4-(1-萘氨基)-4-氧代-2-丁酸 | 306935-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-(1-萘氨基)-4-氧代-2-丁酸
• 中文别名: (Z)-4-(萘-1-基氨基)-4-氧代-丁-2-烯酸；(Z)-4-氧代-4-(1-萘基氨基)丁-2-烯酸；(Z)-4-(1-萘基氨基)-4-氧代-丁-2-烯酸；(2Z)-4-(1-萘基氨基)-4-氧代丁-2-烯酸
• 英文名称: 4-(1-naphthylamino)-4-oxobut-2-enoic acid
• 英文别名: NAOBEA；4-(Naphthalen-1-ylamino)-4-oxobut-2-enoic acid
• CAS: 306935-75-1
• 化学式: C₁₄H₁₁NO₃
• mdl: MFCD00021446
• 分子量: 241.246
• InChiKey: DNIIAZFRGKFYSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C
• 沸点：
  533.9±42.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2924299090

SDS

Name:	4-(1-Naphthylamino)-4-oxobut-2-enoic acid 97% Material Safety Data Sheet
Synonym:	N-(1-Naphthyl)maleamic aci
CAS:	306935-75-1

Section 1 - Chemical Product MSDS Name:4-(1-Naphthylamino)-4-oxobut-2-enoic acid 97% Material Safety Data Sheet
Synonym:N-(1-Naphthyl)maleamic aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
306935-75-1	4-(1-Naphthylamino)-4-oxobut-2-enoic a	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.

---

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# 306935-75-1: 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: 150 - 153 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: C14H11NO3
Molecular Weight: 241

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 306935-75-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(1-Naphthylamino)-4-oxobut-2-enoic acid - 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.

---

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# 306935-75-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 306935-75-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 306935-75-1 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：

  4-(1-萘氨基)-4-氧代-2-丁酸 在 sodium acetate 、 乙酸酐 作用下， 生成 1-(1-萘基)-1H-吡咯-2,5-二酮
  参考文献：
  名称：

  氧化石墨烯在水介质中作为Diels-Alder反应的碳催化剂

  摘要：

  Diels–Alder（DA）反应是[4 + 2]环加成反应，在合成有机化学中非常重要，经常用于合成包含六元环的天然产物。在本文中，我们报告了在室温下使用二维氧化石墨烯（GO）作为非均相碳催化剂在9-羟甲基蒽和N-取代的马来酰亚胺之间进行DA反应的有效方案。高收率，广泛的底物范围，低温，出色的官能团耐受性，原子经济性以及水作为绿色溶剂是该协议的重要功能。该多相GO催化剂可以容易地回收并多次使用，而催化活性没有任何明显的损失。

  DOI：

  10.1002/asia.201701072
• 作为产物：
  描述：

  马来酸酐 、 1-萘胺 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-(1-萘氨基)-4-氧代-2-丁酸
  参考文献：
  名称：

  设计，合成和生物学评估新型3,4-二氢-2（1H）-喹啉酮衍生物作为潜在的几丁质合酶抑制剂和抗真菌剂。

  摘要：

  设计合成了一系列含有丁烯二酰胺片段的3,4-二氢-2（1H）-喹啉酮衍生物。在体外筛选了它们对几丁质合酶的抑制能力和抗菌活性。酶促测定表明，所有合成的化合物在300μg/ mL的浓度下均具有针对甲壳质合酶的抑制能力。化合物2d表现出优异的效能，抑制百分数（IP）值为82.3％，而对照多恶菌素B的IP值为87.5％。IP值高于70％的化合物2b，2e和2s显示出对几丁质合酶的良好抑制能力。此外，2b的IC50值可与多恶英B（0.09 mM）相媲美。化合物2b的Ki为0.12 mM，Lineweaver-Burk图的结果表明2b是与甲壳质合酶结合的非竞争性抑制剂。抗真菌实验表明，这些化合物对真菌菌株，特别是白色念珠菌具有优异的抗真菌活性。化合物2b，2d，2e和2l对白念珠菌的抗真菌活性与氟康唑相当，并且优于多恶灵B。同时，其他化合物对白念珠菌的抗真菌活性也更好（MIC 2μg/ mL ）比化合物2n（MIC

  DOI：

  10.1016/j.ejmech.2020.112278

文献信息

• Design, synthesis, and biological evaluation of novel spiro[pyrrolidine-2,3′-quinolin]-2′-one derivatives as potential chitin synthase inhibitors and antifungal agents
  作者：Hu Wu、Chuanbiao Du、Yajie Xu、Lige Liu、Xin Zhou、Qinggang Ji

  DOI：10.1016/j.ejmech.2022.114208

  日期：2022.4

  fumigatus and A. flavus as high as fluconazole had, respectively. The sorbitol protection assay and evaluation of antifungal activity against micafungin-resistant strain further verified that these compounds possessed antifungal activity through inhibiting the synthesis of chitin of cell wall. The evaluation of antifungal activity against others drug-resistant fungi variants showed these designed compounds

  设计合成了一系列新型螺喹啉酮衍生物，并通过光谱方法对其结构进行了确证。酶学实验表明，合成的17种化合物均对几丁质合酶具有抑制作用，其中5种化合物具有与多毒素B相当的抑制作用。酶学动力学参数表明，这些化合物是几丁质的非竞争性抑制剂。合酶。抗菌实验表明，合成的化合物在体外具有选择性和广谱的抗真菌活性，其中两种化合物对白色念珠菌的抗真菌活性强于氟康唑，另外5种化合物对白念珠菌的抗真菌活性强于氟康唑。白色念珠菌等同于氟康唑。此外，有四种或五种化合物分别具有与氟康唑一样高的对新型念珠菌、烟曲霉和黄曲霉的抗真菌活性。山梨醇保护试验和对米卡芬净耐药菌株的抗真菌活性评价进一步证实了这些化合物通过抑制细胞壁几丁质的合成而具有抗真菌活性。对其他耐药真菌变体的抗真菌活性评估表明，这些设计的化合物对这些测试变体具有显着的抗真菌活性。联合使用实验表明，合成的化合物与目前临床上使用的药物具有协同作用或相加作用。这些结
• Spiro[benzoxazine-piperidin]-one derivatives as chitin synthase inhibitors and antifungal agents: Design, synthesis and biological evaluation
  作者：Yajie Xu、Yangli Shen、Chuanbiao Du、Lige Liu、Hu Wu、Qingggang Ji

  DOI：10.1016/j.ejmech.2022.114723

  日期：2022.12

  Four series of spiro[benzoxazine-piperidin]-one derivatives were designed and synthesized. Their inhibition percentages against chitin synthase and antifungal activities were evaluated. Based on the preliminary biological assays, the series of derivatives containing α, β-unsaturated carbonyl fragment which had moderate to excellent CHS inhibitory activity and antifungal activity were further researched

  设计合成了四个系列的螺[苯并恶嗪-哌啶]-酮衍生物。评估了它们对几丁质合酶和抗真菌活性的抑制百分比。在初步生物测定的基础上，进一步研究了一系列具有中至优异CHS抑制活性和抗真菌活性的α，β-不饱和羰基片段衍生物。在这一系列化合物中，21种化合物中有8种对几丁质合酶具有良好至优异的抑制活性，在300 μg/mL浓度下抑制百分率值在60%以上。其中化合物9a、9o、9s和9t表现出优异的几丁质合酶抑制活性，IC 50值分别为 0.14 mM、0.11 mM、0.10 mM 和 0.16 mM，这与对照药物 (polyoxin B) 的值相同。山梨醇保护试验的结果和对米卡芬净抗性真菌的抗真菌活性评估进一步证明了这些合成化合物的靶点是几丁质合酶。抗真菌活性评价表明，化合物9a、9d、9h、9s、9t在体外具有广谱抗真菌活性，其抗真菌活性与氟康唑和多恶英B相当。联合使用结果表明该系列化合物与氟康唑具
• Access to 8-Azabicyclo[3,2,1]octanes via the [3 + 2] Cycloaddition of Oxidopyridinium Ions to Maleimides
  作者：Cheng Yuan、Sheng Sun、Gangqiang Wang、Shaofa Sun、Jian Wang

  DOI：10.1021/acs.joc.3c00406

  日期：2023.7.7

  Herein, we reported a unique and operationally simple method to assemble 8-azabicyclo[3,2,1]octanes by using oxidopyridinium ions and maleimides as synthons. The features of good to high yields and good functional group tolerance are achieved regularly under mild conditions. Of note, oxidopyridinium ions undergo a [3 + 2] cycloaddition on their C2 and C6 positions.

  在此，我们报道了一种独特且操作简单的方法，通过使用氧化吡啶鎓离子和马来酰亚胺作为合成子来组装8-氮杂双环[3,2,1]辛烷。在温和的条件下通常可以实现良好的高产率和良好的官能团耐受性的特征。值得注意的是，氧化吡啶鎓离子在其 C2 和 C6 位置上发生 [3 + 2] 环加成。
• Ru(III)-catalyzed oxidation of pyridoxine and albuterol in pharmaceuticals
  作者：More Ashok、Adapa V.S.S. Prasad、P. Muralidhar Reddy、Vadde Ravinder

  DOI：10.1016/j.saa.2008.07.035

  日期：2009.2

  Ru(III) complexes with coordinated amide were synthesized and characterized by elemental, IR, mass, electronic, ESR spectral analysis, magnetic and conductance measurements and octahedral structures have been proposed. These complexes were used as catalysts for the oxidation of pyridoxine and albuterol in pharmaceuticals in presence of hydrogen peroxide. The role of co-oxidant and the effect of reaction time on the yields of oxidation products which were spectrophotometrically determined by condensing them with sulfanilic acid in acid medium were investigated. Structures of the oxidation products were established with the help of IR and NMR spectral analysis. (C) 2008 Elsevier B.V. All rights reserved.
• Graphene Oxide as a Carbocatalyst for a Diels-Alder Reaction in an Aqueous Medium
  作者：Yarabhally R. Girish、Subrata Pandit、Subhendu Pandit、Mrinmoy De

  DOI：10.1002/asia.201701072

  日期：2017.9.19

  six‐membered rings. Herein, we report an efficient protocol for the DA reaction between 9‐hydroxymethylanthracene and N‐substituted maleimides using two‐dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy

  Diels–Alder（DA）反应是[4 + 2]环加成反应，在合成有机化学中非常重要，经常用于合成包含六元环的天然产物。在本文中，我们报告了在室温下使用二维氧化石墨烯（GO）作为非均相碳催化剂在9-羟甲基蒽和N-取代的马来酰亚胺之间进行DA反应的有效方案。高收率，广泛的底物范围，低温，出色的官能团耐受性，原子经济性以及水作为绿色溶剂是该协议的重要功能。该多相GO催化剂可以容易地回收并多次使用，而催化活性没有任何明显的损失。