2,5-二甲基-1-苯基-1H-吡咯-3-羧酸乙酯 | 76546-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2,5-二甲基-1-苯基-1H-吡咯-3-羧酸乙酯
• 英文名称: ethyl 2,5-dimethyl-1-phenylpyrrole-3-carboxylate
• 英文别名: ethyl 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carboxylate
• CAS: 76546-68-4
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: LNBCSWPBLZPWKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  45-47 °C
• 沸点：
  360.9±37.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)
• 溶解度：
  3 [ug/mL]

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：
  0.27
• 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
• 海关编码：
  2933990090

SDS

Name:	Ethyl 2 5-dimethyl-1-phenyl-1h-pyrrole-3-carboxylate 95+% Material Safety Data Sheet
Synonym:
CAS:	76546-68-4

Section 1 - Chemical Product MSDS Name:Ethyl 2 5-dimethyl-1-phenyl-1h-pyrrole-3-carboxylate 95+% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
76546-68-4	Ethyl 2,5-dimethyl-1-phenyl-1H-pyrrole	95+%	unlisted

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

---

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.

---

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.

---

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.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

---

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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 76546-68-4: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 76546-68-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carboxylate - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

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# 76546-68-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 76546-68-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 76546-68-4 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,5-二甲基-1-苯基-1H-吡咯-3-羧酸乙酯 在 氯磺酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以13.3%的产率得到ethyl 2,5-dimethyl-1-phenyl-4-sulfamoyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  β-内酰胺酶抑制剂

  摘要：

  本发明的课题在于：提供一种具有β‑内酰胺酶抑制活性的化合物。通过具有平面性的5元环的特定位置被氨基磺酰基和羧基置换而成的化合物所代表的通式(1)所示的化合物来解决该课题。

  公开号：

  CN112165936A
• 作为产物：
  描述：

  ethyl 2-acetyl-4-bromopent-4-enoate 在 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 叔丁醇 、 苯 为溶剂， 反应 10.0h， 生成 2,5-二甲基-1-苯基-1H-吡咯-3-羧酸乙酯
  参考文献：
  名称：

  由2-（2-溴烯丙基）-1,3-二羰基化合物合成1,2,3,5-四取代的吡咯衍生物

  摘要：

  将2-（2-溴烯丙基）-1,3-二羰基化合物转化为β-烯氨基，β-肼基酸酯和酮，然后进行碱促进的环化反应，从而形成相应的1,2,3,5-四取代吡咯。1,2,4-和1,2,3,4-取代的吡咯也作为次要产物被分离出来。从2-（2-溴烯丙基）-环己烷-1，3-二酮开始，以高收率制备相应的四氢吲哚酮。

  DOI：

  10.1016/s0040-4020(02)01298-x

文献信息

• Indium-Catalyzed Synthesis of Furans and Pyrroles via Cyclization of α-Propargyl-β-keto Esters
  作者：Hayato Tsuji、Eiichi Nakamura、Ken-ichi Yamagata、Yasuyuki Ueda

  DOI：10.1055/s-0030-1259930

  日期：2011.4

  organic reactions involving carbonylgroups, 1 such as the Barbier reaction, 2 aldol reaction, 3 andHosomi–Sakurai reaction. 4 Indium can also activate C–Ctriple bonds to form new C–C bonds, because of its soft-ness, as reported by us 5 and others. 6 Formation of carbon–heteroatom bonds via activation of triple bonds has alsobeen reported. For instance, Tan et al. 7a described that 10mol% of InCl 3 promotes

  摘要：In(OTf) 3 或In(NTf 2 ) 3 可有效催化α-炔丙基-b-酮酯及其亚胺类似物的环异构化反应，分别生成三取代的呋喃和吡咯。该反应在少量催化剂存在下具有良好的官能团相容性。关键词：铟催化剂，酮酯，环化，呋喃，吡咯 铟试剂和催化剂的效用已被涉及羰基的有机反应广泛证明，1如Barbier反应，2羟醛反应，3和Hosomi-Sakurai反应。4 铟还可以激活 C-Ctriple 键以形成新的 C-C 键，因为它具有柔软性，正如我们 5 和其他人报道的那样。6 还报道了通过激活三键形成碳-杂原子键。例如，谭等人。图 7a 描述了 10mol% 的 InCl 3 通过串联反应促进呋喃衍生物的一锅合成，该反应涉及炔丙醇和 1,3-二羰基化合物（主要是 1,3-二酮）在回流氯气中的分子间缩合反应。苯。在此我们报告 In(OTf)
• 喹啉类衍生物及其用途
  申请人：苏州东南药业股份有限公司

  公开号：CN103664876B

  公开（公告）日：2016-04-20

  本发明公开了一类喹啉类衍生物及其用途，如式（1）所示结构的化合物或其药学上可接受的盐。本发明的化合物或其药学上可接受的盐可应用于制备预防或治疗癌症药物领域。
• An Efficient Procedure for the Synthesis of Polysubstituted Pyrroles in an Ionic Liquid
  作者：Yan-Hong He、Gang-Qiang Wang、Ke-Ling Xu、Zhi Guan

  DOI：10.1515/znb-2011-0212

  日期：2011.2.1

  1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, was used as a catalyst and reaction medium for the pyrrole synthesis, and a wide range of aliphatic, aromatic, heteroaromatic and carboxylic 1,4-diketones easily underwent condensations with aniline and ethylenediamine to form polysubstituted pyrroles. Sequential decarboxylation/Paal-Knorr pyrrole condensation was observed, which provides a new

  离子液体 1-丁基-3-甲基-咪唑硫酸氢盐 [bmim]HSO4 用作吡咯合成的催化剂和反应介质，以及广泛的脂肪族、芳香族、杂芳香族和羧基 1,4-二酮容易与苯胺和乙二胺缩合形成多取代的吡咯。观察到顺序脱羧/Paal-Knorr 吡咯缩合，这为从 1,4-二酮-2,3-二羧酸酯制备单酯吡咯提供了一种新的、简便的方法。图形摘要 一种在离子液体中合成多取代吡咯的有效方法
• Synthesis of pyrrolo[1,2-a]indoles: vilsmeier formylation of some 3-methylindol-2-yl ketones and 3(3-methylindol-2-yl)propenoic ester
  作者：Takawira C.-G. Kazembe、Deryck A. Taylor

  DOI：10.1016/0040-4020(80)80102-5

  日期：1980.1

  latter case, 2-carbethoxy-1-chloro-3-dimethylamino-9-methyl-3H-pyrrolo[1,2-a]indole (9b) was isolated as an intermediate. The structure of the pyrroloindolylidene acetaldehydes was proved by synthesis of the chromophore from 4-acetyl-3-methyl-1-phenyl-pyrrole-2-carboxylate (26). The preparation and behaviour of 1-phenylpyrrole-2,4- and 3,4-dicarboxylates, monomethylated in the pyrrole ring, is described

  3-甲基吲哚-2-基甲基酮与磷酰氯在二甲基甲酰胺中反应，得到3-氯-3（3-甲基吲哚-2-基），丙烯醛（4）。通过与3（3-甲基吲哚-2）的相同试剂反应生成2-Carbomethoxy-和2-carbethoxy-1-chloro-9H-pyrrolo [1,2-a] indol-9-次乙醛（10a和b）分别为（6- ）丙烯酸酯（7）和3（3-甲基吲哚-2-基）-3-氧代丙酸酯（2）。在后一种情况下，分离出2-碳乙氧基-1-氯-3-二甲基氨基-9-甲基-3H-吡咯并[1,2-a]吲哚（9b）作为中间体。由4-乙酰基-3-甲基-1-苯基-吡咯-2-羧酸酯合成发色团证明了吡咯并二亚甲基乙醛的结构（26）。描述了在吡咯环中单甲基化的1-苯基吡咯-2,4-和3,4-二羧酸酯的制备和行为。这些化合物是在寻找令人满意的途径合成与10a和b有关的化合物的起始原料的过程中制备的。这样的二酯的皂化作用是显着
• Discovery of novel Tetrahydrobenzo[ b ]thiophene and pyrrole based scaffolds as potent and selective CB2 receptor ligands: The structural elements controlling binding affinity, selectivity and functionality
  作者：Noha A. Osman、Alessia Ligresti、Christian D. Klein、Marco Allarà、Alessandro Rabbito、Vincenzo Di Marzo、Khaled A. Abouzid、Ashraf H. Abadi

  DOI：10.1016/j.ejmech.2016.07.012

  日期：2016.10

  binding affinity and CB2/CB1 subtype selectivity. Compound 19a and 19b from the pyrrole series exhibited the highest CB2 receptor affinity (Ki = 7.59 and 6.15 nM, respectively), as well as the highest CB2/CB1 subtype selectivity (∼70 and ∼200-fold, respectively). In addition, compound 6b from the tetrahydrobenzo[b]thiophene series presented the most potent and selective CB2 ligand in this series (Ki = 2

  基于CB2的疗法在治疗各种疾病（例如炎症，多发性硬化症，疼痛，免疫相关疾病，骨质疏松症和癌症）方面显示出强大的潜力，而不会引起CB1配体的典型神经行为副作用。因此，目前的研究活动是针对CB2选择性配体的开发。在本文中，报道了新颖的基于杂环的CB 2选择性化合物的合成。一组2,5-二烷基-1-苯基-1H-吡咯-3-羧酰胺，5-取代的-2-（酰基氨基）/（2-磺酰基氨基）-噻吩-3-羧酸盐和2-（酰基氨基）/（合成了2-磺酰基氨基）-四氢苯并[ b ]噻吩-3-羧酸盐。生物学结果表明化合物具有很高的CB2结合亲和力和CB2 / CB1亚型选择性。化合物19a吡咯系列中的 α和19b表现出最高的CB2受体亲和力（分别为K i = 7.59和6.15 nM）以及最高的CB2 / CB1亚型选择性（分别为〜70和〜200倍）。此外，来自四氢苯并[ b ]噻吩系列的化合物6b在该系列中表现出最有效和最具选择性的CB2配体（K