3-乙酰基-2,4-二甲基-5-乙氧羰基吡咯 | 2386-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙酰基-2,4-二甲基-5-乙氧羰基吡咯
• 中文别名: 4-乙酰基-3,5-二甲基-1H-吡咯-2-甲酸乙酯；2,4-二甲基-3-乙酰基-5-乙酰氧基吡咯；3-乙酰-2,4-二甲基-5乙氧羰基吡咯；2,4-二甲基-3-乙酰基-5-乙酸基吡咯
• 英文名称: ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate
• 英文别名: ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 2386-26-7
• 化学式: C₁₁H₁₅NO₃
• mdl: MFCD00022373
• 分子量: 209.245
• InChiKey: ALRDOFWBPAZOCW-UHFFFAOYSA-N

物化性质

• 熔点：
  143 °C
• 沸点：
  348.6°C (rough estimate)
• 密度：
  1.1547 (rough estimate)
• 稳定性/保质期：
  避免让氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S22,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 储存条件：
  请将容器密封，并存放在干燥、阴凉的地方。

SDS

Name:	Ethyl 4-acetyl-3 5-dimethyl-1h-pyrrole-2-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	2386-26-7

Section 1 - Chemical Product MSDS Name:Ethyl 4-acetyl-3 5-dimethyl-1h-pyrrole-2-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2386-26-7	Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole	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# 2386-26-7: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 139 - 141 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: C11H15NO3
Molecular Weight: 209

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
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# 2386-26-7: UX9370900 LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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# 2386-26-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2386-26-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2386-26-7 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：

  3-乙酰基-2,4-二甲基-5-乙氧羰基吡咯 在 磺酰氯 、 Montmorillonite K₁₀ clay 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 3-(3'-acetyl-5'-ethoxycarbonyl-4'-methylpyrrol-2'-ylmethyl)indole
  参考文献：
  名称：

  Chunchatprasert, Laddawan; Rao, K. R. Nagaraja; Shannon, Patrick V. R., Journal of the Chemical Society. Perkin transactions I, 1992, # 14, p. 1779 - 1784

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(1-chloro-vinyl)-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester 生成 3-乙酰基-2,4-二甲基-5-乙氧羰基吡咯
  参考文献：
  名称：

  KOZHICH D. T.; AKIMENKO L. V.; MIRONOV A. F.; EVSTIGNEEVA R. P., ZH. ORGAN. XIMII, 1977, 13, HO 12, 2604-2608

  摘要：

  DOI：

文献信息

• Total Synthesis of Hematoporphyrin and Protoporphyrin: A Conceptually New Approach
  作者：Pierre Martin、Markus Mueller、Dietmar Flubacher、Andreas Boudier、Hans-Ulrich Blaser、Dirk Spielvogel

  DOI：10.1021/op100036c

  日期：2010.7.16

  The total synthesis of protoporphyrin IX and its disodium salt using a new alternative method to the classical MacDonald condensation is reported. The key step is the reaction of the new unsymmetrical diiodo dipyrrylmethane 1 with the known dipyrrylmethane 2. Coupling of the two fragments leads directly to porphyrin 3 without the need of an oxidizing agent. The new methodology is well suited for the

  据报道，使用一种经典的麦克唐纳缩合的新方法，原卟啉phy及其二钠盐的全合成。关键步骤是新的不对称二碘二吡咯基甲烷1与已知的二吡咯基甲烷2的反应。两个片段的偶联直接导致卟啉3，而无需氧化剂。该新方法非常适合以高质量进行多100 g规模的原卟啉IX衍生物的合成，而无需进行色谱分离。此外，这些制剂完全不含任何动物来源的污染物，这代表了原卟啉IX衍生物生产中的真正改进。
• Process For Preparing Porphyrin Derivatives, Such As Protoporphyrin (IX) And Synthesis Intermediates
  申请人：Martin Pierre

  公开号：US20080242857A1

  公开（公告）日：2008-10-02

  The present invention relates to a process for preparing a porphyrin of formula (I), optionally in the form of a salt with an alkali metal and/or in the form of a metal complex: in which: R and R′ are as defined in claim 1 , comprising: a step of condensation, in an acidic medium, between a dipyrromethane of formula (II): in which R′b is as defined above for (I), and a dipyrromethane of formula (III): in which R″ is as defined in claim 1 , and also the compounds of formula (III).

  本发明涉及一种制备公式（I）的卟啉的方法，可选地以碱金属的盐形式和/或金属配合物的形式存在： 其中： R和R′如权利要求1中定义的那样， 包括： 在酸性介质中，通过公式（II）的二吡咯甲烷和公式（III）的二吡咯甲烷之间的缩合步骤： 其中R′b如上述（I）中定义的那样， 以及公式（III）的化合物。
• Total Synthesis of Hematoporphyrin and Protoporphyrin; a Conceptually New Approach
  作者：Pierre Martin、Markus Müller、Dietmar Flubacher、Andreas Boudier、Dirk Spielvogel

  DOI：10.2533/chimia.2013.204

  日期：——

  The total synthesis of protoporphyrin IX and its disodium salt using a new alternative method to the classical MacDonald condensation is reported. The key step is the reaction of the new unsymmetrical diiodo dipyrrylmethane 1 with the known dipyrrylmethane 2. Coupling of the two fragments leads directly to porphyrin 3 without the need of an oxidizing agent. The new methodology is well suited for the synthesis of protoporphyrin IX derivatives on a multi-100 g scale in good quality without the need for chromatography. Furthermore, these preparations are completely free of any contaminant of animal origin, which represents a real improvement in the manufacturing of protoporphyrin IX derivatives.

  原文翻译如下： 报道了使用一种新的替代方法合成原卟啉IX及其二钠盐的总合成，该方法取代了传统的MacDonald缩合反应。关键步骤是将新的非对称二碘二吡咯甲烷1与已知的二吡咯甲烷2反应。这两个片段的偶联直接导致卟啉3的形成，无需氧化剂。这种新方法非常适合在多100克的规模上合成高质量的原卟啉IX衍生物，而无需进行色谱分离。此外，这些制备完全不含任何动物来源的污染物，这在原卟啉IX衍生物的制造中代表了一个真正的改进。
• Design synthesis and anti-proliferative activity of some new coumarin substituted hydrazide–hydrazone derivatives
  作者：Nongnaphat Duangdee、Wiratchanee Mahavorasirikul、Saisuree Prateeptongkum

  DOI：10.1007/s12039-020-01767-4

  日期：2020.12

  hydrazide–hydrazone derivatives. Unfortunately, all test compounds, as well as doxorubicin, showed no cytotoxicity toward drug-resistant cell line, Caco-2. Our preliminary results indicated that coumarin hydrazide–hydrazone derivatives could be exploited as leading structures for further anticancer-drug development. Graphic abstract Synthesis of coumarin substituted hydrazide-hydrazone derivatives

  摘要 设计，合成和评估了一系列21种香豆素酰肼-hydr衍生物，并在体外以25μg/ mL的浓度评估48 h对肝癌（HepG2）细胞系的潜在细胞毒性作用。然后，从21种化合物中筛选出7种细胞存活率低于60％的化合物，以评估其对肝癌（HepG2），乳腺癌（SKBR-3）和人结肠癌（Caco-2）细胞的体外抗增殖活性线。在测试化合物中，5g，6d和6f对Hep-G2和SKBR-3细胞系均显示出有效的活性。更重要的是，具有4-溴苯基部分的化合物6d对IC 50表现出对Hep-G2细胞系的最佳细胞毒性活性值2.84±0.48μg/ mL，与标准阿霉素相当（IC 50  = 2.11±0.13μg/ mL）。此外， 与其他经测试的香豆素酰肼-hydr衍生物相比，具有4-甲氧基苯基部分的化合物6f对SKBR-3细胞系表现出最强的活性（IC 50 = 2.34±0.68μg/ mL）。不幸的是，所有测试
• Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy
  作者：Bo Kong、Zhaohong Zhu、Hongmei Li、Qianqian Hong、Cong Wang、Yu Ma、Wan Zheng、Fei Jiang、Zhimin Zhang、Ting Ran、Yuanyuan Bian、Na Yang、Tao Lu、Jiapeng Zhu、Weifang Tang、Yadong Chen

  DOI：10.1016/j.ejmech.2021.113953

  日期：2022.1

  modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic

  作为表观遗传阅读器，溴结构域和末端外结构域 (BET) 家族蛋白与组蛋白中的乙酰化赖氨酸残基结合并募集蛋白质复合物以促进转录起始和延伸。通过小分子抑制剂抑制 BET 溴结构域已成为一种有前途的癌症治疗策略。在这里，我们描述了我们为发现一系列新的 1-(5-(1 H -benzo[ d ]imidazole-2-yl)-2,4-dimethyl-1 H -pyrrol-3-yl)ethan 所做的努力-1-one 衍生物作为 BET 抑制剂。密集的结构修饰导致化合物35f被鉴定为对 BET 家族蛋白具有选择性的最活跃的 BET BRD4 抑制剂。进一步的生物学研究表明，化合物35f通过降低c-Myc等细胞周期和细胞凋亡相关蛋白的表达，使细胞周期停滞在G 0 /G 1期，诱导细胞凋亡。更重要的是，化合物35f在 MV4-11 小鼠异种移植模型中显示出良好的药代动力学特性和抗肿瘤功效，具有可接受的耐受性。这些结果表明，BET

表征谱图