2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-甲酸乙酯 | 4815-29-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-甲酸乙酯
• 中文别名: 2-氨基环戊并[B!噻吩-3-甲酸乙酯；2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-羧酸乙酯
• 英文名称: ethyl 2-amino-4H,5H,6H-cyclopentenothiophene-3-carboxylate
• 英文别名: ethyl 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate
• CAS: 4815-29-6
• 化学式: C₁₀H₁₃NO₂S
• mdl: MFCD00102063
• 分子量: 211.285
• InChiKey: BOJXCJDYZJSPMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  90-94 °C
• 沸点：
  386.8±42.0 °C(Predicted)
• 密度：
  1.2079 (rough estimate)
• 保留指数：
  1812

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn,Xi
• 安全说明：
  S22
• 危险类别码：
  R20/22
• 海关编码：
  2934999090
• 储存条件：
  存于2-8°C环境中，应避免光照，保持干燥并密封。

SDS

Name:	Ethyl 2-aminocyclopenta[b]thiophene-3-carboxylate 99+% Material Safety Data Sheet
Synonym:	None
CAS:	4815-29-6

Section 1 - Chemical Product MSDS Name:Ethyl 2-aminocyclopenta[b]thiophene-3-carboxylate 99+% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4815-29-6	Ethyl 2-aminocyclopenta[b]thiophene-3-	99+	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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 immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 4815-29-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin. Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: pale yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 90.00 - 92.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: soluble in methanol and ethanol
Specific Gravity/Density: Not available.
Molecular Formula: C10H13NO2S
Molecular Weight: 211.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4815-29-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-aminocyclopenta[b]thiophene-3-carb oxylate - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 4815-29-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4815-29-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4815-29-6 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：

  2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-甲酸乙酯 在 potassium tert-butylate 草酰氯 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.01h， 生成 2-(4-chloro-phenyl)-4-hydrazino-5,6,7-trihydrocyclopenta[b]thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  一些新型三唑并噻吩并嘧啶的合成和抗菌活性。

  摘要：

  一系列新颖的5-取代的1,2,4-三唑[4,3-c] 8,9,10-三氢环戊/ 8,9,10,11,12-五氢环庚[b]噻吩并[3，已经合成了2-e]嘧啶-3-硫酮。通过加热2-取代-5，制备中间体4-氯-2-取代-5,6,7-三氢环戊/ 5,6,7,8,9-五氢环庚[b]噻吩并[2,3-d]嘧啶。 ，6,7-三氢环戊5 / 5,6,7,8,9-五氢环庚[b]噻吩并[2,3-d]嘧啶-4 [3H]-与草酰氯。噻吩并[2,3-d]嘧啶-4 [3H]-是通过新颖的，微波辅助的，无溶剂的合成路线在迄今文献中从未报道过的由噻吩的邻氨基酯制备的碱性条件下制备的。无需进一步纯化即可将氯代衍生物肼化，得到2-取代的4-肼基-5,6,7-三氢环戊5 / 5,6,7,8,9-五氢环庚[b] thieno [2,3-d]嘧啶类。这些化合物用二硫化碳环化，以定量收率得到标题化合物。使用氨苄青霉素作为标准品，针对

  DOI：

  10.1248/cpb.55.557
• 作为产物：
  描述：

  在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-甲酸乙酯
  参考文献：
  名称：

  使用 Gewald 反应在离子液相载体上合成 2-氨基噻吩

  摘要：

  摘要 本文首次报道了使用任务特异性离子液体作为 Gewald 合成 2-氨基噻吩的可溶性支持物。该合成方法简单高效，产品收率高，纯度高，无需色谱纯化。

  DOI：

  10.1080/00397910600588819

文献信息

• 2-(3,4-Dihydro-4-Oxothieno[2,3-d]pyrimidin-2-ylthio) Acetamides as a New Class of Falcipain-2 Inhibitors. 3. Design, Synthesis and Biological Evaluation
  作者：Jin Zhu、Tong Chen、Jie Liu、Ruoqun Ma、Weiqiang Lu、Jin Huang、Honglin Li、Jian Li、Hualiang Jiang

  DOI：10.3390/molecules14020785

  日期：——

  The cysteine protease falcipain-2 (FP-2) of Plasmodium falciparum is a principal cysteine protease and an essential hemoglobinase of erythrocytic P. falciparum trophozoites, making it become an attractive target enzyme for developing anti-malarial drugs. In this study, a series of novel small molecule FP-2 inhibitors have been designed and synthesized based on compound 1, which was identified by using structure-based virtual screening in conjunction with an enzyme inhibition assay. All compounds showed high inhibitory effect against FP-2 with IC50s of 1.46-11.38 μM, and the inhibitory activity of compound 2a was ~2 times greater than that of prototype compound 1. The preliminary SARs are summarized and should be helpful for future inhibitor design, and the novel scaffold presented here, with its potent inhibitory activity against FP-2, also has potential application in discovery of new anti-malarial drugs.

  恶性疟原虫 (Plasmodium falciparum) 半胱氨酸蛋白酶 (falcipain-2， FP-2) 是原生质型疟原虫的主要半胱氨酸蛋白酶和必须的血红蛋白酶，这使得它成为研制抗疟药物的一个有吸引力的靶标酶。在本研究中，我们基于用酶抑制法结合基于结构的虚拟筛选得到的化合物 1，设计并合成了系列新型小分子 FP-2 抑制剂。所有化合物均为 FP-2的高效抑制剂，其半抑制浓度 (IC50) 值范围为 1.46 至 11.38 μM，化合物 2a 的抑制活性是母体化合物 1 的 2倍左右。本研究概括总结的初步构效关系将有助于未来抑制剂的设计，这里展示的新骨架以其对 FP-2的强效抑制活性，在发现新型抗疟药物方面也具有潜在的应用价值。
• A Thieno[2,3-<i>d</i>]pyrimidine Scaffold Is a Novel Negative Allosteric Modulator of the Dopamine D₂ Receptor
  作者：Tim J. Fyfe、Barbara Zarzycka、Herman D. Lim、Barrie Kellam、Shailesh N. Mistry、Vsevolod Katrich、Peter J. Scammells、J. Robert Lane、Ben Capuano

  DOI：10.1021/acs.jmedchem.7b01565

  日期：2019.1.10

  Recently, a novel negative allosteric modulator (NAM) of the D2-like dopamine receptors 1 was identified through virtual ligand screening. This ligand comprises a thieno[2,3-d]pyrimidine scaffold that does not feature in known dopaminergic ligands. Herein, we provide pharmacological validation of an allosteric mode of action for 1, revealing that it is a NAM of dopamine efficacy and identify the structural

  最近，通过虚拟配体筛选鉴定了D 2样多巴胺受体1的新型负变构调节剂（NAM）。该配体包含在已知的多巴胺能配体中不具有的噻吩并[2,3- d ]嘧啶骨架。在此，我们提供了针对1的变构作用模式的药理学验证，表明这是多巴胺功效的NAM，并确定了这种变构的结构决定因素。我们发现关键的结构部分对于功能亲和力和负的协同作用很重要，而硫代嘧啶在5和6位的功能化导致类似物具有不同的协同作用谱。连续的化合物迭代产生了在功能亲和力方面表现出10倍改善的类似物，以及与多巴胺亲和力和功效增强的负协同性。此外，我们的研究揭示了一个片段样的核心，该核心保持了较低的μM亲和力和强大的负协同作用，并显着提高了配体效率。
• AlCl3-induced (hetero)arylation of thienopyrimidine ring: a new synthesis of 4-substituted thieno[2,3-d]pyrimidines
  作者：K. Shiva Kumar、Srinivas Chamakuri、Peddy Vishweshwar、Javed Iqbal、Manojit Pal

  DOI：10.1016/j.tetlet.2010.04.057

  日期：2010.6

  AlCl3 facilitated C–C bond forming reaction between 4-chloro-thieno[2,3-d]pyrimidines and (hetero)arenes affording a direct and single-step method for the synthesis of 4-(hetero)aryl substituted thieno[2,3-d]pyrimidines. A number of novel thienopyrimidines were prepared in good to excellent yields using this methodology. The molecular structure of a representative compound was established unambiguously

  AlCl 3促进4-氯-噻吩并[2,3- d ]嘧啶与（杂）芳烃之间的CC键形成反应，为合成4-（杂）芳基取代的噻吩并[2]提供了直接而又一步的方法。 ，3- d ]嘧啶。使用这种方法可以制备许多新颖的噻吩并嘧啶，收率良好。通过单晶X射线衍射明确地建立了代表性化合物的分子结构。
• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20090018114A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的大麻素受体配体，其中A、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• Convenient and Efficient Synthesis of Some Novel Fused Thieno Pyrimidines Using Gewald's Reaction
  作者：Ramakrishna V. S. Nirogi、Rama Sastri Kambhampati、Prabhakar Kothmirkar、Sobhanadri Arepalli、Narasimha Reddy G. Pamuleti、Anil K. Shinde、P. K. Dubey

  DOI：10.1080/00397911.2010.515357

  日期：2011.10

  Abstract Several functionalized thienopyrimidines were synthesized by a facile synthetic method, which includes Gewald's reaction, and were characterized by spectral and analytical data. These functionalized thienopyrimidines were converted to various new chemical entities of biological importance, such as 2-piperazinymethyl thienopyrimidines (6, 8), 4-dimethylaminoethoxy thienopyrimidines (11), and

  摘要 通过Gewald反应等简便的合成方法合成了几种功能化的噻吩并嘧啶，并通过光谱和分析数据进行了表征。这些功能化的噻吩并嘧啶被转化为各种具有生物学重要性的新化学实体，例如 2-哌嗪甲基噻吩并嘧啶 (6, 8)、4-二甲氨基乙氧基噻吩并嘧啶 (11) 和 3-二甲氨基乙基噻吩并嘧啶 (12)。筛选由此合成的所有化合物的体外生物活性。一些化合物显示出有希望的血清素 5-HT6 受体拮抗剂活性。