甲基 3-羟基吲哚-2-羧酸盐 | 31827-04-0

• 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: 甲基 3-羟基吲哚-2-羧酸盐
• 中文别名: 甲基3-羟基吲哚-2-羧酸盐；3-羟基吲哚-2-羧酸乙酯；3-羟基吲哚-2-羧酸甲酯
• 英文名称: methyl 3-hydroxy-1H-indole-2-carboxylate
• 英文别名: methyl-3-hydroxy-1H-indole-2-carboxylate；methyl 2-hydroxy-1H-2-indolecarboxylate；methyl 3-oxoindoline-2-carboxylate；3-hydroxy-indole-2-carboxylic acid methyl ester；3-Hydroxy-indol-2-carbonsaeure-methylester；Indoxylsaeure-methylester
• CAS: 31827-04-0
• 化学式: C₁₀H₉NO₃
• mdl: MFCD00030205
• 分子量: 191.186
• InChiKey: GHRXPKBLHFSXTB-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C
• 沸点：
  360.5±22.0 °C(Predicted)
• 密度：
  1.383
• 溶解度：
  甲醇
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，也未有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其存放在阴凉、干燥处。确保工作间有良好的通风或排气装置。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Hydroxyindole-2-carboxylic acid methyl ester
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: 3-Hydroxyindole-2-carboxylic acid methyl ester
CAS number: 31827-04-0

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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: C10H9NO3
Molecular weight: 191.2

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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：

  甲基 3-羟基吲哚-2-羧酸盐 在 四(三苯基膦)钯 咪唑 、 三氯化铝 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 46.5h， 生成 methyl 3-phenyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthesis and reactivity of substituted 3-([(Trifluoromethyl)sulfonyl]oxy)-1H-indole-2-carboxylate in palladium-catalyzed reactions

  摘要：

  Palladium-catalysed Suzuki and Stille reactions of substituted 3-indolyltriflate afforded the corresponding 3-substituted indoles. By contrast, the Heck reaction of allyl alcohol with such triflates gave 2-allyloxy-3-oxoindole derivatives rather than the 3-substituted indole products as a result of a nucleophilic attack on an acyliminium intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00649-8
• 作为产物：
  描述：

  2-methoxycarbonylisatogen 在 乙醇 、 苯肼 作用下， 生成 甲基 3-羟基吲哚-2-羧酸盐
  参考文献：
  名称：

  Ruggli; Bolliger, Helvetica Chimica Acta, 1921, vol. 4, p. 640

  摘要：

  DOI：

文献信息

• Application of Magnesium Alkoxides to Syntheses of Benzoheterocyclic Compounds
  作者：Jiří Svoboda、Miloslav Nič、Jaroslav Paleček

  DOI：10.1135/cccc19930592

  日期：——

  The Dieckmann condensation of methyl [(2-methoxycarbonyl)phenyl]-X-acetates Ia-Ih (X = O, S, SO₂, NH, NCH₃) initiated by action of magnesium methoxide, ethoxide, isopropoxide and other basic reagents have been studied under various conditions. Whereas magnesium methoxide has comparable efficiency as sodium methoxide and potassium tert-butoxide in syntheses of benzoheterocyclic compounds IIa-IIh, magnesium ethoxide gives the ethyl ester IIb in medium yield, and magnesium isopropoxide is quite inefficient in the condensation reaction. The alkylation of the esters IIa, IId, and IIg with methyl chloroacetate in the presence of sodium hydride in dimethylformamide gives the diesters IIi - IIk which on action by potassium tert-butoxide undergo the cyclization reaction to give esters III.

  甲基[(2-甲氧羰基)苯基]-X-乙酸酯（X = O，S，SO₂，NH，NCH₃）在镁甲氧基、乙氧基、异丙氧基和其他碱性试剂的作用下进行的Dieckmann缩合反应在各种条件下进行了研究。镁甲氧基在合成苯杂环化合物方面具有与甲基钠和叔丁基钾相当的效率，而镁乙氧基以中等产率给出乙酸乙酯，镁异丙氧基在缩合反应中效率较低。在二甲基甲酰胺中，酯与氯乙酸甲酯在氢化钠存在下发生烷基化反应，得到二酯，经叔丁基钾作用发生环化反应，生成酯。
• [EN] PYRIDINE COMPOUNDS AS INHIBITORS OF DIPEPTIDYL PEPTIDASE IV<br/>[FR] COMPOSES PYRIDINES UTILISES COMME INHIBITEURS DE DIPEPTIDYLE PEPTIDASE IV
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2005042488A1

  公开（公告）日：2005-05-12

  A compound represented by the formula wherein R1 and R2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R3 is an optionally substituted aromatic group; R4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式表示为其中R1和R2相同或不同，每个都是可选择取代的碳氢基团或可选择取代的羟基团；R3是可选择取代的芳香基团；R4是可选择取代的氨基团；L是二价链状碳氢基团；Q是键或二价链状碳氢基团；X是氢原子、氰基、硝基、酰基、取代的羟基团、可选择取代的硫醇基团、可选择取代的氨基团或可选择取代的环状基团；但当X是乙氧羰基团时，Q为二价链状碳氢基团。该化合物具有肽酶抑制作用，可用作糖尿病等疾病的预防或治疗药物，并在功效、作用持续时间、特异性、毒性较低等方面具有优越性。
• 3-substituted indole antiproliferative angiogenesis inhibitors
  申请人：——

  公开号：US20020091148A1

  公开（公告）日：2002-07-11

  3-Substituted indole carbohydrazides having the formula 1 are useful for inhibiting angiogenesis and cell proliferation. Also disclosed are compositions which inhibit angiogenesis and cell proliferation and methods of inhibiting angiogenesis and cancer in a mammal.

  具有下式的3-取代吲哚羰肼对抑制血管生成和细胞增殖具有用处。还揭示了抑制血管生成和细胞增殖的组合物以及抑制哺乳动物中的血管生成和癌症的方法。
• Oxidative Coupling of 3‐Oxindoles with Indoles and Arenes
  作者：Houng Kang、Adriana L. Jemison、Erin Nigro、Marisa C. Kozlowski

  DOI：10.1002/cssc.201900438

  日期：2019.7.5

  A highly efficient method for the oxidative coupling of 2‐substituted 3‐oxindoles with aromatic compounds to form 2,2‐disubstituted indolin‐3‐ones with broad scope is described. This work utilized oxygen as the terminal oxidant and a base‐metal catalyst under mild conditions instead of toxic/precious‐metal reagents and higher‐molecular‐weight oxidants. Quaternary structures were produced in modest‐to‐excellent

  描述了一种高效的方法，用于2-取代的3-氧吲哚与芳族化合物的氧化偶联，形成具有广泛应用范围的2,2-二取代的吲哚-3-酮。这项工作在温和的条件下利用氧气作为末端氧化剂和贱金属催化剂，而不是使用有毒/贵金属试剂和更高分子量的氧化剂。无需预功能化，即可以中等至出色的产率（高达96％）生产四级结构。
• Improved Scalable Synthesis and Biological Activity of “Indoxyl-gal,” a Chromogenic Histochemical Used for the Identification of Lac+ Organisms
  作者：Brent Banasik、Tam Mai、Mansour Samadpour

  DOI：10.2174/1570178615666180212152030

  日期：2018.8.8

  An improved and operationally simple synthesis of 3-indoxyl-β-D-galactopyranoside (indoxyl- gal) is disclosed. Indoxyl-gal is a sensitive chromogenic histochemical used for the identification of β-galactosidase enzymatic activity (lacZ gene). Synthesis of indoxyl-gal is improved to 25% overall yield in 5 linear steps from affordable starting materials with minimal chromatography. Biological testing confirmed the detection of β-galactosidase activity in all (100%, 19 strains) coliform bacteria using membrane filtration and modified MI agar.

  披露了一种改进且操作简便的3-吲哚醇-β-D-半乳糖苷（吲哚醇-半乳糖）的合成方法。吲哚醇-半乳糖是一种敏感的着色组织化学试剂，用于识别β-半乳糖苷酶的酶活性（lacZ基因）。该合成方法的改进使得从可负担的起始材料中通过5个线性步骤获得25%的总产率，并且需要最少的色谱分离。生物测试确认使用膜过滤和改良的MI琼脂，对所有（100%，19株）大肠杆菌检测到了β-半乳糖苷酶活性。