N-乙酰基-3-吲哚啉酮 | 16800-68-3

• 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: N-乙酰基-3-吲哚啉酮
• 中文别名: 1-乙酰基-3-吲哚啉ONE；1-乙酰基-1,2-二氢-吲哚-3-酮；1-乙酰基-3-吲哚酮；N-乙酰基羟基吲哚；1-乙酰基-1,2,-二氢-3H-吲哚-3-酮
• 英文名称: 1-acetyl-2,3-dihydro-1H-indol-3-one
• 英文别名: 1-acetylindolin-3-one；N-acetylindoxyl；1-acetyl-3-indolinone；N-acetylindolin-3-one；1-acetyl-1,2-dihydro-3H-indol-3-one；1-acetyl-1H-indol-3(2H)-one；N-acetyl-3-indolinone；1-acetylindoxyl；1-acetyl-2H-indol-3-one
• CAS: 16800-68-3
• 化学式: C₁₀H₉NO₂
• mdl: MFCD00466593
• 分子量: 175.187
• InChiKey: AUMJJQZNOVOCGY-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  411.2±34.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Acetyl-3-indolinone
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: 1-Acetyl-3-indolinone
CAS number: 16800-68-3

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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, 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: C10H9NO2
Molecular weight: 175.2

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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

反应信息

• 作为反应物：
  描述：

  N-乙酰基-3-吲哚啉酮 在 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 22.42h， 生成 2-氯-N-(4-氯苯基)-N-(2-甲酰基-1H-吲哚-3-基)乙酰胺
  参考文献：
  名称：

  3-芳基氨基吲哚合成吲哚[3,2-b]喹啉衍生物

  摘要：

  众所周知[1]，N-乙酰基吲哚氧基(1)在乙酸中与取代的苯胺一起加热时能够形成3-芳基氨基吲哚(II)。最近 [2] 我们报道了 N-乙酰基-3-对硝基苯基氨基吲哚 (Ilc) 可用作合成 1,2 和 1,4-二氢-~5-咔啉的新衍生物的初始化合物。在这项工作中，我们研究了 3-芳基氨基吲哚 lla 的一些性质，并开发了一种合成相关吲哚 [3,2-b] 喹啉的新方法。N-乙酰基-3-芳基氨基吲哚类化合物通过已知方法[I]获得。至于单独的化合物，除了[1]中描述的化合物lie和lid之外，可能仅分离N-乙酰基-3-对-氯苯基氨基吲哚lib。我们未能分离出苯胺 (IIa) 和邻茴香胺 (lie) 的衍生物，但是用氯乙酰氯处理反应物质导致容易分离且稳定的 N-乙酰基-N'-氯乙酰基氨基吲哚 lila 和 llld（产率分别为 73 和 60*/0）。N，N'-二酰基衍生物IIIb IIId通过在

  DOI：

  10.1007/bf02219687
• 作为产物：
  描述：

  N-乙酰基吲哚-3-甲醛 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到N-乙酰基-3-吲哚啉酮
  参考文献：
  名称：

  A Convenient Synthesis of 1,2-Dihydro-3H-indol-3-ones and 1,2-Dihydro-2H-indol-2-ones by Baeyer-Villiger Oxidation

  摘要：

  取代的1H-吲哚-3-甲醛在Baeyer-Villiger重排作用下，得到了相应的取代的1,2-二氢-3H-吲哚-3-酮。研究了3-羰基和1-保护基团的影响。该反应已扩展到1H-吲哚-2-甲醛，并用于合成1-(苯磺酰基)-1H-吲哚-2-基三氟甲磺酸酯。

  DOI：

  10.1055/s-1994-25488

文献信息

• Palladium-catalyzed α-arylation of indolin-3-ones
  作者：Yu-Hsuan Chang、Wan-Ling Peng、I-Chia Chen、Hsin-Yun Hsu、Yen-Ku Wu

  DOI：10.1039/d0cc00435a

  日期：——

  A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)2 and PAd3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the

  提出了吲哚-3-酮催化α-芳基化的方法。发现包含Pd（dba）2和PAd 3的催化体系对于该转化是最佳的。该协议具有广泛的官能团兼容性，可高效合成一系列带有完全取代的碳中心的芳基化吲哚衍生物。初步的生物测定研究表明，选定的吲哚取代的吲哚3-3-酮对HCT-116癌细胞具有良好的细胞毒性。
• Design and Synthesis of Pyrano[3,2-<i>b</i>]indolones Showing Antimycobacterial Activity
  作者：Natalia Monakhova、Jana Korduláková、Anthony Vocat、Anna Egorova、Alexander Lepioshkin、Elena G. Salina、Jozef Nosek、Eva Repková、Júlia Zemanová、Helena Jurdáková、Renáta Górová、Jaroslav Roh、Giulia Degiacomi、José Camilla Sammartino、Maria Rosalia Pasca、Stewart T. Cole、Katarína Mikušová、Vadim Makarov

  DOI：10.1021/acsinfecdis.0c00622

  日期：2021.1.8

  models for replicating and nonreplicating mycobacteria, respectively. Compound 10a exhibited good activity with MIC99 values of 0.3 and 0.4 μg/mL against H37Rv and SS18b, respectively, as well as low toxicity, acceptable intracellular activity, and satisfactory metabolic stability and was selected as the lead compound for further studies. An analysis of 10a-resistant M. bovis mutants disclosed a cross-resistance

  潜在的结核分枝杆菌感染是结核病控制和新型抗分枝杆菌药物开发的最大挑战之一。通过原始的八步方案设计和合成了一系列基于吡喃并[3,2 - b ]吲哚酮的化合物。评估了合成的化合物对结核分枝杆菌菌株H37Rv和饥饿的链霉素18b（SS18b）的体外活性，分别代表了复制型和非复制型分枝杆菌的模型。化合物10a对MIC 99表现出良好的活性H37Rv和SS18b分别具有0.3和0.4μg/ mL的低毒性，低毒性，可接受的细胞内活性和令人满意的代谢稳定性，因此被选作进一步研究的先导化合物。一项对10a耐药的牛分枝杆菌突变体的分析显示，在这些菌株中与类花前寄生虫具有交叉抗性，并且改变了相对形式的辅因子F 420的相对形式。补充实验表明，F 420依赖性葡萄糖6-磷酸脱氢酶和成熟F 420的合成对于10a活性很重要。总体而言，这些研究表明10a是由未知F 420激活的前药。分枝杆菌中的依赖酶。
• Synthesis and Antitumor Properties of <i>N</i>-[2-(Dimethylamino)ethyl]carboxamide Derivatives of Fused Tetracyclic Quinolines and Quinoxalines:  A New Class of Putative Topoisomerase Inhibitors
  作者：Leslie W. Deady、Anthony J. Kaye、Graeme J. Finlay、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm970044r

  日期：1997.6.1

  does not result primarily from inhibition of topo II. The quinoxaline analogues had more varied IC50 values, being on average less cytotoxic than the quinoline derivatives, but appeared to have a similar mode of action. Overall, this new class of compounds appear to be mixed topo I/II inhibitors, up to 3-fold more cytotoxic than DACA in the human leukemia cell lines studied, with in vivo activity in

  制备了一系列四环喹啉和喹喔啉羧酰胺，并在一系列鼠类人肿瘤细胞系中评估了它们的细胞毒性。多数喹啉衍生物是通过适应Pfitzinger合成，随后进行热脱羧并使用氯甲酸异丁酯通过混合酸酐法与N，N-二甲基乙二胺偶联而制备的。喹啉类似物显示出与已知的三环a啶-4-羧酰胺混合的topoI / II抑制剂DACA相似的细胞毒性，其中噻吩和茚满类似物最具活性。他们显示出对Jurkat人白血病topo II耐药株JLA和JLC的效力几乎没有降低，表明它们的细胞毒性并非主要是由于对topo II的抑制所致。喹喔啉类似物的IC50值变化更大，与喹啉衍生物相比，其平均细胞毒性要低，但似乎具有相似的作用方式。总的来说，这类新化合物似乎是混合的topo I / II抑制剂，在研究的人类白血病细胞系中的细胞毒性比DACA高三倍，在结肠38的体内活性与DACA和阿霉素相当。
• Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites
  作者：Marta P. Carrasco、Marta Machado、Lídia Gonçalves、Moni Sharma、Jiri Gut、Amanda K. Lukens、Dyann F. Wirth、Vânia André、Maria Teresa Duarte、Rita C. Guedes、Daniel J. V. A. dos Santos、Philip J. Rosenthal、Ralph Mazitschek、Miguel Prudêncio、Rui Moreira

  DOI：10.1002/cmdc.201600327

  日期：2016.10.6

  potential of azaaurones as dual‐stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine‐resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual‐stage activity

  通过评估一个小图书馆的氮杂金龙素对抑制疟原虫的肝脏和红细胞生命周期阶段的作用，研究了氮杂金龙素作为双阶段抗疟药的潜力。针对抗氯喹疟原虫恶性疟原虫的血液阶段和伯氏疟原虫的肝阶段筛选了整个系列，产生了具有双阶段活性和亚微摩尔效价的抗红细胞寄生虫的化合物。使用基于恶性疟原虫Dd2- Sc的表型分析法对转基因寄生虫进行研究表达酵母二氢乳清酸脱氢酶（DHODH）的DHODH品系显示，其中的一种氮金龙酮衍生物具有抑制寄生虫线粒体电子传输链的潜能。在全球范围内寻找新的治疗疟疾的紧迫性，尤其是针对尚未开发的肝阶段，以及与氮杂金刚酮的化学易处理性相关的疟疾，都需要进一步发展这种化学型。总体而言，这些结果强调了氮杂紫罗兰的化学型是双阶段抗疟药的有希望的支架。
• Organocatalytic Multicomponent Reactions of 1,3-Dicarbonyls for the Synthesis of Enantioenriched Heterocycles
  作者：Xavier Bugaut、Thierry Constantieux、Haiying Du、Yohan Dudognon、Maria Sanchez Duque、Sébastien Goudedranche、Damien Bonne、Jean Rodriguez

  DOI：10.1055/s-0035-1561490

  日期：——

  Perhydropyridines 5 Conclusion and Perspective In this feature article, a general perspective of the research program aimed towards the preparation of polycyclic heterocycles by the means of enantioselective organocatalytic multicomponent reactions is presented. Guidelines for reaction design, including the selection of substrates and organocatalysts are discussed. For all transformations, scope and limitations are

  ‡两位作者均为本研究做出了同等贡献。 抽象的 在这篇专题文章中，介绍了旨在通过对映选择性有机催化多组分反应制备多环杂环的研究计划的总体观点。讨论了反应设计指南，包括底物和有机催化剂的选择。对于所有转化，都提出了范围和局限性，以及后功能化以提供多样化的杂环支架。 1引言 2种I类产品：1,4,5,6-四氢吡啶 3种II类产品：1,2,3,4-四氢吡啶 4种III类产品：桥联过氢吡啶 5结论与展望 在这篇专题文章中，介绍了旨在通过对映选择性有机催化多组分反应制备多环杂环的研究计划的总体观点。讨论了反应设计指南，包括底物和有机催化剂的选择。对于所有转化，都提出了范围和局限性，以及后功能化以提供多样化的杂环支架。 1引言 2种I类产品：1,4,5,6-四氢吡啶 3种II类产品：1,2,3,4-四氢吡啶 4种III类产品：桥联过氢吡啶 5结论与展望