4-甲氧基烟酸甲酯 | 10177-32-9

• 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: 4-甲氧基烟酸甲酯
• 英文名称: methyl 4-methoxynicotinate
• 英文别名: 4-methoxy-nicotinic acid methyl ester；4-Methoxy-nicotinsaeure-methylester；3-Carbomethoxy-4-methoxy-pyridin；4-Methoxy-5-carbomethoxypyridin；Methyl-4-methoxy-nicotinat；4-Methoxy-nicotinat；methyl 4-methoxypyridine-3-carboxylate
• CAS: 10177-32-9
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: GPYPBIOSNPTCAU-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  250.9±20.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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

• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-methoxynicotinate
Synonyms: Methyl 4-methoxypyridine-3-carboxylate

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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 4-methoxynicotinate
CAS number: 10177-32-9

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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.
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：

  4-甲氧基烟酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以96%的产率得到(4-甲氧基-3-吡啶基)甲醇
  参考文献：
  名称：

  Syntheses of Ortho-Hydroxymethylpyridinols and Dioxaphosphorino[m,n-x]pyridines

  摘要：

  Dioxaphosphorino [m,n-x]pyridines compounds have been prepared by condensation of methyl dichlorophosphate with new ortho-hydroxymethylpyridinols.

  DOI：

  10.1080/00397919608004536
• 作为产物：
  描述：

  3-甲基-4-硝基吡啶-N-氧化物 在 盐酸 、 potassium permanganate 、 三氯化磷 作用下， 以 氯仿 、 水 为溶剂， 反应 7.33h， 生成 4-甲氧基烟酸甲酯
  参考文献：
  名称：

  Syntheses of Ortho-Hydroxymethylpyridinols and Dioxaphosphorino[m,n-x]pyridines

  摘要：

  Dioxaphosphorino [m,n-x]pyridines compounds have been prepared by condensation of methyl dichlorophosphate with new ortho-hydroxymethylpyridinols.

  DOI：

  10.1080/00397919608004536

文献信息

• Compounds for and methods of treating diseases
  申请人：Alterity Therapeutics Limited

  公开号：US11155547B1

  公开（公告）日：2021-10-26

  The present invention provides heterocyclic compounds of formula (I) that modulate biological metals and to pharmaceutical compositions containing such compounds. The invention particularly relates to compounds that modulate iron and to compounds for the treatment of diseases, particularly neurological diseases such as Parkinson's disease (PD), Alzheimer's disease (AD), Alzheimer-type dementia, Huntington's disease (HD), amyotrophic lateral sclerosis (ALS), frontotemporal dementia (FTD) and multiple system atrophy (MSA).

  本发明提供了式（I）的杂环化合物，其调节生物金属，并含有这种化合物的药物组合物。本发明特别涉及调节铁元素的化合物，以及用于治疗疾病的化合物，特别是神经系统疾病，如帕金森病（PD）、阿尔茨海默病（AD）、阿尔茨海默型痴呆、亨廷顿病（HD）、肌萎缩侧索硬化（ALS）、额颞叶痴呆（FTD）和多系统萎缩（MSA）。
• An umpolung approach to the hydroboration of pyridines: a novel and efficient synthesis of <i>N</i>-H 1,4-dihydropyridines
  作者：Huan Yang、Li Zhang、Fei-Yu Zhou、Lei Jiao

  DOI：10.1039/c9sc05627k

  日期：——

  boryl anion addition to pyridine, which produces an N-boryl pyridyl anion complex, and the subsequent protonation of the anion complex. This process enables a simple and efficient method for the synthesis of multi-substituted N-H 1,4-dihydropyridine (1,4-DHP) derivatives that are difficult to prepare using established methods. Furthermore, this method allows for facile preparation of 4-deuterated 1

  吡啶与二硼(4) 化合物和质子源的第一次逆硼氢化反应是在简单的碱性和无催化剂条件下实现的。该过程包括将正式的硼基阴离子加成到吡啶中，生成N-硼基吡啶基阴离子络合物，然后使阴离子络合物质子化。该方法能够以简单有效的方法合成多取代的N -H 1,4-二氢吡啶 (1,4-DHP) 衍生物，这些衍生物难以使用已建立的方法制备。此外，该方法允许从易于获取的氘离子源轻松制备 4-氘化 1,4-DHP。这种逆硼氢化反应代表了一种吡啶官能化的新模式。
• Antiemetic, psychosomatic and antipsychotic heterocyclic pyridine
  申请人：Ciba-Geigy Corporation

  公开号：US04089960A1

  公开（公告）日：1978-05-16

  The present invention provides new basically substituted pyridinecarboxamides having the formula I ##STR1## wherein R.sub.1 represents lower alkyl and --OR.sub.1 is in the adjacent position to the carboxamide group, R.sub.2 represents lower alkyl or an ethylene radical which is attached to one of the trivalent radicals designated as A and the nitrogen atom located between it to form a 6-membered ring, A represents a divalent saturated hydrocarbon radical which encompasses at most a single ring with 5 or 6 ring members and contains not more than 7 carbon atoms and whose two linkage positions are separated by (3-m) to 4 carbon atoms, or, if R.sub.2 is an ethylene radical, represents the 1-propanyl-3-ylidene radical, if m s 1, or the 1,2,4-butane-triyl radical, if m is 0, And one of the factors m and n is 0 and the other is 1, and, if desired, the ring B is further substituted, and the acid addition salts of the compounds of the formula I. These new substances possess useful pharmacological properties, in particular antiemetic, psychosomatic and antipsychotic activity and can be used for the treatment of thought disturbances and of states of psychomotor excitation. Specific embodiments are N-[(1-ethyl-2-pyrrolidinyl)-methyl]-2,6-dimethoxynicotinamide and the pharmaceutically acceptable acid addition salts thereof.

  本发明提供了一种新的基本取代吡啶羧酰胺，其具有以下式I ##STR1## 其中R.sub.1代表较低的烷基，--OR.sub.1位于与羧酰胺基团相邻的位置，R.sub.2代表较低的烷基或与被标记为A的三价基团之一和位于其之间的氮原子形成6元环的乙烯基，A代表二价饱和碳氢基团，最多包含一个由5或6个环成员组成的环，并且含有不超过7个碳原子，其两个连接位置之间相隔(3-m)至4个碳原子，或者如果R.sub.2是一个乙烯基，则代表1-丙基-3-亚基基团，如果m≤1，或者1,2,4-丁烷三基基团，如果m为0，而m和n中的一个因子为0，另一个为1，如果需要，环B进一步取代，并且具有上述式I的化合物的酸盐加合物。这些新物质具有有用的药理特性，特别是抗恶心、精神身体反应和抗精神病活性，并可用于治疗思维障碍和精神运动兴奋状态。具体实施例包括N-[(1-乙基-2-吡咯烷基)-甲基]-2,6-二甲氧基烟酰胺及其药用可接受的酸盐加合物。
• The Reaction of N-Trimethylsilyl-Substituted Heteroarylamines with Esters and Thioesters: An Efficient Protocol To Access Diheteroarylamides
  作者：Ana Koperniku、Maryam Zamiri、David Grierson

  DOI：10.1055/s-0037-1611435

  日期：2019.4

  representative 4-pyridinone-based carboxylic acid were sufficiently activated to react efficiently in amide coupling reactions with the amide anion generated in situ from the N-trimethylsilyl derivative of different weakly nucleophilic heteroarylamines. In acetonitrile as solvent, the precipitated diheteroarylamide products were isolated in pure form by vacuum filtration. This simple amide bond forming protocol

  抽象的 具有代表性的基于4-吡啶酮的羧酸的S-苄基硫酯和甲酯衍生物被充分活化以在酰胺偶联反应中与从不同的弱亲核性杂芳基胺的N-三甲基甲硅烷基衍生物原位产生的酰胺阴离子有效地反应。在乙腈作为溶剂中，通过真空过滤以纯净的形式分离出沉淀的二杂芳基酰胺产物。这种简单的酰胺键形成方案可以很容易地适应化合物库的平行合成。 具有代表性的基于4-吡啶酮的羧酸的S-苄基硫酯和甲酯衍生物被充分活化以在酰胺偶联反应中与从不同的弱亲核性杂芳基胺的N-三甲基甲硅烷基衍生物原位产生的酰胺阴离子有效地反应。在乙腈作为溶剂中，通过真空过滤以纯净的形式分离出沉淀的二杂芳基酰胺产物。这种简单的酰胺键形成方案可以很容易地适应化合物库的平行合成。
• Enzymatic Synthesis of Pyridine Nucleotides. Structural Property of Some New NAD-analogs, and Base Conditions Available for the Analog Formation
  作者：Shuichi Tono-oka

  DOI：10.1246/bcsj.55.1531

  日期：1982.5

  prepared by a base-exchange reaction catalyzed by pig-brain NADase. The analogs produced from methyl 4-(methylamino)- and 4-(dimethylamino)nicotinates were proved to be 1,4-dihydropyridine form. On the contrary, the analog obtained from 4-(acetylamino)nicotinamide was shown to be a quaternary pyridinium form. Moreover, an unexpected analog of 1,4-dihydro-4-pyridinone form was given by 4-methoxynicotinamide

  通过猪脑 NADase 催化的碱基交换反应制备了一些新的 β-NAD 类似物。由 4-(甲氨基)-和 4-(二甲氨基)烟酸甲酯产生的类似物被证明是 1,4-二氢吡啶形式。相反，从 4-（乙酰氨基）烟酰胺获得的类似物显示为季吡啶鎓形式。此外，1,4-二氢-4-吡啶酮形式的意外类似物由4-甲氧基烟酰胺给出。已证明对于 NAD 类似物的形成是必不可少的，相关吡啶碱的环氮至少应该在 pH 7 附近没有质子化。有趣的是，发现具有 4-氨基、甲氨基和二甲氨基的烟酸是环氮原子比它们各自的甲酯更碱性。

表征谱图