1,5-二甲基-1H-吡唑-3-甲酸乙酯 | 5744-51-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,5-二甲基-1H-吡唑-3-甲酸乙酯
• 中文别名: 1,5-二甲基-1H-吡唑-3-羧酸乙酯；1,5-二甲基-1H-吡唑-5-羧酸乙酯；1,5-二甲基吡唑-3-甲酸乙酯；1,5-二甲基吡唑-3-羧酸乙酯
• 英文名称: ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate
• 英文别名: ethyl 1,5-dimethylpyrazole-3-carboxylate；1,5-dimethylpyrazole-3-carboxylic acid ethyl ester；1,5-dimethyl-3-ethoxycarbonylpyrazole；1,5-Dimethyl-pyrazol-3-carbonsaeure-ethylester
• CAS: 5744-51-4
• 化学式: C₈H₁₂N₂O₂
• mdl: MFCD00085071
• 分子量: 168.195
• InChiKey: OJPXVXXMBWKEAT-UHFFFAOYSA-N

物化性质

• 熔点：
  39-41°C
• 沸点：
  154°C 10mm
• 密度：
  1.12±0.1 g/cm3 (20 ºC 760 Torr)
• 闪点：
  110.3±21.8℃

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：
  0.5
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 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：
  2933199090
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 危险性防范说明：
  P261,P305+P351+P338
• 储存条件：
  存放于惰性气体中；避免接触湿气（以免分解）。

SDS

Name:	Ethyl 1 5-dimethyl-1H-pyrazole-3-carboxylate tech Material Safety Data Sheet
Synonym:
CAS:	5744-51-4

Section 1 - Chemical Product MSDS Name:Ethyl 1 5-dimethyl-1H-pyrazole-3-carboxylate tech Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5744-51-4	Ethyl 1,5-dimethyl-1H-pyrazole-3-carbo		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5744-51-4: 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: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 154 deg C @10mmHg
Freezing/Melting Point: 39 - 41 deg C
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: C8H12N2O2
Molecular Weight: 168

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, bases, amines.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5744-51-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 5744-51-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5744-51-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5744-51-4 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

制备方法与用途

1,5-二甲基-1H-吡唑-3-羧酸乙酯是一种生物化学试剂，可用于生物材料或有机化合物，在生命科学相关研究中发挥重要作用。

反应信息

• 作为反应物：
  描述：

  1,5-二甲基-1H-吡唑-3-甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 以47.7 %的产率得到4-溴-1,5-二甲基-1H-吡唑-3-羧酸乙酯
  参考文献：
  名称：

  使用吡唑衍生抑制剂探索间日疟原虫 N-肉豆蔻酰转移酶内的亚位点选择性

  摘要：

  N-肉豆蔻酰转移酶（NMT）是一个有前途的抗疟药物靶点。尽管间日疟原虫和人类 NMT 之间的生化相似，但我们最近的研究表明，高选择性是可以实现的。在此，我们报告了Pv NMT 抑制化合物，旨在确定新的选择性机制。抑制剂中的吡唑部分附加了各种官能团，以靶向肽结合裂口下方形成的口袋。抑制剂核心基团的极性、亲脂性和大小也发生变化，以探测通道附近的水结构。选择性指数值范围为 0.8 至 125.3。两种选择性化合物的共晶结构（在 1.97 和 2.43 Å 处测定）表明，延伸部分结合了目标口袋，但具有不同的稳定性。引入核心的大萘部分与蛋白质结合水结合，而不是取代蛋白质结合水，导致抑制剂位置发生变化并扩大结合位点。我们的结构-活性数据为指导未来抑制剂优化提供了概念基础。

  DOI：

  10.1021/acs.jmedchem.4c00168
• 作为产物：
  描述：

  甲基肼 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以84.8%的产率得到1,5-二甲基-1H-吡唑-3-甲酸乙酯
  参考文献：
  名称：

  一种劳拉替尼中间体1,5-二甲基-1H-吡唑-3-甲酸乙酯的合成工艺

  摘要：

  本发明涉及一种劳拉替尼中间体1,5‑二甲基‑1H‑吡唑‑3‑甲酸乙酯的合成工艺，包括如下步骤：第一步，草酸二乙酯与丙酮反应，生成中间产物；第二步，第一步制得的中间产物与甲基肼反应，生成1,5‑二甲基‑1H‑吡唑‑3‑甲酸乙酯。本发明以草酸二乙酯、丙酮为主原料，经缩合、环合两步反应，合成目标产物。尤其在第二步环合反应的时候，通过控制温度、加料顺序、控制反应液的pH值，有效增加产物的转化率，抑制杂质的含量，提高了产品的纯度和收率。

  公开号：

  CN112390758A

文献信息

• [EN] ARYL ANNULATED MACROCYCLIC INDOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDOLE MACROCYCLIQUES ANNELÉS ARYLE
  申请人：BAYER AG

  公开号：WO2019096907A1

  公开（公告）日：2019-05-23

  The present invention relates to aryl annulated macrocyclic indole derivatives of general formula (I): in which R1, R2, R3, R4, R5, R6, A and L are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active ingredients.

  本发明涉及通式（I）所示的芳基环化大环吲哚衍生物，其中R1、R2、R3、R4、R5、R6、A和L如本文所定义，制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是治疗过度增殖性疾病的药物组合物，作为唯一药剂或与其他活性成分结合使用。
• [EN] MACROCYCLIC FLUORINE SUBSTITUTED INDOLE DERIVATIVES AS MCL-1 INHIBITORS, FOR USE IN THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS D'INDOLE MACROCYCLIQUES SUBSTITUÉS PAR DU FLUOR UTILISÉS EN TANT QU'INHIBITEURS DE MCL-1, DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DU CANCER
  申请人：BROAD INST INC

  公开号：WO2019096909A1

  公开（公告）日：2019-05-23

  The present invention relates to macrocyclic indole derivatives of general formula (I) : in which R1, R2, R3, R4, R5, R6, A and L are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active ingredients.

  本发明涉及一般式(I)的大环吲哚衍生物，其中R1、R2、R3、R4、R5、R6、A和L如本文所定义，制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是用作唯一活性成分或与其他活性成分结合。
• [EN] MCL-1 INHIBITOR MACROCYCLE COMPOUNDS FOR USE IN CLINICAL MANAGEMENT OF CONDITIONS CAUSED OR MEDIATED BY SENESCENT CELLS AND FOR TREATING CANCER<br/>[FR] COMPOSÉS MACROCYCLIQUES INHIBITEURS DE MCL-1 DESTINÉS À ÊTRE UTILISÉES DANS LA GESTION CLINIQUE D'ÉTATS PATHOLOGIQUES PROVOQUÉS OU INDUITS PAR DES CELLULES SÉNESCENTES AINSI QUE DANS LE TRAITEMENT DU CANCER
  申请人：UNITY BIOTECHNOLOGY INC

  公开号：WO2021092053A1

  公开（公告）日：2021-05-14

  This disclosure provides small-molecule compounds with Mcl-l inhibitory activity. Compounds provided in this disclosure promote apoptosis in senescent cells, particularly when combined with inhibitors of other Bcl family proteins. Compounds provided in this disclosure also promote apoptosis in cancer cells. Such compounds can be developed for treating senescent-related conditions, or as chemotherapeutic agents.

  本公开提供了具有Mcl-1抑制活性的小分子化合物。本公开提供的化合物能促进衰老细胞的凋亡，尤其是当与其他Bcl家族蛋白的抑制剂结合使用时。本公开还提供的化合物能促进癌细胞的凋亡。这类化合物可以开发用于治疗与衰老相关的状况，或作为化疗药物。
• Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies
  作者：Said Tighadouini、Smaail Radi、Farid Abrigach、Redouane Benabbes、Driss Eddike、Monique Tillard

  DOI：10.1021/acs.jcim.8b00828

  日期：2019.4.22

  synthesized compounds were confirmed by elemental analysis, FT-IR, ESI/LC-MS, and 1H and 13C NMR. In addition, X-ray diffraction analysis (XRD) was used to determine the single crystal structure of compound 10. All of the new compounds have been evaluated for their in vitro antifungal and antibacterial activities. Interestingly, the results indicate that most of the compounds display notable antifungal activity

  制备了具有β-酮-烯醇功能并大大改善了药效团性质的新的有前途的抑制剂家族。本文中，已设计并合成了一系列带有吡唑部分的β-酮-烯醇基的新型衍生物，并通过一步法使用混合克莱森缩合法合成，以开发潜在的抗真菌剂。通过元素分析，FT-IR，ESI / LC-MS以及1 H和13 C NMR确认合成的化合物的结构。此外，X射线衍射分析（XRD）用于确定化合物10的单晶结构。所有新化合物均经过了体外抗真菌和抗菌活性的评估。有趣的是，结果表明大多数化合物显示出显着的抗真菌活性，与被视为标准药物的苯菌灵杀菌剂相近。对于最具活性的化合物和苯菌灵，已通过DFT计算和针对Fgb1蛋白的分子对接在实验性抗真菌活性与理论预测之间建立了相关性。
• Crystal structure, physicochemical, DFT, optical, keto-enol tautomerization, docking, and anti-diabetic studies of (Z)-pyrazol β-keto-enol derivative
  作者：Said Tighadouini、Othmane Roby、Salma Mortada、Zouhair Lakbaibi、Smaail Radi、Anas Al-Ali、My El Abbes Faouzi、Marilena Ferbinteanu、Yann Garcia、Nabil Al-Zaqri、Abdelkader Zarrouk、Ismail Warad

  DOI：10.1016/j.molstruc.2021.131308

  日期：2022.1

  The new (Z)-pyrazol β-keto-enol as model-molecule has been prepared in accepted high yield; the structure was investigated by X-ray single crystal diffraction (XRD) and Density Functional Theory (DFT) modeling. Several hydrogen bonds interactions were recorded experimentally via XRD and theoretically via Hirshfeld surface analysis (HSA) calculations. The recorded vibrational frequencies FT-IR were

  作为模型分子的新型 ( Z )-吡唑 β-酮-烯醇已以可接受的高产率制备；通过 X 射线单晶衍射 (XRD) 和密度泛函理论 (DFT) 建模研究了该结构。通过XRD实验记录了几个氢键相互作用，理论上通过Hirshfeld 表面分析 (HSA) 计算。记录的振动频率 FT-IR 进一步与计算的频率进行比较。已进行自然种群分析 (NPA)、马利肯原子电荷 (MAC) 和分子静电势 (MEP) 以完成这套理论工具。应用 HOMO/LUMO、态密度 (DOS) 和 TD-SCF/DFT 将这些量子参数与实验电子转移和直接光学活性进行比较。DFT计算、自然键轨道(NBO)分析和非共价相互作用(NCI)分析用于探索单质子酮-烯醇内迁移互变异构反应的机理。此外，还筛选了所需化合物的体外α-淀粉酶和α-葡萄糖苷酶抑制活性。标题化合物具有有效的抑制活性 α-葡萄糖苷酶，IC 50值为 72.20 ± 1.50