4-甲氧基-2,3-二氢-1H-吲哚 | 7555-94-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 4-甲氧基-2,3-二氢-1H-吲哚
• 中文别名: 4-甲氧基吲哚啉
• 英文名称: 4-methoxyindoline
• 英文别名: 4-methoxy-2,3-dihydro-1H-indole；4-Methoxy-indolin
• CAS: 7555-94-4
• 化学式: C₉H₁₁NO
• mdl: MFCD07371625
• 分子量: 149.192
• InChiKey: MIOTXFNRNVNXDP-UHFFFAOYSA-N

物化性质

• 沸点：
  278.1±29.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxy-2,3-dihydro-1h-indole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Methoxy-2,3-dihydro-1h-indole
CAS number: 7555-94-4

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels.

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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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H11NO
Molecular weight: 149.2

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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：

  4-甲氧基-2,3-二氢-1H-吲哚 在 C₅₅H₄₉N₄OP₂Ru 作用下， 以 邻二甲苯 为溶剂， 140.0 ℃ 、100.0 kPa 条件下， 反应 48.0h， 以82%的产率得到4-甲氧基吲哚
  参考文献：
  名称：

  带有吡唑基-吲哚基-吡啶配体的Ru（II）-NNC配合物对N-杂环和仲醇的无受体脱氢

  摘要：

  合成了带有吡唑基-（2-吲哚-1-基）-吡啶配体的氢化钌（II）配合物，并通过NMR分析和X射线单晶晶体学测定对其结构进行了表征。这些配合物分别有效地催化了N-杂环和仲醇的无受体脱氢，表现出高催化活性，具有广泛的底物范围。本工作已经建立了构造高活性过渡金属配合物催化剂的策略，并为合成芳族N-杂环化合物和酮提供了原子经济和环境友好的方案。

  DOI：

  10.1021/acs.organomet.7b00902
• 作为产物：
  描述：

  4-甲氧基吲哚 在 硼烷-三甲胺络合物 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以94%的产率得到4-甲氧基-2,3-二氢-1H-吲哚
  参考文献：
  名称：

  N-杂环与三甲胺硼烷和 TFA 在水溶液中的无金属氢化

  摘要：

  报道了在室温下在水中用 Me 3 N · BH 3和 TFA对喹喔啉和吲哚进行无金属氢化反应。该方案的特点是使用环保水作为溶剂，无需金属催化剂，底物范围广。敏感官能团如OH-、NH 2 -、Cl-、Br-，尤其是-CN 和-CO 2 Me 具有良好的耐受性。初步机理研究表明，TFA 和 Me 3 N·BH 3分别为产品提供了质子和氢化物来源。

  DOI：

  10.1002/adsc.202200795

文献信息

• Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones
  作者：Guilin Xie、Yuhan Zhao、Changqun Cai、Guo-Jun Deng、Hang Gong

  DOI：10.1021/acs.orglett.0c03922

  日期：2021.1.15

  indole framework and/or realize indole modification. Nevertheless, the direct selective functionalization on the benzenoid core must overcome the high activity of the C-3 position and still remains highly challenging. Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually is considered as a practical

  吲哚支架是普遍存在的有用的亚结构，并且已经进行了广泛的研究以构建吲哚骨架和/或实现吲哚修饰。然而，在类苯环核上的直接选择性官能化必须克服C-3位置的高活性，并且仍然具有很高的挑战性。本文中，开发了在容易除去的导向基团存在下钯催化的吲哚的直接和特异性C-7酰化。该方法通常被认为是制备酰化吲哚的实用方法，因为在氧化条件下吲哚可以容易地转化为吲哚。尤其是，我们的策略极大地提高了二氢吲哚的烷基化收率，在先前的研究中，仅能获得令人满意的收率。此外，
• Indoles
  申请人：Eisai Co., Ltd.

  公开号：US20020019531A1

  公开（公告）日：2002-02-14

  A 1,4-substituted cyclic amine derivative represented by the following formula or a pharmacologically acceptable salt thereof: 1 wherein A, B, C, D, T, Y, and Z each represent a methine or a nitrogen linkage; R 1 , R 2 , R 3 , R 4 , and R 5 each represent a substituent; n represents 0 or an integer of 1 to 3; m represents 0 or an integer of 1 to 6; and p represents an integer of 1 to 3. The compounds have serotonin antagonism. They are therefore clinically useful as medicaments, in particular, for treating, ameliorating, and preventing spastic paralysis. They are also useful as central muscle relaxants for ameliorating myotonia.

  一种由以下公式表示的1,4-取代的环胺衍生物或其药理学上可接受的盐： 其中A、B、C、D、T、Y和Z分别表示亚甲基或氮键合物；R1、R2、R3、R4和R5分别表示取代基；n表示0或1至3的整数；m表示0或1至6的整数；p表示1至3的整数。这些化合物具有5-羟色胺拮抗作用。因此，在临床上作为药物特别有用，用于治疗、改善和预防痉挛性瘫痪。它们还可用作中枢肌肉松弛剂，改善肌张力过高。
• Potassium <i>tert</i> ‐Butoxide‐Promoted Acceptorless Dehydrogenation of N‐Heterocycles
  作者：Tingting Liu、Kaikai Wu、Liandi Wang、Zhengkun Yu

  DOI：10.1002/adsc.201900499

  日期：2019.9.3

  Potassium tert‐butoxide‐promoted acceptorless dehydrogenation of N‐heterocycles was efficiently realized for the generation of N‐heteroarenes and hydrogen gas under transition‐metal‐free conditions. In the presence of KOtBu base, a variety of six‐ and five‐membered N‐heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N‐heteroarenes and H2 gas in o‐xylene

  钾叔N-杂环的丁醇促进的acceptorless脱氢高效地实现用于N-杂芳烃和氢气的过渡金属-自由条件下产生。在存在KO t Bu碱的情况下，各种六元和五元N-杂环化合物可以有效地进行无受体脱氢，从而在140°C的邻二甲苯中提供相应的N-杂芳烃和H 2气体。本协议提供了一条通往芳香族含氮化合物和H 2气体的便捷途径。
• 内酰胺类衍生物、其制备方法及其在医药上的用途
  申请人：察略盛医药科技（上海）有限公司

  公开号：CN112079839A

  公开（公告）日：2020-12-15

  本发明涉及内酰胺类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的内酰胺类衍生物、其制备方法及其可药用的盐，以及它们作为治疗剂，特别是用于治疗炎症性疾病、神经退行性疾病、肿瘤等和相关病症和疾病的用途，其中通式(I)中的各取代基的定义与说明书中的定义相同。
• Synthesis and photolytic evaluation of a nitroindoline-caged glycine with a side chain of high negative charge for use in neuroscience
  作者：George Papageorgiou、Marco Beato、David Ogden

  DOI：10.1016/j.tet.2011.05.045

  日期：2011.7

  the GABA analogue required some modifications because of the greater hydrolytic sensitivity of the glycine compound. The phosphorylation method used here could be beneficial to the synthesis of other nitroindoline-caged amino acids, especially the related caged GABA derivative. Glycine released by laser photolysis on spinal cord neurons generated fast-rising responses and the pharmacological properties

  已经合成了神经抑制性氨基酸甘氨酸的光不稳定前体，其具有在4-烷氧基取代基处连接至二氢吲哚核的两个磷酸基团。与其他1-酰基-7-硝基二氢吲哚的光化学特性相同，当用近紫外光照射时，亚硫酸盐会在亚μs的时间尺度上释放甘氨酸。先前开发的用于制备GABA类似物的合成路线需要一些修改，因为甘氨酸化合物具有更高的水解敏感性。此处使用的磷酸化方法可能有益于合成其他硝基吲哚笼中的氨基酸，尤其是相关的笼中GABA衍生物。