyclohexanone-pyrazolones] by Asymmetric Cascade [5+1] Double Michael Reactions
  作者：Bin Wu、Jian Chen、Mei-Qiu Li、Jin-Xin Zhang、Xiao-Ping Xu、Shun-Jun Ji、Xing-Wang Wang

  DOI：10.1002/ejoc.201101529

  日期：2012.3

  The asymmetric catalytic synthesis of naturally occurring and biologically active spiro compounds is a challenge for modern chemical methodology. Here we report the construction of spiro compounds through cascade [5+1] double Michael reactions between divinyl ketones and N-unprotectedoxindoles or N-phenyl-protected pyrazolones catalyzed by a combination of the easily available 9-amino-9-deoxy-epi-quinine

  天然存在和生物活性螺环化合物的不对称催化合成是现代化学方法的挑战。在这里，我们报告了通过二乙烯基酮和 N-未保护的羟吲哚或 N-苯基保护的吡唑啉酮之间的级联 [5+1] 双迈克尔反应构建螺环化合物，该反应由易于获得的 9-氨基-9-脱氧-表奎宁与 N-Boc-D-苯基甘氨酸。以高产率（高达 98%）和立体选择性（高达 >20:1 dr，99% ee）获得了所需的多立体螺环[环己酮-羟吲哚和 -吡唑啉酮]。
• A Mild and Direct C(sp₃)–S Cross-Coupling of Oxindoles with Thiols: Synthesis of Unsymmetrical 3-Thiooxindoles
  作者：Hui Qin、Qi Li、Jian Xu、Jie Zhang、Wei Qu、Wenyuan Liu、Feng Feng、Haopeng Sun

  DOI：10.1021/acs.joc.9b02205

  日期：2019.11.1

  Herein, an operationally simple and mild strategy to construct sulfenation of oxindoles with a series of thiols in the absence of transition metals was developed. This methodology provides an efficient way to directly form a C-S bond at the C-3 position of oxindoles under mild reaction conditions with a cheap and common solvent and base in moderate to good yields.

  本文中，开发了一种在不存在过渡金属的情况下用一系列硫醇构造羟吲哚硫化的操作简单温和的策略。这种方法学提供了一种有效的方法，可以在温和的反应条件下，以廉价和常用的溶剂和碱在中等至良好的收率下，在羟吲哚的C-3位直接形成CS键。
• A convenient synthesis of 3-methyleneoxindoles: cytotoxic metabolites of indole-3-acetic acids
  作者：Sharon Rossiter

  DOI：10.1016/s0040-4039(02)00855-9

  日期：2002.5

  3-Methyleneoxindole is a cytotoxic metabolite of indole-3-acetic acid with potential for use in cancer therapy. This species and ring-substituted analogues are conveniently synthesised from the corresponding isatins via a Peterson olefination.

  3-亚甲基羟吲哚是吲哚-3-乙酸的细胞毒性代谢产物，有可能用于癌症治疗。该物质和环取代的类似物可方便地通过彼得森烯化反应从相应的靛红合成。