2-甲基烟酸甲酯 | 65719-09-7

• 物质功能分类: 医药中间体 - 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-甲基烟酸甲酯
• 中文别名: 2-甲基吡啶-3-羧酸甲酯
• 英文名称: methyl 2-methylnicotinate
• 英文别名: methyl 2-methylpyridine-3-carboxylate；2-Methylnicotinic acid methyl ester
• CAS: 65719-09-7
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: KLHWBYHFWALOIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  102-104°C 10mm
• 密度：
  1.104±0.06 g/cm3(Predicted)
• 闪点：
  102-104°C/10mm
• 溶解度：
  易溶于氯仿和甲醇。
• 稳定性/保质期：

  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/38
• 海关编码：
  2933399090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。请确保其远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Methyl 2-methylnicotinate
Product Name:
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
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P362: Take off contaminated clothing and wash before reuse
P321: Specific treatment (see on this label)
P332+P313: If skin irritation occurs: Get medical advice/attention
P337+P313: If eye irritation persists get medical advice/attention

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Section 3. Composition/information on ingredients.
Methyl 2-methylnicotinate
Ingredient name:
CAS number: 65719-09-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H9NO2
Molecular weight: 151.2

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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

制备方法与用途

外观：无色至深黄色油状物。

用途：2-甲基烟酸甲酯是烟酸的酯衍生物，主要用于制备含有杂环的双环氮化合物。此外，它还是可卡因热解的产物。

反应信息

• 作为反应物：
  描述：

  2-甲基烟酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四丁基氟化铵 、 氢气 作用下， 以 甲醇 、 四氯化碳 、 乙腈 为溶剂， 反应 36.0h， 生成 7,8-二氢-1,6-萘啶-5(6H)-酮
  参考文献：
  名称：

  [EN] INDOLE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS
  [FR] COMPOSÉS INDOLIQUES UTILES EN TANT QUE MODULATEURS DU RÉCEPTEUR DES ANDROGÈNES

  摘要：

  本文提供了一种公式（V）的化合物，它们与雄激素受体（AR）的BF3结合，可以调节AR以治疗肯尼迪病。

  公开号：

  WO2022020342A1
• 作为产物：
  描述：

  3-羟基-2-甲基吡啶 在 锰 、 bis(triphenylphosphine)nickel(II) chloride 、 硫酰氟 、 新铜试剂 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 44.0h， 生成 2-甲基烟酸甲酯
  参考文献：
  名称：

  使用二氧化碳的镍催化芳基和杂芳基氟代硫酸盐的羧化反应

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.9b00836

文献信息

• Phosphoric Acid Mediated Light‐Induced Minisci C−H Alkylation of <i>N</i> ‐Heteroarenes
  作者：Songyang Jin、Xinxin Geng、Yujun Li、Ke Zheng

  DOI：10.1002/ejoc.202001538

  日期：2021.2.12

  A visible light‐intduced/phosphate‐mediated light‐induced Minisci‐type reaction under metal‐ and photocatalyst‐free condition was developed, which provided an efficient and environmentally friendly way to access functionalized N‐heteroarenes. The transformation underwent a radical pathway, and the diphenyl phosphate played a key role in the catalytic cycle via hydrogen bonding.

  在无金属和无光催化剂的条件下，开发了可见光诱导/磷酸盐介导的光致Minisci型反应，这为获得功能化的N-杂芳烃提供了一种有效且环保的方法。转化经历了自由基途径，而磷酸二苯酯通过氢键在催化循环中起着关键作用。
• Discovery of Functionally Selective 7,8,9,10-Tetrahydro-7,10-ethano-1,2,4-triazolo[3,4-<i>a</i>]phthalazines as GABA_A Receptor Agonists at the α₃ Subunit
  作者：Michael G. N. Russell、Robert W. Carling、John R. Atack、Frances A. Bromidge、Susan M. Cook、Peter Hunt、Catherine Isted、Matt Lucas、Ruth M. McKernan、Andrew Mitchinson、Kevin W. Moore、Robert Narquizian、Alison J. Macaulay、David Thomas、Sally-Anne Thompson、Keith A. Wafford、José L. Castro

  DOI：10.1021/jm040883v

  日期：2005.3.1

  We have previously identified the 7,8,9,10-tetrahydro-7,10-ethano-1,2,4-triazolo[3,4-a]phthalazine (1) as a potent partial agonist for the alpha(3) receptor subtype with 5-fold selectivity in binding affinity over alpha(1). This paper describes a detailed investigation of the substituents on this core structure at both the 3- and 6-positions. Despite evaluating a wide range of groups, the maximum selectivity

  我们之前已经确定了7,8,9,10-四氢-7,10-乙醇-1,2,4-三唑并[3,4-a]酞嗪（1）是α（3）的有效部分激动剂。受体亚型，对α（1）的结合亲和力具有5倍的选择性。本文描述了在此核心结构的3位和6位上的取代基的详细研究。尽管评估了广泛的组，但相对于alpha（1）亚型，对alpha（3）亚型的亲和力可达到的最大选择性是12倍（对于57）。尽管大多数类似物在功效上均未显示选择性，但一些类似物确实在α（1）处表现出部分激动作用，而在α（3）处表现出拮抗作用（例如25和75）。但是，测试了两个类似物（93和96），它们都在6位上有三唑取代基，显示出对alpha（3）亚型的疗效明显高于alpha（1）亚型。这是该系列中可以在所需方向上实现选择性的第一个迹象。
• NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUND, AS WELL AS PREPARATION METHOD, INTERMEDIATE, COMPOSITION AND APPLICATION THEREOF
  申请人：SHANGHAI PHARMACEUTICALS HOLDING CO., LTD.

  公开号：US20190010153A1

  公开（公告）日：2019-01-10

  The present invention discloses a nitrogen-containing fused heterocyclic compound, as well as a preparation method, intermediate, composition and application thereof. The nitrogen-containing fused heterocyclic compound of the present invention as represented by formula (I), as well as the pharmaceutically acceptable salt, enantiomer, diastereomer, tautomer, solvate, metabolite or drug precursor thereof, exhibit a high selectivity and a high inhibitory activity with respect to CDK4 and CDK6 at a molecular level, an excellent inhibitory activity with respect to breast cancer cells at a cellular level, and significant inhibition of tumor cell proliferation associated with cyclin-dependent kinase activity at an animal level. The invention also exhibits a good stability with respect to human or mouse liver microsomes without significant inhibition of metabolic enzymes, good in vivo absorption in mice and rats, a high bioavailability and good druggability.

  本发明公开了一种含氮融合杂环化合物，以及其制备方法、中间体、组合物和应用。本发明的含氮融合杂环化合物如公式(I)所示，以及其药学上可接受的盐、对映体、二对映体、互变异构体、溶剂合物、代谢物或药物前体，在分子水平上对CDK4和CDK6表现出高选择性和高抑制活性，在细胞水平上对乳腺癌细胞表现出优异的抑制活性，并在动物水平上显著抑制与细胞周期依赖性激酶活性相关的肿瘤细胞增殖。该发明还在人类或小鼠肝微粒体中表现出良好的稳定性，没有显著抑制代谢酶，对小鼠和大鼠体内吸收良好，具有高生物利用度和良好的药物可用性。
• Light‐Promoted Minisci Coupling Reaction of Ethers and Aza Aromatics Catalyzed by Au/TiO ₂ Heterogeneous Photocatalyst
  作者：Zhanchong Li、Liangying Wu、Jiabao Guo、Yifei Shao、Yang Song、Yuzhou Ding、Li Zhu、Xiaoquan Yao

  DOI：10.1002/cctc.202100298

  日期：2021.8.20

  light-promoted Minisci oxidative coupling reaction of ether and aza aromatics by using oxygen as green oxidant and only catalytic amount of acid as additive. The protocol shows a good functional group tolerance as well as good to excellent yields for various substrates. With mechanistic studies, Au/TiO2 nanocomposite proved to be an efficient photocatalyst to activate C−H bond via a SEO approach of heteroatoms

  在本文中，Au/TiO 2纳米复合材料被合成并用作有机反应的高效绿色光催化剂。通过溶剂热法制备了具有高活性（001）晶面的片状锐钛矿二氧化钛材料。然后通过液相还原法将金纳米粒子负载在TiO 2表面，得到具有良好光催化活性的Au/TiO 2材料。Au/TiO 2利用纳米复合材料作为光催化剂，以氧气为绿色氧化剂，仅以催化量的酸为添加剂，开发了醚和氮杂芳烃的光促进 Minisci 氧化偶联反应。该协议显示出良好的官能团耐受性以及各种底物的优良产量。通过机理研究，Au/TiO 2纳米复合材料被证明是一种通过杂原子的 SEO 方法激活 C-H 键的有效光催化剂。此外，固体半导体光催化剂表现出良好的回收性能，易于回收和再利用，且收率不会显着降低。
• [EN] NEW COMPOUNDS V<br/>[FR] NOUVEAUX COMPOSÉS V
  申请人：BIOVITRUM AB PUBL

  公开号：WO2009147211A1

  公开（公告）日：2009-12-10

  The present invention relates to new compounds of formula (I), to pharmaceutical compositions comprising these compounds and to the use of these compounds as leptin receptor modulator mimetics in the preparation of medicaments against conditions associated with weight gain, type 2 diabetes and dyslipidemias.

  本发明涉及式(I)的新化合物，包含这些化合物的药物组合物，以及这些化合物作为瘦素受体调节剂模拟物在制备用于治疗与体重增加、2型糖尿病和血脂异常相关的药物的用途。