3-(3-甲基-1H-吲哚-1-基)丙酸 | 57662-47-2

• 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: 3-(3-甲基-1H-吲哚-1-基)丙酸
• 中文别名: 3-(3-甲基-1H-1-吲哚)丙酸
• 英文名称: 1-skatolepropionic acid
• 英文别名: 3-(3-methylindol-1-yl)propanoic acid；3-(3-methylindol-1-yl)propionic acid；3-methylindole-1-propanoic acid；3-Methyl-indol-1-propionsaeure；<3-Methyl-indolyl-(1)>-β-propionsaeure；3-(3-Methyl-indol-1-yl)-propionsaeure；3-(3-methyl-1H-indol-1-yl)propanoic acid
• CAS: 57662-47-2
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD00052088
• 分子量: 203.241
• InChiKey: YJMBLVFDTDJZFE-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

SDS

Name:	3-(3-Methyl-1H-indol-1-yl)propanoic acid 97% Material Safety Data Sheet
Synonym:
CAS:	57662-47-2

Section 1 - Chemical Product MSDS Name:3-(3-Methyl-1H-indol-1-yl)propanoic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
57662-47-2	3-(3-Methyl-1H-indol-1-yl)propanoic ac	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 57662-47-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H13NO2
Molecular Weight: 203.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 57662-47-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(3-Methyl-1H-indol-1-yl)propanoic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 57662-47-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 57662-47-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 57662-47-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(3-甲基-1H-吲哚-1-基)丙酸 在 PPA 作用下， 反应 1.0h， 以54.5%的产率得到2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indol-1-one
  参考文献：
  名称：

  Jirkovsky, Ivo; Greenblatt, Lynne; Baudy, Reinhardt, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 11.1, p. 2278 - 2287

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(3-甲基-1H-1-吲哚)丙腈 在 氢氧化钾 作用下， 反应 3.0h， 以85%的产率得到3-(3-甲基-1H-吲哚-1-基)丙酸
  参考文献：
  名称：

  Basanagoudar, L D; Mahajanshetti, C S; Dambal, S B, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 11, p. 1018 - 1022

  摘要：

  DOI：

文献信息

• Pd-Catalyzed Intramolecular Cyclization via Direct C–H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles
  作者：Ting-Ting Wang、Lang Zhao、Yan-Jing Zhang、Wei-Wei Liao

  DOI：10.1021/acs.orglett.6b02460

  日期：2016.10.7

  Pd-catalyzed intramolecular C–H addition of indoles bearing cyanohydrin components at the C(3), C(2), and N(1) positions to nitriles is described. A wide range of functionalized partially saturated carbazoles, tetrahydropyrido[1,2-a]indole, and carbazoles can be prepared in good to excellent yields under the optimal conditions. In addition, fused polycyclic indoles with seven- or eight-membered rings

  描述了钯催化分子内C–H加成腈在腈C（3），C（2）和N（1）位置上带有氰醇成分的第一个例子。可以在最佳条件下以良好或优异的收率制备各种官能化的部分饱和咔唑，四氢吡啶并[1,2- a ]吲哚和咔唑。另外，也可以平滑地形成具有七元或八元环的稠合多环吲哚。
• Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole
  作者：Robert Coyle、Patrick McArdle、Fawaz Aldabbagh

  DOI：10.1021/jo5008543

  日期：2014.6.20

  A one-pot initiator-free Barton ester decomposition with tandem radical addition onto alkyl propiolates or phenylacetylene with aromatic substitution of the resultant vinyl radical allows convenient access to new 9-substituted 6,7-dihydropyrido[1,2-a]indoles. Propyl radical cyclizations compete when forming the expanded 7,8-dihydro-6H-azepino[1,2-a]indole system. 2-Thiopyridinyl S-radical is incorporated

  一锅式无引发剂的Barton酯分解反应，将自由基串联添加到丙炔酸烷基酯或苯乙炔上，并用芳香族取代所得的乙烯基，可以方便地获得新的9-取代的6,7-二氢吡啶并[1,2- a ]吲哚。丙基自由基环化在形成扩展的7,8-二氢-6 H-氮杂环庚烷[1,2- a ]吲哚体系时竞争。当使用未取代的吲哚-1-链烷酸前体时，将2-硫代吡啶基S-自由基结合到芳族加合物中。取代产物的X射线晶体学分析可以确定将自由基加成到反应性较低的内部炔烃上的选择性。
• Antagonists of melanin concentrating hormone effects on the melanin concetrating hormone receptor
  申请人：——

  公开号：US20030229119A1

  公开（公告）日：2003-12-11

  The present invention relates to the antagonism of the effects of melanin-concentrating hormone (MCH) through the melanin concentrating hormone receptor which is useful for the prevention or treatment of eating disorders, weight gain, obesity, abnormalities in reproduction and sexual behavior, thyroid hormone secretion, diuresis and water/electrolyte homeostasis, sensory processing, memory, sleeping, arousal, anxiety, depression, seizures, neurodegeneration and psychiatric disorders.

  本发明涉及通过黑素浓缩激素受体对黑素浓缩激素（MCH）效果的拮抗，对于预防或治疗进食障碍、体重增加、肥胖、生殖和性行为异常、甲状腺激素分泌、利尿和水/电解质平衡、感觉处理、记忆、睡眠、觉醒、焦虑、抑郁、癫痫发作、神经退行性疾病和精神疾病是有用的。
• Intramolecular Carbenoid Reactions of Pyrrole Derivatives Efficient Syntheses of Pyrrolizinone and Dihydroindolizinone
  作者：Charles W. Jefford、William Johncock

  DOI：10.1002/hlca.19830660835

  日期：1983.12.14

  The copper-catalyzed pyrolysis of 1-diazo-3-(pyrrol-1-yl)-2-propanone (1a) and 1-diazo-4-(pyrrol-1-yl)-2-butanone (1b) in benzene solution gave 1 H-pyrrolizin-2-(3H)-one (4a) and 5,6-dihydroindolizin-7 (8H)-one (4b), respectively, in quantitative yield. Similar pyrolysis of 1-diazo-4-(3-methylindol-1-yl)-2-butanone (9) was less efficient giving 1-methylbenzo[b]-5,6-dihydroindroindolizin-7 (8H)-one

  苯溶液中1-重氮-3-（吡咯-1-基）-2-丙酮（1a）和1-重氮-4-（吡咯-1-基）-2-丁酮（1b）的铜催化热解分别以定量收率得到1 H-吡咯嗪-2-（3 H）-一（4a）和5，6-二氢吲哚嗪-7（8 H）-一（4b）。1-重氮-4-（3-甲基吲哚-1-基）-2-丁酮（9）的类似热解效率较低，得到1-甲基苯并[ b ] -5,6-二氢吲哚并嗪7（8 H）-一（ 10）和4-（3-甲基吲哚-1-基）-丁-1-烯-3-酮（11），产率分别为7％和24％。
• Synthesis and biological evaluation of thieno[3,2-c]pyrazol-3-amine derivatives as potent glycogen synthase kinase 3β inhibitors for Alzheimer’s disease
  作者：Ning Yan、Fei Xie、Long-Qian Tang、De-Feng Wang、Xiang Li、Chao Liu、Zhao-Peng Liu

  DOI：10.1016/j.bioorg.2023.106663

  日期：2023.9

  as a potent GSK-3β inhibitor with an IC50 of 3.4 nM and an acceptable kinase selectivity profile. In the rat primary cortical neurons, compound 54 showed neuroprotective effects on Aβ-induced neurotoxicity. Western blot analysis indicated that 54 inhibited GSK-3β by up-regulating the expression of phosphorylated GSK-3β at Ser9 and down-regulating the expression of phosphorylated GSK-3β at Tyr216. Meanwhile

  糖原合成酶激酶 3β (GSK-3β) 是抗阿尔茨海默病 (AD) 药物开发的潜在靶标。在这项研究中，合成了一系列新型噻吩并[3,2- c ]吡唑-3-胺衍生物，并通过基于结构的药物设计评估其作为潜在的GSK-3β抑制剂的效果。具有 4-甲基吡唑部分的噻吩并[3,2- c ]吡唑-3-胺衍生物54通过 π-阳离子相互作用与 Arg141 相互作用，被鉴定为有效的 GSK-3β 抑制剂，IC 50为 3.4 nM，可接受的激酶选择性谱。在大鼠原代皮质神经元中，化合物54对 Aβ 诱导的神经毒性表现出神经保护作用。 Western blot分析表明54通过上调Ser9位点磷酸化GSK-3β的表达并下调Tyr216位点磷酸化GSK-3β的表达来抑制GSK-3β。同时， 54以剂量依赖性方式降低 Ser396 tau 磷酸化。在星形胶质细胞和小胶质细胞中， 54抑制诱导型一氧化氮合酶（iNOS）的