4-(4-氯苯胺)-4-氧代-2-丁酸 | 306935-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-氯苯胺)-4-氧代-2-丁酸
• 英文名称: 4'-Chloromaleanilinsaeure
• 英文别名: 3-[(4-chlorophenylamido)]propenoic acid；3-[(4-Chlorophenyl)carbamoyl]prop-2-enoic acid；4-(4-chloroanilino)-4-oxobut-2-enoic acid
• CAS: 306935-74-0
• 化学式: C₁₀H₈ClNO₃
• mdl: MFCD00185899
• 分子量: 225.631
• InChiKey: FBTQVXSNFILAQY-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  466.2±45.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• 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-(4-Chloroanilino)-4-oxobut-2-enoic acid 97% Material Safety Data Sheet
Synonym:	N-(4-Chlorophenyl)maleamic aci
CAS:	306935-74-0

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

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
306935-74-0	4-(4-Chloroanilino)-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.

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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:
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# 306935-74-0: 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: 200 - 203 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: C10H8ClNO3
Molecular Weight: 226

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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:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide, ammonia.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 306935-74-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(4-Chloroanilino)-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.

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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# 306935-74-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 306935-74-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 306935-74-0 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-(4-氯苯胺)-4-氧代-2-丁酸 在 sodium acetate 、 乙酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (3aSR,9bRS)-2-(4-chlorophenyl)-5-methyl-3a,4,5,9b-tetrahydro-1H-pyrrolo-[3,4-c]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  可见光介导的氧化镍（II）表面改性二氧化钛催化剂与马来酰亚胺的叔苯胺环化反应

  摘要：

  与未改性的TiO 2相比，由高度分散的NiO颗粒进行的表面改性的二氧化钛在可见光区域具有扩展的吸收能力，并且空穴-电子对的重组减少。它们现已成功地用作高活性多相光催化剂，在可见光介导的叔苯胺与马来酰亚胺的直接环化中，在环境温度下以中等至高收率得到四氢喹啉产品。与通常以化学计量的量与UVA光结合使用的未改性的二氧化钛催化剂相反，仅催化量（1mol％）的表面改性的TiO 2需要催化剂以及可见光以有效地催化反应。与诸如Ru（bpy）3 Cl 2或Ir（ppy）2（dtbbpy）PF 6的过渡金属配合物相比，这些表面改性的二氧化钛作为光催化剂的优点包括高催化活性，低成本，易于回收和回收。能够被使用至少九次而不会明显降低催化活性。

  DOI：

  10.1021/jo502901h
• 作为产物：
  描述：

  马来酸酐 、 对氯苯胺 以 乙醚 为溶剂， 反应 1.0h， 生成 4-(4-氯苯胺)-4-氧代-2-丁酸
  参考文献：
  名称：

  可见光介导的氧化镍（II）表面改性二氧化钛催化剂与马来酰亚胺的叔苯胺环化反应

  摘要：

  与未改性的TiO 2相比，由高度分散的NiO颗粒进行的表面改性的二氧化钛在可见光区域具有扩展的吸收能力，并且空穴-电子对的重组减少。它们现已成功地用作高活性多相光催化剂，在可见光介导的叔苯胺与马来酰亚胺的直接环化中，在环境温度下以中等至高收率得到四氢喹啉产品。与通常以化学计量的量与UVA光结合使用的未改性的二氧化钛催化剂相反，仅催化量（1mol％）的表面改性的TiO 2需要催化剂以及可见光以有效地催化反应。与诸如Ru（bpy）3 Cl 2或Ir（ppy）2（dtbbpy）PF 6的过渡金属配合物相比，这些表面改性的二氧化钛作为光催化剂的优点包括高催化活性，低成本，易于回收和回收。能够被使用至少九次而不会明显降低催化活性。

  DOI：

  10.1021/jo502901h

文献信息

• Identification of two arylimides as cholinesterase inhibitors and testing of propranolol addition on impaired rat memory
  作者：Fabiola J. Ciprés‐Flores、Eunice D. Farfán‐García、Erik Andrade‐Jorge、Roberto I. Cuevas‐Hernández、Feliciano Tamay‐Cach、Marlet Martínez‐Archundia、José G. Trujillo‐Ferrara、Marvin A. Soriano‐Ursúa

  DOI：10.1002/ddr.21633

  日期：2020.4

  (AD) is clearly linked to the decline of acetylcholine (ACh) effects in the brain. These effects are regulated by the hydrolytic action of acetylcholinesterase (AChE). Therefore, a central palliative treatment of AD is the administration of AChE inhibitors although additional mechanisms are currently described and tested for generating advantageous therapeutic strategies. In this work, we tested new arylamides

  阿尔茨海默氏病（AD）显然与大脑中乙酰胆碱（ACh）效应的下降有关。这些作用受乙酰胆碱酯酶（AChE）水解作用的调节。因此，AD的主要姑息治疗是AChE抑制剂的给药，尽管目前已描述并测试了其他机制以产生有利的治疗策略。在这项工作中，我们使用计算机软件测试了新的芳基酰胺和芳基酰亚胺作为AChE的潜在抑制剂。然后，对这些化合物进行了体外测试，两种选定的化合物C7和C8以及普萘洛尔均显示出对AChE的抑制作用。此外，与作为参考AChE抑制剂的加兰他敏相比，它们表现出有利的急性毒性。在认知障碍的动物模型中，分别使用这些化合物和普萘洛尔以及与普萘洛尔组合的每种化合物对记忆力增强进行了体内评估。在每种情况下均观察到记忆力的改善，但组合没有明显的累加作用。
• Solvent-mediated One-pot Synthesis of Cyclic<i>N</i>-Substituted Imides
  作者：Sambhaji V. Patil、Keshao A. Mahale、Kirankumar S. Gosavi、Ganesh B. Deshmukh、Nilesh S. Patil

  DOI：10.1080/00304948.2013.798569

  日期：2013.7.4

  synthesized by elaboration of N-aryl maleimides.16–19 Evaluation of the available methods for the synthesis of N-substituted cyclic imides indicates that generally the amines are first reacted with the desired cyclic anhydride and the resulting amic acids are then cyclized to the corresponding imides using reagents such as Ac2O/NaOAc, Et3N/Ac2O, dimethyl sulfate/Na2CO3/tetrabutylammonium bromide,27 cyanuric

  从现成的试剂中开发通用、高效的有机化合物合成方法是有机合成中的挑战之一。N-取代的环状酰亚胺在生物学、1-6 药理学、7 合成化学、8-19 聚合物化学、20,21 和材料科学中有许多应用。22,23 几种除草剂、24 杀虫剂、24 和抗真菌剂 1 以及宿主还通过精心设计 N-芳基马来酰亚胺合成了许多具有生物活性的天然产物。 16-19 对合成 N-取代环状酰亚胺的可用方法的评估表明，通常胺类首先与所需的环状酸酐反应，然后生成酰胺然后使用诸如 Ac2O/NaOAc、Et3N/Ac2O、硫酸二甲酯/Na2CO3/四丁基溴化铵等试剂将酸环化为相应的酰亚胺，27 氰尿酰氯/Et3N、[Bmim] [PF6]、140°C29 等。30-35 然而，其中一些程序 i) 缺乏通用性和可扩展性，ii) 使用苛刻的反应条件和危险的非绿色试剂， iii) 涉及繁琐的后处理和昂贵的试剂，iv) 产率低，有时会导致
• The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation
  作者：Guowei Xu、Yaqing Yang、Yanming Yang、Gao Song、Shanshan Li、Jiajun Zhang、Weimin Yang、Liang-Liang Wang、Zhiying Weng、Zhili Zuo

  DOI：10.1016/j.ejmech.2020.112115

  日期：2020.4

  target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells

  腺苷酸环化酶（AC）在三磷酸腺苷（ATP）转化为第二信使环单磷酸腺苷（cAMP）的过程中起关键作用。研究表明2型腺苷酸环化酶（AC2）是许多疾病的潜在药物靶标，但是，到目前为止，尚无AC2选择性激动剂的报道。在这项研究中，已经进行了基于对接的虚拟筛选与基于细胞的生物学检测相结合，以发现新型有效的和选择性的AC2激动剂。虚拟筛选揭示了一种新型的命中化合物8，作为AC2激动剂，在重组人hAC2 + HEK293细胞上的EC50值为8.10μM。在重组AC2细胞上进一步研究了基于化合物8衍生物的SAR（结构活性关系），发现化合物73是最具活性的激动剂，EC50为90 nM，它比报道的激动剂福斯高林强160倍，并且可以选择性激活AC2以抑制白介素6的表达。新型AC2选择性激动剂的发现将为研究AC2的生理功能提供一种新颖的化学探针。
• Dicarboxamide derivatives
  申请人：Boehringer Markus

  公开号：US20060106016A1

  公开（公告）日：2006-05-18

  The invention is concerned with novel dicarboxamide derivatives of formula (I) wherein A, B, R c , D and E are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit the coagulation factor Xa and can be used as medicaments.

  这项发明涉及式(I)的新颖二羧酰胺衍生物，其中A、B、Rc、D和E如描述和索赔中所定义，并且其生理上可接受的盐。这些化合物抑制凝血因子Xa，可用作药物。
• Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents
  作者：Baihui Li、Yangli Shen、Hu Wu、Xiaobo Wu、Lvjiang Yuan、Qinggang Ji

  DOI：10.1016/j.ejmech.2020.112278

  日期：2020.6

  A series of 3,4-dihydro-2(1H)-quinolinone derivatives contained butenediamide fragment were designed and synthesized. Their inhibition potency against chitin synthase and antimicrobial activities were screened in vitro. The enzymatic assays showed that all the synthesized compounds had inhibition potency against chitin synthase at concentration of 300 μg/mL. Compound 2d displayed excellent potency

  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