4-(2,5-二甲基-1H-吡咯-1-基)苯甲酸乙酯 | 5159-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-(2,5-二甲基-1H-吡咯-1-基)苯甲酸乙酯
• 英文名称: ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate
• 英文别名: ethyl 4-(2,5-dimethylpyrrol-1-yl)benzoate
• CAS: 5159-70-6
• 化学式: C₁₅H₁₇NO₂
• mdl: MFCD00022462
• 分子量: 243.305
• InChiKey: FIQJDBIRRVQTJN-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92°C
• 沸点：
  366.1±30.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.266
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

Name:	Ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate, 97% Material Safety Data Sheet
Synonym:
CAS:	5159-70-6

Section 1 - Chemical Product MSDS Name: Ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate, 97% Material Safety Data Sheet
Synonym:

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5159-70-6	Ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)b	97%	unlisted

+++++
Hazard Symbols: 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# 5159-70-6: 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: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 88 - 90 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: C15H17NO2
Molecular Weight: 243

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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, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 5159-70-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate - 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# 5159-70-6: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 5159-70-6 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 5159-70-6 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 3/21/2003 Revision #0 Date: Original. The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(2,5-二甲基-1H-吡咯-1-基)苯甲酸乙酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 N-(benzhydrylideneamino)-4-(2,5-dimethylpyrrol-1-yl)benzamide
  参考文献：
  名称：

  合成新的4-（2,5-二甲基吡咯-1-基）/ 4-吡咯-1-基苯甲酰肼类似物和一些衍生的恶二唑，三唑和吡咯环系统：一类新型的潜在抗菌剂，抗真菌剂和抗结核剂

  摘要：

  摘要一系列4-（2,5-二甲基吡咯-1-基）/ 4-吡咯-1-基苯甲酸酰肼类似物，一些衍生的1,3,4-恶二唑，5-取代的-4-氨基-1,2合成了高产率的1，4-三唑啉-3-硫酮和2，5-二甲基吡咯，并通过IR，1 H NMR，13 C NMR，质谱和元素分析确定了这些化合物的结构。通过肉汤稀释法评价这些化合物对结核分枝杆菌H 37 Rv菌株的初步体外抗菌，抗真菌和抗结核活性。这些化合物中的十二种显示出良好的抗菌活性，最小抑菌浓度（MIC）值为1-4μgmL -1。几种化合物4，8D，9，12C - d和12F - ħ体外抗结核活性显示出良好的与MIC值1-2微克毫升-1。此外，还使用MTT测定法评估了一些标题化合物对哺乳动物Vero细胞系和A 549（肺腺癌）细胞系的细胞毒活性（IC 50）。结果表明，这些化合物在非细胞毒性浓度下具有抗结核活性。 图形概要描述了一系列新型吡咯衍生物的合成，光谱研究以及抗菌，抗真菌和抗结核活性

  DOI：

  10.1007/s00044-012-0112-0
• 作为产物：
  描述：

  对氨基苯甲酸 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 4-(2,5-二甲基-1H-吡咯-1-基)苯甲酸乙酯
  参考文献：
  名称：

  新型吡咯衍生物作为抗结核药的合成，表征，生物学活性和3D-QSAR研究

  摘要：

  摘要设计，合成了一系列新的吡咯衍生物，并阐明了它们的结构，并使用微孔板阿拉玛蓝法评估了其对结核分枝杆菌H 37 Rv的抗结核活性以及对金黄色葡萄球菌，枯草芽孢杆菌，肺炎克雷伯菌的抗菌活性，以及通过肉汤微稀释法测定的大肠杆菌。结构活性关系和3D-QSAR分析已通过拓扑异构体比较分子场分析（CoMFA）进行。使用42个训练集和8个活性化合物的测试集来开发显示交叉验证相关系数（q 2）为0.815，预测标准误差为0.36，非交叉验证相关系数（r 2）为0.973，六项估计的标准误差为0.14。 图形概要合成; 频谱和3D-QSAR研究；描述了一系列新颖的吡咯衍生物的抗细菌，抗结核和细胞毒性活性。

  DOI：

  10.1007/s00044-013-0709-y

文献信息

• Synthesis, characterization and antitubercular activities of novel pyrrolyl hydrazones and their Cu-complexes
  作者：Shrinivas D. Joshi、Devendra Kumar、Sheshagiri R. Dixit、Nageshwar Tigadi、Uttam A. More、Christian Lherbet、Tejraj M. Aminabhavi、Kap Seung Yang

  DOI：10.1016/j.ejmech.2016.05.025

  日期：2016.10

  Novel pyrrolyl hydrazones and their copper complexes have been synthesized and characterized using analytical and spectral techniques to show the tetrahedral geometry for Cu(II) complexes. Biological activities of hydrazones have been assessed to understand the role of metal ion on their biological activity and the effect of pyrrolyl hydrazones. In vitro antitubercular activity against Mycobacterium

  合成了新型吡咯基hydr及其铜配合物，并使用分析和光谱技术对其进行了表征，以显示Cu（II）配合物的四面体几何形状。评估了hydr的生物活性，以了解金属离子对其生物学活性的作用以及吡咯基的作用。对金属配合物（13b和13r的结核分枝杆菌）的体外抗结核活性）表现出最高的抗结核活性，非常接近利福平（0.4μg/ mL），MIC为0.8μg/ mL。所有其他化合物均显示出良好的活性，MIC值为1.6至100μg/ mL。配体及其配合物的抑制值的比较研究表明，配合物的抗菌活性高于配体。一些化合物对InhA具有良好的活性，尤其是化合物12r，13b和13r甚至在5μM时仍显示出与酶的60％以上的结合（显示出高达2.4μM的良好IC50）。大多数活性分子对人肺癌细胞系A549的细胞毒性非常小。已经进行了对接和3D-QSAR研究，以提供有关此类化合物作用机理的一些见解。
• Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents
  作者：Uttam A. More、Shrinivas D. Joshi、Tejraj M. Aminabhavi、Andanappa K. Gadad、Mallikarjuna N. Nadagouda、Venkatrao H. Kulkarni

  DOI：10.1016/j.ejmech.2013.11.004

  日期：2014.1

  In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole

  为了开发抗结核分枝杆菌的先导化合物，已合成和筛选了一系列针对必需的烯酰-ACP还原酶的52种新颖的吡咯肼衍生物。采用表面对接法研究了化合物在烯酰-ACP还原酶活性位点的结合方式。结合模型表明吡咯和InhA酶之间有一个或两个氢键相互作用。高活性化合物5r（MIC 0.2μg/ mL）显示与Tyr158和NAD +的氢键相互作用以与配体PT70和三氯生相同的方式。就整体统计而言，通过数据库对齐生成的CoMFA和CoMSIA模型是最好的。CoMFA和CoMSIA模型的预测能力是使用13种化合物的测试集确定的，其预测相关系数（r pred 2）分别为0.896和0.930。
• Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst
  作者：Pavel Ryabchuk、Thomas Leischner、Carsten Kreyenschulte、Anke Spannenberg、Kathrin Junge、Matthias Beller

  DOI：10.1002/anie.202007613

  日期：2020.10.12

  A bifunctional 3d‐metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr‐C@SiO2‐L is obtained by pyrolysis of a cobalt‐impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson‐Kass condensation provides

  提出了一种用于从硝基芳烃级联合成多种吡咯的双功能3d金属催化剂。最佳催化体系Co/NGr-C@SiO 2 -L是通过热解钴浸渍复合材料并随后进行选择性浸出而获得的。在这种材料的存在下，容易获得的硝基芳烃的（转移）氢化和随后的 Paal-Knorr/Clauson-Kass 缩合可使用二氢、甲酸或 CO/H 2 O混合物（WGSR条件）作为还原剂。除了有利的步骤经济性之外，这种简单的多米诺骨牌工艺不需要任何溶剂或外部助催化剂。该方法的一般合成效用在各种功能化底物上得到了证明，包括生物活性和药学相关化合物的制备，例如（+）-异沙莫坦。
• Tapping into the antitubercular potential of 2,5-dimethylpyrroles: A structure-activity relationship interrogation
  作者：Dorothy Semenya、Meir Touitou、Domiziana Masci、Camila Maringolo Ribeiro、Fernando Rogerio Pavan、Guilherme Felipe Dos Santos Fernandes、Beatrice Gianibbi、Fabrizio Manetti、Daniele Castagnolo

  DOI：10.1016/j.ejmech.2022.114404

  日期：2022.7

  An exploration of the chemical space around a 2,5-dimethylpyrrole scaffold of antitubercular hit compound 1 has led to the identification of new derivatives active against Mycobacterium tuberculosis and multidrug-resistant clinical isolates. Analogues incorporating a cyclohexanemethyl group on the methyleneamine side chain at C3 of the pyrrole core, including 5n and 5q, exhibited potent inhibitory

  对抗结核打击化合物1的 2,5-二甲基吡咯支架周围化学空间的探索导致鉴定出对结核分枝杆菌和耐多药临床分离株具有活性的新衍生物。在吡咯核心 C3 的亚甲基胺侧链上加入环己烷甲基的类似物，包括5n和5q ，对结核分枝杆菌表现出有效的抑制作用菌株，证实了该部分对其抗分枝杆菌活性的重要性。此外，选定的衍生物对人肺成纤维细胞和/或鼠巨噬细胞显示出有希望的细胞毒性特征，证明可有效抑制细胞内分枝杆菌的生长，并引起杀菌作用或与1相当的抑菌活性。计算研究表明，新化合物与推定的靶标 MmpL3 的结合方式与已知抑制剂 BM212 和 SQ109 的结合方式相似。
• Silver halide photographic light-sensitive material
  申请人：Fuji Photo Film Co., Ltd.

  公开号：US05296344A1

  公开（公告）日：1994-03-22

  There is disclosed a silver halide photographic light-sensitive material containing a dye which colors a specific layer in the light-sensitive material and furthermore is quickly decolored and/or eluted during a development processing. The light-sensitive material contains at least one compound represented by the following formula (1), (2) or (3): ##STR1## wherein R.sup.11 represents a hydrogen atom, an alkyl group, an aryl group, --COOR.sup.16, or --CONR.sup.16 R.sup.17 ; R.sup.12, R.sup.13 and R.sup.14 each represents a hydrogen atom, an alkyl group, and an aryl group; R.sup.15 represents a hydrogen atom, an alkyl group, an aryl group, or an amino group; R.sup.13 and R.sup.14 may be combined to form a 6-membered ring; and R.sup.16 and R.sup.17 each represents a hydrogen atom, an alkyl group, and an aryl group; provided that the compound represented by formula (1) does not have a carboxy group or a salt thereof as a substituent; ##STR2## wherein R.sup.1 represents an alkyl group or an aryl group; R.sup.2 represents an alkyl group, an aryl group or a hydrogen atom; R.sup.3 represents a hydrogen atom or an alkyl group; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, --OR.sup.21, --NR.sup.21 R.sup.22, --N(R.sup.21)SO.sub.2 R.sup.22, --N(R.sup.21)COR.sup.22, and --COOR.sup.21 ; and R.sup.21 and R.sup.22 each represents a hydrogen atom, an alkyl group and an aryl group; provided that the compound represented by formula (2) does not have a carboxy group or a salt thereof as a substituent; ##STR3## wherein R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each represents the same groups as those defined for R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 in formula (2); X represents --SO.sub.2 NH--, --SO.sub.2 NHCO--, --CONHCO--, or --SO.sub.2 NHSO.sub.2 --; R.sup.8 represents an alkyl group, an aryl group or a heterocyclic group; R.sup.9 represents a hydrogen atom, an alkyl group, an aryl group, --OR.sup.23, --NR.sup.23 R.sup.24, --N(R.sup.23)COR.sup.24, or --COOR.sup.23 ; and R.sup.23 and R.sup.24 each represents a hydrogen atom, an alkyl group and an aryl group; provided that the compound represented by formula (3) does not have a carboxy group or a salt thereof as a substituent. There is also disclosed a methine dye represented by the above formula (1), (2) or (3).

  公开了一种含有染料的银卤化物感光材料，该染料着色于感光材料中的特定层，并且在显影处理期间迅速褪色和/或析出。该感光材料包含至少一种由以下公式（1）、（2）或（3）表示的化合物： ##STR1## 其中R.sup.11表示氢原子、烷基、芳基、-COOR.sup.16或-CONR.sup.16R.sup.17；R.sup.12、R.sup.13和R.sup.14分别表示氢原子、烷基和芳基；R.sup.15表示氢原子、烷基、芳基或氨基；R.sup.13和R.sup.14可以结合形成6元环；R.sup.16和R.sup.17各表示氢原子、烷基和芳基；但由公式（1）表示的化合物不具有羧基或其盐作为取代基； ##STR2## 其中R.sup.1表示烷基或芳基；R.sup.2表示烷基、芳基或氢原子；R.sup.3表示氢原子或烷基；R.sup.4、R.sup.5、R.sup.6和R.sup.7分别表示氢原子、烷基、芳基、卤素原子、-OR.sup.21、-NR.sup.21R.sup.22、-N(R.sup.21)SO.sub.2R.sup.22、-N(R.sup.21)COR.sup.22和-COOR.sup.21；R.sup.21和R.sup.22各表示氢原子、烷基和芳基；但由公式（2）表示的化合物不具有羧基或其盐作为取代基； ##STR3## 其中R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6和R.sup.7分别表示与公式（2）中定义的R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6和R.sup.7相同的基团；X表示-SO.sub.2NH-、-SO.sub.2NHCO-、-CONHCO-或-SO.sub.2NHSO.sub.2-；R.sup.8表示烷基、芳基或杂环基；R.sup.9表示氢原子、烷基、芳基、-OR.sup.23、-NR.sup.23R.sup.24、-N(R.sup.23)COR.sup.24或-COOR.sup.23；R.sup.23和R.sup.24各表示氢原子、烷基和芳基；但由公式（3）表示的化合物不具有羧基或其盐作为取代基。还公开了一种由上述公式（1）、（2）或（3）表示的甲烷染料。