7-甲氧基吲哚酮 | 7699-20-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 7-甲氧基吲哚酮
• 中文别名: 7-甲氧基-1,3-二氢-2H-吲哚-2-酮；7-甲氧基吲哚-2-酮
• 英文名称: 7-methoxyindolin-2-one
• 英文别名: 7-Methoxy-oxindol；7-methoxy-1,3-dihydroindol-2-one
• CAS: 7699-20-9
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: APQCUXBFROFCOM-UHFFFAOYSA-N

物化性质

• 熔点：
  146 °C(Solv: ethanol (64-17-5))
• 沸点：
  356.0±42.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7-Methoxyoxindole
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: 7-Methoxyoxindole
CAS number: 7699-20-9

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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: C9H9NO2
Molecular weight: 163.2

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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：

  7-甲氧基吲哚酮 生成 1-acetyl-5-methoxyindolin-2-one
  参考文献：
  名称：

  3,3-dialkyl-and 3,3-alkylene-indoline derivatives, processes for their

  摘要：

  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。

  公开号：

  US04622336A1
• 作为产物：
  描述：

  邻甲氧基苯胺 在 silver(I) acetate 、 palladium diacetate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 7-甲氧基吲哚酮
  参考文献：
  名称：

  钯催化的CH活化和2-碘乙酸酯和2-碘苯甲酸酯与苯甲酸酯的环化：氧化吲哚和菲蒽酮的一种有效方法

  摘要：

  摘要 描述了一种由苯胺合成羟吲哚和菲啶酮的简洁方法。在存在催化量的Pd（OAc）2的情况下，可以使用2-碘乙酸酯和2-碘苯甲酸酯官能化苯甲酸酯的邻位C-H键，随后进行分子内环化以生成产物。在详细的机理研究的支持下，提出了可能的涉及Pd II / Pd IV催化循环的反应机理。 描述了一种由苯胺合成羟吲哚和菲啶酮的简洁方法。在存在催化量的Pd（OAc）2的情况下，可以使用2-碘乙酸酯和2-碘苯甲酸酯官能化苯甲酸酯的邻位C-H键，随后进行分子内环化以生成产物。在详细的机理研究的支持下，提出了可能的涉及Pd II / Pd IV催化循环的反应机理。

  DOI：

  10.1055/s-0035-1561856

文献信息

• Synthesis of Lactams via Ir-Catalyzed C–H Amidation Involving Ir-Nitrene Intermediates
  作者：Jitian Liu、Wenjing Ye、Shuojin Wang、Junrong Zheng、Weiping Tang、Xiaoxun Li

  DOI：10.1021/acs.joc.0c00157

  日期：2020.3.20

  We have developed a divergent strategy for the synthesis of five- and six-membered lactams via either an amidation of sp3 C-H bonds or electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

  我们已经开发了一种通过sp3 CH键的酰胺化或Ir-nitrene中间体亲电取代芳烃来合成五元和六元内酰胺的策略。通过在二氯甲烷或六氟-2-丙醇中使用易于获得的铱催化剂，以高至优异的产率和高选择性合成了多种内酰胺。
• Zinc triflate-mediated cyclopropanation of oxindoles with vinyl diphenyl sulfonium triflate: a mild reaction with broad functional group compatibility
  作者：Mingwei Zhou、Ke En、Yimin Hu、Yufang Xu、Hong C. Shen、Xuhong Qian

  DOI：10.1039/c6ra24985j

  日期：——

  oxindoles with vinyl diphenyl sulfonium triflate salt is reported. The reaction proceeded under ambient conditions and consistently provided high yields with broad functional group tolerability. The utility for the late-stage functionalization (LSF) of complex molecules is demonstrated.

  据报道，三氟甲磺酸锌首次用于将未保护的羟吲哚与乙烯基二苯基三氟甲磺酸salt盐环丙烷化。反应在环境条件下进行，并始终提供高收率和宽泛的官能团耐受性。证明了可用于复杂分子的后期功能化（LSF）。
• Process for Preparing Substituted 1,3-dihydro-2H-indol-2-ones
  申请人：Siegel Konrad

  公开号：US20110275832A1

  公开（公告）日：2011-11-10

  Process for preparing 1,3-dihydro-2H-indol-2-ones, starting from thioalkyl-, or thiocycloalkyl-substituted indol-2-one compounds, involving a) dissolving or suspending the thioalkyl-, or thiocycloalkyl-substituted indol-2-one compounds in a polar solvent, b) adding a sulfur-containing salt to the solution or suspension, and c) heating the reaction mixture under reflux at a temperature which corresponds at most to the boiling temperature of the solvent. Use of the inventively prepared 1,3-dihydro-2H-indol-2-one as intermediates for the synthesis of fine chemicals and active ingredients from pharmacy and/or agriculture.

  从含有硫代烷基或硫代环烷基取代的吲哚-2-酮化合物开始，制备1,3-二氢-2H-吲哚-2-酮的过程，涉及a)将含有硫代烷基或硫代环烷基取代的吲哚-2-酮化合物溶解或悬浮在极性溶剂中，b)向溶液或悬浮液中加入含硫盐，以及c)在回流下加热反应混合物，温度最高不超过溶剂的沸点温度。利用创造性制备的1,3-二氢-2H-吲哚-2-酮作为合成精细化学品和药学和/或农业活性成分的中间体。
• Selective formation of γ-lactams via C–H amidation enabled by tailored iridium catalysts
  作者：Seung Youn Hong、Yoonsu Park、Yeongyu Hwang、Yeong Bum Kim、Mu-Hyun Baik、Sukbok Chang

  DOI：10.1126/science.aap7503

  日期：2018.3.2

  this rearrangement, steering the nitrene toward C–H insertion to form a variety of useful lactam rings. Science, this issue p. 1016 Theory guides design of a catalyst to cyclize amides via a nitrene intermediate otherwise prone to a competing rearrangement. Intramolecular insertion of metal nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate

  引导氮烯远离迁移 氮通常与一个或多个伙伴以三个键共享其电子。单键氮或氮烯具有异常的反应性，可以将自身插入通常惰性的 C-H 键中。但是，如果氮烯在羰基中心旁边形成，它往往会与另一侧的 C-C 键反应。洪等人。使用理论来指导抑制这种重排的铱催化剂的设计，引导氮烯向 C-H 插入以形成各种有用的内酰胺环。科学，这个问题 p。1016 理论指导设计催化剂以通过氮烯中间体环化酰胺，否则容易发生竞争性重排。金属氮烯分子内插入碳氢键形成γ-内酰胺环传统上受到异氰酸酯竞争形成的阻碍。我们报告了应用理论和机理研究来优化一类五甲基环戊二烯基铱 (III) 催化剂以抑制这种竞争途径。密度泛函理论计算表明，将辅助双齿配体的立体电子特性调节为更多的电子供体，以降低有利于所需反应的 C-H 插入势垒。这些催化剂可通过 sp3 和 sp2 C-H 酰胺化以优异的选择性将各种 1,4,2-二恶唑-5-酮、羰基硝基苯前体从羧酸中容易地转化为相应的
• METHOD FOR PRODUCING LACTAM COMPOUND, AND LACTAM COMPOUND PRODUCED THEREBY
  申请人：INSTITUTE FOR BASIC SCIENCE

  公开号：US20200331871A1

  公开（公告）日：2020-10-22

  The present invention relates to a method for producing a lactam compound from dioxazolone in the presence of a catalyst having a particular ligand, and to a lactam compound produced thereby, and can produce a lactam compound with excellent selectivity and an excellent yield by using the combination of a starting material having a particular functional group and a particular catalyst having a particular ligand.

  本发明涉及一种在具有特定配体的催化剂存在下从二氧杂环酮中生产内酰胺化合物的方法，以及由此生产的内酰胺化合物，通过使用具有特定功能基团的起始材料和具有特定配体的特定催化剂的组合，可以产生具有优异选择性和优异收率的内酰胺化合物。