1,2,5-三甲基-1H-吡咯-3-羧酸甲酯 | 14186-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1,2,5-三甲基-1H-吡咯-3-羧酸甲酯
• 英文名称: 1,2,5-trimethyl-1H-pyrrole-3-carboxylic acid methyl ester
• 英文别名: methyl 1,2,5-trimethyl-1H-pyrrole-3-carboxylate；methyl 1,2,5-trimethylpyrrole-3-carboxylate；1,2,5-trimethyl-pyrrole-3-carboxylic acid methyl ester；1,2,5-Trimethyl-3-carboxy-pyrrolmethylester；Methyl-1,2,5-trimethylpyrrol-3-carboxylat
• CAS: 14186-50-6
• 化学式: C₉H₁₃NO₂
• mdl: MFCD00203867
• 分子量: 167.208
• InChiKey: VRUCCWQGKPXNMI-UHFFFAOYSA-N

物化性质

• 熔点：
  110-115
• 沸点：
  250.1±35.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 储存条件：
  常温下应密闭避光保存，并保持干燥通风的环境。

SDS

Name:	Methyl 1 2 5-trimethyl-1h-pyrrole-3-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	14186-50-6

Section 1 - Chemical Product MSDS Name:Methyl 1 2 5-trimethyl-1h-pyrrole-3-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14186-50-6	Methyl 1,2,5-trimethyl-1H-pyrrole-3-ca	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 14186-50-6: 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: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 110 - 115 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: C9H13NO2
Molecular Weight: 167

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14186-50-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 1,2,5-trimethyl-1H-pyrrole-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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 14186-50-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14186-50-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14186-50-6 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

反应信息

• 作为反应物：
  描述：

  1,2,5-三甲基-1H-吡咯-3-羧酸甲酯 在 氯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 4-((3-((3-chloro-4-fluorophenyl)carbamoyl)piperidin-1-yl)sulfonyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  N-磺酰基杂环衍生物及其制药用途

  摘要：

  本发明公开了N‑磺酰基杂环衍生物及其制药用途。该N‑磺酰基杂环衍生物的结构如式I所示。实验表明，本发明提供的化合物能够有效抑制乙型肝炎病毒核心蛋白组装和乙型肝炎病毒的复制。本发明提供的化合物在制备乙型肝炎病毒核心蛋白组装抑制剂、抗乙型肝炎病毒的药物、以及预防和/或治疗乙型肝炎病毒感染相关疾病(例如乙型肝炎、肝硬化、肝癌)的药物中具有广阔的应用前景。

  公开号：

  CN112679489B
• 作为产物：
  描述：

  1,4-dimethyl-3-trimethylsilanyl-azetidin-2-one 在 sodium 、 lithium diisopropyl amide 作用下， 反应 0.55h， 生成 1,2,5-三甲基-1H-吡咯-3-羧酸甲酯
  参考文献：
  名称：

  Thielmann, Marion; Winterfeldt, Ekkehard, Heterocycles, 1984, vol. 22, # 5, p. 1161 - 1167

  摘要：

  DOI：

文献信息

• Dual C–F, C–H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls
  作者：Sameera Senaweera、Jimmie D. Weaver

  DOI：10.1021/jacs.5b13450

  日期：2016.3.2

  An alternative approach to selective fluorination of biaryls is to couple an arene that already possesses C-F bonds in the desired location. This strategy has been regularly utilized and relies heavily on traditional cross-coupling strategies that employ organometallics and halides (or pseudohalides) in order to achieve the coupling. Herein we report conditions for the photocatalytic coupling via

  多氟化联芳基化合物的合成具有挑战性，但仍是一类重要的分子。由于与选择性氟化相关的困难，这类分子代表了一项艰巨的合成挑战。选择性氟化联芳基的另一种方法是在所需位置偶联已经具有 CF 键的芳烃。该策略已被经常使用，并且在很大程度上依赖于采用有机金属和卤化物（或伪卤化物）以实现耦合的传统交叉耦合策略。在此，我们报告了通过全氟芳烃的 CF 键和其他芳烃的 CH 键的直接官能化进行光催化偶联的条件，以提供获得多氟化联芳基化合物的便捷途径。温和的条件和良好的官能团耐受性使范围广泛，包括获得碱性杂环的反 Minisci 产物。最后，我们通过光催化和 SNAr 化学的协同使用，利用高氟含量系统地构建包含 2 到 5 个 Cyl-F 键的复杂联芳基，证明了 CF 功能化方法的价值。
• Intermolecular 1,3-dipolar cycloadditions of müchnones with acetylenic dipolarophiles: Sorting out the regioselectivity
  作者：Brian P. Coppola、Mark C. Noe、David J. Schwartz、Robert L. Abdon、Barry M. Trost

  DOI：10.1016/s0040-4020(01)80739-0

  日期：1994.4

  A series of 1,3-dipolar cycloadditions of münchnones with acetylenic dipolarophiles was studied, wherein factors related to regioselectivity were investigated. The results from münchnones with electronically divergent thioaryl substituents compared with others bearing alkyl substituents suggest that an unsymmetrical transition state structure, rather than FMO perturbation, plays a significant role

  研究了一系列的慕尼黑1,3-偶极环加成与炔属双极亲和性，研究了与区域选择性有关的因素。具有电子发散的硫代芳基取代基的慕尼黑人与其他带有烷基取代基的慕尼黑人的结果表明，不对称的过渡态结构而不是FMO扰动在区域选择中起着重要作用。但是，如果日蚀相互作用排除了高度不对称的过渡态，那么最小化空间相互作用就变得很重要。一对互补取代的münchnones，仅同位素标记的位置不同，建立了中离子杂环的内在对称电子性质。
• Reaction of 2,5-dimethylpyrroles with quinones. Synthesis of new pyrrolylquinones
  作者：Dyes Claude Lion、Richard Baudry、Mir Hedayatullah、Louis Da Conceiçlato、Sylvie Genard、Jean Maignan

  DOI：10.1002/jhet.5570390118

  日期：2002.1

  The reaction of 1,4-naphthoquinone (1) with 2,5-dimethylpyrroles (7a-7d) gives only 3-(1,4-naphtho-quinonyl)-2,5-dimethylpyrroles. Extending the reaction to other quinones: 5-hydroxy-1,4-naphthoquinone (2), 1,2-naphthoquinone (3), quinoline-5,8-dione (4) and quinoxaline-5,8-dione (5), of which nothing was known, allows the synthesis of new pyrrolylquinones.

  1,4-萘醌（1）与2,5-二甲基吡咯（7a-7d）的反应仅产生3-（1,4-萘醌基）-2,5-二甲基吡咯。将反应扩展至其他醌：5-羟基-1,4-萘醌（2），1,2-萘醌（3），喹啉5,8-二酮（4）和喹喔啉-5,8-二酮（5） ，其中什么都不知道，可以合成新的吡咯基醌。
• Synthesis and evaluation of N-sulfonylpiperidine-3-carboxamide derivatives as capsid assembly modulators inhibiting HBV in vitro and in HBV-transgenic mice
  作者：Jiaxin Yin、Zhongqi Feng、Zhi Li、Jieli Hu、Yuan Hu、Xuefei Cai、Hui Zhou、Kai Wang、Ni Tang、Ailong Huang、Luyi Huang

  DOI：10.1016/j.ejmech.2023.115141

  日期：2023.3

  The hepatitis B virus (HBV) capsid assembly modulators (CAMs) have been developed as effective anti-HBV agents in the treatment of chronic HBV infection by targeting the HBV core protein and inducing the formation of aberrant or morphologically normal capsid. However, some CAMs have been observed adverse events such as ALT flares and rash. Therefore, finding new CAMs is of great importance. In this

  乙型肝炎病毒 (HBV) 衣壳组装调节剂 (CAM) 已被开发为有效的抗 HBV 药物，通过靶向 HBV 核心蛋白并诱导异常或形态正常衣壳的形成来治疗慢性 HBV 感染。然而，一些 CAM 已观察到不良事件，例如 ALT 耀斑和皮疹。因此，寻找新的 CAM 非常重要。在本报告中，我们合成了 N-磺酰基哌啶-3-甲酰胺 (SPC) 衍生物并评估了它们的抗 HBV 活性。在 SPC 衍生物中，化合物 C-49 显着抑制 HepAD38、HepG2-HBV1.3 和 HepG2-NTCP 细胞中的 HBV 复制。此外，用 C-49 治疗 12 天在 HBV 转基因小鼠中表现出有效的抗 HBV 活性（100 mg/kg；血清 HBV DNA 降低 2.42 对数），而没有明显的肝毒性。
• 4-ACYLAMINOPYRAZOLE DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP1329160A2

  公开（公告）日：2003-07-23

  A 4-acylaminopyrazole derivative represented by the following general formula: wherein R1 is a hydrogen atom, an optionally substituted C1-C16 alkyl group or the like,    R2 and R3 are independently a hydrogen atom, a halogen atom, an optionally substituted C1-C6 alkyl group or the like, R4 is a hydrogen atom, a C1-C6 alkyl group or a cyano group, Z is an oxygen atom or a sulfur atom, Ar is an optionally substituted C6-C14 aryl group or an optionally substituted 5-6 membered unsaturated heterocyclic group, B is a hydrogen atom, a halogen atom, an optionally substituted C1-C16 alkyl group or the like.

  由以下通式代表的 4-酰氨基吡唑衍生物： 其中 R1 是氢原子、任选取代的 C1-C16 烷基或类似基团、 R2 和 R3 独立地为氢原子、卤素原子、任选取代的 C1-C6 烷基或类似基团、 R4 是氢原子、C1-C6 烷基或氰基、 Z 是氧原子或硫原子、 Ar 是任选取代的 C6-C14 芳基或任选取代的 5-6 位元不饱和杂环基团、 B 是氢原子、卤素原子、任选取代的 C1-C16 烷基或类似基团。