2-甲氧基异烟酸甲酯 | 26156-51-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-甲氧基异烟酸甲酯
• 中文别名: 2-甲氧基-4-吡啶甲酸甲酯
• 英文名称: methyl 2-methoxyisonicotinate
• 英文别名: methyl 2-methoxy-4-pyridinecarboxylate；2-Methoxy-4-methoxycarbonyl-pyridin；methyl 2-methoxypyridine-4-carboxylate
• CAS: 26156-51-4
• 化学式: C₈H₉NO₃
• mdl: MFCD08436071
• 分子量: 167.164
• InChiKey: KVFSHVOCUQNUNV-UHFFFAOYSA-N

物化性质

• 熔点：
  36-38°
• 沸点：
  120℃ (1 Torr)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  请保持冷态

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-methoxyisonicotinate
Synonyms: Methyl 2-methoxy-4-pyridinecarboxylate

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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: Methyl 2-methoxyisonicotinate
CAS number: 26156-51-4

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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.
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: C8H9NO3
Molecular weight: 167.2

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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：

  2-甲氧基异烟酸甲酯 在 lithium aluminium tetrahydride 、 三氧化硫吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 水 、 二甲基亚砜 为溶剂， 反应 0.83h， 生成 2-甲氧基吡啶-4-醛
  参考文献：
  名称：

  EP2816032

  摘要：

  公开号：
• 作为产物：
  描述：

  2,6-二氯异烟酸甲酯 在 甲醇 、 palladium on activated charcoal 、 potassium acetate 作用下， 生成 2-甲氧基异烟酸甲酯
  参考文献：
  名称：

  实验性结核菌糖化学III。衍生物2-甲基-异烟酸酯

  摘要：

  合成了约52个2-甲基异烟酸酰肼衍生物，并测试了它们的抗结核作用。通过2-甲基异烟酰胺酰肼与醛，酮和羧酸氯化物的反应，通过2-甲基异烟酰胺酰氯与二烷基化肼的缩合，以及2-甲基异烟碱酰肼的氢化来制备衍生物。

  DOI：

  10.1002/hlca.19550380425

文献信息

• Methods and compounds for inhibiting mrp1
  申请人：——

  公开号：US20030100576A1

  公开（公告）日：2003-05-29

  The present invention further relates to a method of inhibiting MRP1 in a mammal which comprises administering to a mammal in need thereof an effective amount of a compound of formula (I).

  本发明还涉及一种抑制哺乳动物中MRP1的方法，包括向需要的哺乳动物施用化合物(I)的有效量。
• [EN] SULFONYLPIPERAZINE DERIVATIVES THAT INTERACT WITH GLUCOKINASE REGULATORY PROTEIN FOR THE TREATMENT OF DIABETES<br/>[FR] DÉRIVÉS DE SULFONYLPIPÉRAZINE QUI INTERAGISSENT AVEC LA PROTÉINE RÉGULATRICE DE LA GLUCOKINASE POUR LE TRAITEMENT DU DIABÈTE
  申请人：AMGEN INC

  公开号：WO2012027261A1

  公开（公告）日：2012-03-01

  The present invention relates to compounds of Formula I, or pharmaceutically acceptable salts thereof, that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where glucokinase regulatory protein is involved using the compounds, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions that contain the compounds, or pharmaceutically acceptable salts thereof.

  本发明涉及与葡萄糖激酶调节蛋白相互作用的化合物I式，或其药用盐，此外，本发明涉及使用这些化合物或其药用盐治疗2型糖尿病和其他涉及葡萄糖激酶调节蛋白的疾病和/或症状的方法，以及含有这些化合物或其药用盐的药物组合物。
• Iridium-catalyzed C–H borylation of pyridines
  作者：Scott A. Sadler、Hazmi Tajuddin、Ibraheem A. I. Mkhalid、Andrei S. Batsanov、David Albesa-Jove、Man Sing Cheung、Aoife C. Maxwell、Lena Shukla、Bryan Roberts、David C. Blakemore、Zhenyang Lin、Todd B. Marder、Patrick G. Steel

  DOI：10.1039/c4ob01565g

  日期：——

  The iridium-catalysed C–H borylation is a valuable and attractive method for the preparation of aryl and heteroaryl boronates. However, application of this methodology for the preparation of pyridyl and related azinyl boronates can be challenged by low reactivity and propensity for rapid protodeborylation, particularly for a boronate ester ortho to the azinyl nitrogen. Competition experiments have revealed that the low reactivity is due to inhibition of the active catalyst through coordination of the azinyl nitrogen lone pair at the vacant site on the iridium. This effect can be overcome through the incorporation of a substituent at C-2. Moreover, when this is sufficiently electron-withdrawing protodeborylation is sufficiently slowed to permit isolation and purification of the C-6 boronate ester. Following functionalization, reduction of the directing C-2 substituent provides the product arising from formal ortho borylation of an unhindered pyridine ring.

  铱催化的C-H硼化是一种有价值且有吸引力的方法，用于制备芳基和杂芳基硼酸酯。然而，这种方法在制备吡啶基及相关氮杂基硼酸酯时可能面临反应活性低和快速质子脱硼化的挑战，尤其是当硼酸酯位于氮杂基氮原子的邻位时。竞争实验揭示，低反应活性是由于氮杂基氮原子的孤对电子在铱的空位上配位，抑制了活性催化剂。通过在C-2位引入取代基可以克服这一效应。此外，当该取代基足够吸电子时，质子脱硼化过程会被足够减缓，从而允许分离和纯化C-6硼酸酯。经过功能化后，导向C-2取代基的还原提供了源自未受阻吡啶环形式邻位硼化的产物。
• Nickel-Catalyzed Carboxylation of Aryl and Heteroaryl Fluorosulfates Using Carbon Dioxide
  作者：Cong Ma、Chuan-Qi Zhao、Xue-Tao Xu、Zhao-Ming Li、Xiang-Yang Wang、Kun Zhang、Tian-Sheng Mei

  DOI：10.1021/acs.orglett.9b00836

  日期：2019.4.5

  The development of efficient and practical methods to construct carboxylic acids using CO2 as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO2 is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed.

  利用CO 2作为C1合成子来构建羧酸的有效且实用的方法的开发非常重要。描述了用CO 2进行镍催化的芳基氟代硫酸盐和杂芳基氟代硫酸盐的羧化，在温和条件下提供芳烃羧酸，具有良好的产率或优异的产率。另外，开发了一种单锅酚氟代硫酸化/羧化。
• Discovery and biological evaluation of novel 4-amino-2-phenylpyrimidine derivatives as potent and orally active GPR119 agonists
  作者：Kenji Negoro、Yasuhiro Yonetoku、Hana Misawa-Mukai、Wataru Hamaguchi、Tatsuya Maruyama、Shigeru Yoshida、Makoto Takeuchi、Mitsuaki Ohta

  DOI：10.1016/j.bmc.2012.06.049

  日期：2012.9

  Novel 4-amino-2-phenylpyrimidine derivatives were synthesized and evaluated as GPR119 agonists. Optimization of the substituents on the phenyl ring at the 2-position and the amino group at the 4-position led to the identification of 3,4-dihalogenated and 2,4,5-trihalogenated phenyl derivatives showing potent GPR119 agonistic activity. The advanced analog (2R)-3-[2-(4-chloro-2,5-difluorophenyl)-6-

  合成了新型的4-氨基-2-苯基嘧啶衍生物，并将其评估为GPR119激动剂。优化2-位苯环上的取代基和4-位氨基上的取代基，可以鉴定出显示出强效GPR119激动活性的3,4-二卤代和2,4,5-三卤代苯基衍生物。发现高级类似物（2 R）-3-[2-（4-氯-2,5-二氟苯基）-6-乙基嘧啶-4-基]氨基}丙烷-1,2-二醇（24g）可以改善在小鼠中口服1 mg / kg的葡萄糖耐量，并在小鼠和猴子中表现出出色的药代动力学特征。在单日治疗一周后，化合物24g在糖尿病kk / Ay小鼠中也显示出优异的抗糖尿病作用。这些结果表明，新型GPR119激动剂24g 不仅可以通过增强葡萄糖依赖性胰岛素的分泌来改善葡萄糖耐受性，还可以通过保留胰腺β细胞功能来改善葡萄糖耐受性。