7-甲基-3-吲哚甲酸 | 30448-16-9

• 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: 7-甲基-3-吲哚甲酸
• 中文别名: 7-甲基-1H-吲哚-3-羧酸；7-甲基吲哚-3-甲酸
• 英文名称: 7-methyl-1H-indole-3-carboxylic acid
• CAS: 30448-16-9
• 化学式: C₁₀H₉NO₂
• mdl: MFCD06203634
• 分子量: 175.187
• InChiKey: SRYCADDCUWPWAE-UHFFFAOYSA-N

物化性质

• 熔点：
  228 °C(Solv: acetone (67-64-1))
• 沸点：
  413.3±25.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 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：
  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: 7-Methyl-1h-indole-3-carboxylic acid
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-Methyl-1h-indole-3-carboxylic acid
CAS number: 30448-16-9

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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, 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：

  7-甲基-3-吲哚甲酸 在 氢氧化钾 、 草酰氯 、 氨 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 丙酮 为溶剂， 反应 29.0h， 生成 1,7-dimethyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Novel 5-HT3 antagonists. Indole oxadiazoles

  摘要：

  The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while two hydrogen-bonding interactions are possible, only one is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 angstrom and the steric limitations are defined by van der Waals difference mapping.

  DOI：

  10.1021/jm00105a021
• 作为产物：
  描述：

  7-甲基吲哚 在 盐酸 、 sodium hydroxide 、 乙醚 、 zinc(II) chloride 作用下， 生成 7-甲基-3-吲哚甲酸
  参考文献：
  名称：

  Whalley, Journal of the Chemical Society, 1954, p. 1651

  摘要：

  DOI：

文献信息

• Copper-Mediated Cascade C–H/N–H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids
  作者：Ting-Yu Zhang、Chang Liu、Chao Chen、Jian-Xin Liu、Heng-Ye Xiang、Wei Jiang、Tong-Mei Ding、Shu-Yu Zhang

  DOI：10.1021/acs.orglett.7b03580

  日期：2018.1.5

  An efficient and environmentally benign Cu-mediated method was developed for direct cascade C–H/N–H annulation to construct polyheterocyclic indoloquinoline scaffolds. This method highlights an emerging strategy for transforming inert C–H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline

  开发了一种高效且环境友好的铜介导的方法，用于直接级联C–H / N–H环化，以构建多杂环吲哚并喹啉支架。该方法突出了在有机合成中将惰性C–H键转变为通用官能团的新兴策略，并为有效合成吲哚[3,2- c ]和[2,3- c ]喹啉生物碱提供了新的通用方法。
• QUINUCLIDINES FOR MODULATING ALPHA 7 ACTIVITY
  申请人：CoMentis, Inc.

  公开号：US20160009706A1

  公开（公告）日：2016-01-14

  Provided are substituted quinuclidine compounds, pharmaceutical compositions comprising such compounds, and methods of modulating α7 nicotinic acetylcholine receptors and treating neurological disorders using such compounds.

  提供了替代性的喹诺啡啶化合物，包括这些化合物的药物组合物，以及使用这些化合物调节α7烟碱乙酰胆碱受体和治疗神经系统疾病的方法。
• Amidoalkylindoles as Potent and Selective Cannabinoid Type 2 Receptor Agonists with in Vivo Efficacy in a Mouse Model of Multiple Sclerosis
  作者：Ying Shi、Yan-Hui Duan、Yue-Yang Ji、Zhi-Long Wang、Yan-Ran Wu、Hendra Gunosewoyo、Xiao-Yu Xie、Jian-Zhong Chen、Fan Yang、Jing Li、Jie Tang、Xin Xie、Li-Fang Yu

  DOI：10.1021/acs.jmedchem.7b00724

  日期：2017.8.24

  in potent CB2 antagonists (27 or 28, IC50 = 16–28 nM). Replacement of the amidoalkyls from 3-position to the 2-position of the indole ring dramatically increased the agonist selectivity on the CB2 over CB1 receptor. Particularly, compound 57 displayed a potent agonist activity on the CB2 receptor (EC50 = 114–142 nM) without observable agonist or antagonist activity on the CB1 receptor. Furthermore,

  选择性CB 2激动剂代表了一种有吸引力的治疗策略，可用于治疗各种疾病，而无需CB 1受体介导的精神病副作用。我们对黑市设计师药物SDB-001进行了合理的优化，从而确定了有效的和选择性的CB 2激动剂。3-氨基烷基吲哚处的7-甲氧基或7-甲硫基取代产生有效的CB 2拮抗剂（27或28，IC 50 = 16-28 nM）。从吲哚环的3位到2位取代酰胺基烷基大大提高了CB 2上的激动剂选择性，而不是CB 1上受体。特别是，化合物57对CB 2受体表现出有效的激动剂活性（EC 50 = 114–142 nM），而对CB 1受体没有明显的激动剂或拮抗剂活性。此外，在多发性硬化症的实验性自身免疫性脑脊髓炎（EAE）小鼠模型中，有57个显着减轻了临床症状并保护了小鼠中枢神经系统免受免疫损伤。
• NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：SEONG Churlmin

  公开号：US20090258876A1

  公开（公告）日：2009-10-15

  Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT 2c receptors, act selectively on the 5-HT 2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT 2c receptors.

  本公开涉及一种新的吲哚羧酸双吡啶羧酰胺衍生物，其制备方法，以及包含该衍生物作为活性成分的用于预防或治疗肥胖、泌尿系统疾病和中枢神经系统疾病的组合物。根据本发明的吲哚羧酸双吡啶羧酰胺衍生物具有高亲和力5-HT2c受体，对5-HT2c受体选择性作用，这些衍生物很少出现由其他受体引起的不良反应。由于这些衍生物有效抑制5-羟色胺活性，它们可能对治疗或预防肥胖；泌尿系统疾病，如尿失禁、早泄、勃起功能障碍和前列腺增生；以及与5-HT2c受体相关的中枢神经系统疾病，如抑郁症、焦虑症、关注症、恐慌症、癫痫、强迫症、偏头痛、睡眠障碍、戒毒、阿尔茨海默病和精神分裂症可能有用。
• Photoredox-Catalyzed Intermolecular Hydroalkylative Dearomatization of Electron-Deficient Indole Derivatives
  作者：Xu-Lun Huang、Yuan-Zheng Cheng、Xiao Zhang、Shu-Li You

  DOI：10.1021/acs.orglett.0c03759

  日期：2020.12.18

  Dearomatization of indole derivatives offers a straightforward approach to access diverse indolines. To date, the corresponding dearomative transformations involving electron-deficient indoles are limited. Herein, we report a one-electron strategy for dearomatization of electron-deficient indoles via a photoredox-catalyzed hydroalkylation employing commercially available glycine derivatives as the hydrofunctionalization

  吲哚衍生物的脱芳香化作用提供了一种直接的方法来获得各种二氢吲哚。迄今为止，涉及缺乏电子的吲哚的相应脱芳香转换是有限的。在本文中，我们报告了一种单电子策略，用于通过使用可商购的甘氨酸衍生物作为加氢官能化试剂的光氧化还原催化的加氢烷基化来对缺电子的吲哚进行脱芳香化。随后进行DBU介导的内酰胺化，以独有的选择性，以良好或优异的收率获得了结构吸引人的内酰胺融合的二氢吲哚。