6-氨基-5-氰基-2-甲基-4-苯基-4H-吡喃-3-羧酸乙酯 | 72568-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 6-氨基-5-氰基-2-甲基-4-苯基-4H-吡喃-3-羧酸乙酯
• 英文名称: 2-amino-3-cyano-5-ethoxycarbonyl-6-methyl-4-phenyl-4H-pyran
• 英文别名: ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate；6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylic acid ethyl ester
• CAS: 72568-47-9
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: XTMWVOYEFHWDDN-UHFFFAOYSA-N

物化性质

• 熔点：
  465-467 °C
• 沸点：
  497.2±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 溶解度：
  37.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 安全说明：
  S36/37

SDS

Name:	Ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	72568-47-9

Section 1 - Chemical Product MSDS Name:Ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
72568-47-9	Ethyl 6-amino-5-cyano-2-methyl-4-pheny	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
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:

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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# 72568-47-9: 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: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 189 - 190 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: C16H16N2O3
Molecular Weight: 284.31

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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:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 72568-47-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-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
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 72568-47-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 72568-47-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 72568-47-9 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：

  6-氨基-5-氰基-2-甲基-4-苯基-4H-吡喃-3-羧酸乙酯 在 一水合肼 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 6-amino-5-cyano-2-methyl-N'-(4-methyl-3-phenylthiazol-2(3H)-ylidene)-4-phenyl-4H-pyran-3-carbohydrazide
  参考文献：
  名称：

  Novel synthesis of pyran-3-hydrazide derivatives and their uses to the synthesis hydrazide-hydrazone, pyrazole and thiazole derivatives with anticancer activities

  摘要：

  摘要：在三乙胺存在的乙醇中，乙酰乙酸乙酯与丙二腈（3）苯甲醛（1）分别反应，得到乙酰基苯甲酸乙酯的乙酯6-氨基-5-氰基-2-甲基-4-苯基-4H-吡喃-3-羧酸酯（4）。后者化合物与水合肼反应，得到肼衍生物6。化合物6经过一系列的杂环化反应，得到吡唑，肼肟-肼酮，噻唑衍生物。所生产的化合物对六种癌细胞系进行了测试，并表明化合物8b，10b，11a，17a，21和24a是最具细胞毒性的化合物。后来对这些化合物进行了进一步测试，针对五种酪氨酸激酶和Pim-1激酶，发现化合物10b，21和24a是测试化合物中最有效的，化合物10a，11a和17a对Pim-1激酶的抑制作用最高。大多数测试化合物对选定的癌细胞系和酪氨酸激酶的高抑制作用鼓励未来进行更多的研究。 关键词：肼酰肼，噻吩，吡唑，吡喃，细胞毒性，酪氨酸激酶 《埃塞俄比亚化学学会杂志》2021年第35卷第3期，573-586页。 DOI：https://dx.doi.org/10.4314/bcse.v35i3.9

  DOI：

  10.4314/bcse.v35i3.9
• 作为产物：
  描述：

  苯甲醛 在 二甲胺 作用下， 以 乙醇 为溶剂， 反应 0.16h， 生成 6-氨基-5-氰基-2-甲基-4-苯基-4H-吡喃-3-羧酸乙酯
  参考文献：
  名称：

  吡喃环杂环支架的合成：使用二甲胺的高度方便的协议

  摘要：

  通过在二甲胺存在下通过一锅缩合芳香族醛，丙二腈和不同的可烯丙基化C-H活化酸性化合物，开发了一种可药用的吡喃环杂环的快速简便的三组分合成方法。 -乙醇在温和的反应条件下制得的催化剂。各种吡喃衍生物的选择性取决于烯醇化物的结构。本方案具有合成优势，无需色谱即可在短得多的反应时间内获得优异的收率。

  DOI：

  10.1007/s11164-014-1873-5

文献信息

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• One-pot synthesis of some 2-amino-4H-chromene derivatives using triethanolamine as a novel reusable organocatalyst under solvent-free conditions and its application in electrosynthesis of silver nanoparticles
  作者：B. Maleki、M. Baghayeri、S. Sheikh、S. Babaee、S. Farhadi

  DOI：10.1134/s1070363217050280

  日期：2017.5

  2-amino-4H-chromene derivatives. Its advantages include short reaction time, high yields, low cost, and straightforward work-up. Triethanolamine is an efficient reusable catalyst. 2-Amino-4H-benzo[g]chromenes (ABgC) were applied as novel components of electro synthesis of silver nanoparticles.

  通过芳族醛和丙二腈与2-羟基萘-1,4-二酮的一锅三组分反应，有效地制备了在4 H-色烯环上具有不同取代基的各种2-氨基-4 H-色烯衍生物在无溶剂条件下，在三乙醇胺存在下作为乙酰乙酸乙酯或萘酚作为一种新的有机催化剂。该方法是无过渡金属的且对各种2-氨基-4 H-色烯衍生物无害于环境的方法。其优点包括反应时间短，产率高，成本低和后处理简单。三乙醇胺是一种有效的可重复使用的催化剂。2-氨基-4 H-苯并[ g对苯二甲腈（ABgC）被用作银纳米粒子电合成的新型组分。
• One-pot synthesis of 2-amino-3-cyano-4<i>H</i>-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol
  作者：Aiborlang Thongni、Pynskhemborlang T. Phanrang、Arup Dutta、Rishanlang Nongkhlaw

  DOI：10.1080/00397911.2021.1998535

  日期：2022.1.2

  shorter reaction time, utilization of eco-friendly solvents, operational simplicity, mild reaction conditions, and maximum product yield. Moreover, the use of sodium citrate as an easily available, cheap and benign catalyst plays a pivotal role from a green perspective, considering its high recyclability and easy recovery. Therefore, this present methodology offers numerous possibilities in terms of large-scale

  摘要 柠檬酸钠作为一种高效催化剂被开发用于合成官能化的 2-氨基-3-氰基-4 H-吡喃和吡喃环化杂环。该方法涉及芳香醛、丙二腈和 1,3-二羰基化合物与 EtOH 的一锅三组分反应：H 2O (1:1 v/v) 在室温下作为溶剂。该协议具有几个优点，例如更短的反应时间、环保溶剂的利用、操作简单、反应条件温和和产品收率最高。此外，考虑到柠檬酸钠的高可回收性和易回收性，从绿色角度来看，柠檬酸钠作为一种易于获得、廉价和良性的催化剂发挥着关键作用。因此，本方法在大规模工业合成或应用于众多有机转化方面提供了许多可能性。此外，还对产物4aa形成的机理途径进行了理论研究，以确定柠檬酸钠对DFT法反应可行性的催化作用，使用B3LYP泛函。
• 2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate: a biodegradable and recyclable ionic liquid for the one-pot synthesis of 2-amino-3-cyano-4H-pyrans
  作者：Moones Honarmand、Andromachi Tzani、Anastasia Detsi

  DOI：10.1007/s13738-018-1537-2

  日期：2019.3

  2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate ‘HAHS’ was synthesized as a novel ionic liquid and characterized by various techniques. ‘HAHS’ ionic liquid was efficiently applied as a multifunctional promoter for the three-component synthesis of 2-amino-3-cyano-4H-pyrans. The 2-amino-3-cyano-4H-pyrans were produced not only in high to excellent yields but also no toxic solvent or catalyst was used. ‘HAHS’ ionic liquid was recovered and reused four times without the considerable decreasing in its activity. The effect of hydroxyl groups in the structure of ‘HAHS’ ionic liquid on its catalytic activity was studied. Moreover, the biodegradability potential of the ionic liquid was examined using the 5-day biological oxygen demand closed bottle test and the results showed that ‘HAHS’ has remarkable biodegradability potential.

  2-羟乙基-1-铵-3-羟基丙烷-1-磺酸盐（HAHS）作为一种新型离子液体被合成，并通过多种技术手段进行了表征。HAHS离子液体被高效应用于2-氨基-3-氰基-4H-吡喃的三组分合成中，不仅产率从高到极佳，而且无需使用有毒溶剂或催化剂。HAHS离子液体可回收并重复使用四次，活性无显著下降。研究了HAHS离子液体结构中的羟基对其催化活性的影响。此外，通过5天生物需氧量闭瓶测试考察了该离子液体的生物降解潜力，结果显示HAHS具有显著的生物降解潜力。
• Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one-pot three-component synthesis of pyran derivatives
  作者：Seyedeh Fatemeh Hojati、Amirhassan Amiri、Nasrin MoeiniEghbali、Sakineh Mohamadi

  DOI：10.1002/aoc.4235

  日期：2018.4

  Polypyrrole (PPY)/Fe3O4/CNT has been synthesized and characterized by FT‐IR, TEM and SEM techniques and its catalytic activity has been evaluated in the synthesis of several series of pyran derivatives. Tetrahydrobenzo[b]pyranes, 4H‐pyran‐3‐carboxylates, 4H,5H‐pyrano[3,2‐c]chromenes and dihydropyrano[2,3‐c]pyrazoles have been successfully prepared from one‐pot three‐component condensation of aldehyde

  聚吡咯（PPY）/ Fe 3 O 4 / CNT的合成已通过FT-IR，TEM和SEM技术进行了表征，并在几种吡喃衍生物系列的合成中对其催化活性进行了评估。四氢苯并[ b ]吡喃，4H-吡喃-3-羧酸盐，4H，5H-吡喃并[3,2- c ]苯并二氢吡喃并[2,3- c ]吡唑已成功地由一锅三组分缩合反应制得。醛，丙二腈和含活性亚甲基的化合物（二甲酮/乙酰乙酸乙酯/ 4-羟基香豆素/ 3-甲基-2-吡唑啉-5-酮），使用PPY / Fe 3 O 4/ CNT作为一种新的可重复使用的多相催化剂。本方法具有几个优点，例如：产物的高收率，较短的反应时间，容易的后处理步骤以及由于其磁性而易于从反应混合物中分离出催化剂。此外，通过这种方法可以从对苯二甲醛化学选择性合成双苯并[ b ]吡喃。