4-(4-乙氧基苯基)-2,4-二氧代丁酸甲酯 | 108783-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(4-乙氧基苯基)-2,4-二氧代丁酸甲酯
• 英文名称: 4-(4-ethoxyphenyl)-2,4-dioxo-butyric acid methyl ester
• 英文别名: Methyl 4-(4-ethoxyphenyl)-2,4-dioxobutanoate
• CAS: 108783-91-1
• 化学式: C₁₃H₁₄O₅
• mdl: MFCD05686794
• 分子量: 250.251
• InChiKey: PFPBZQIEMJJXBN-UHFFFAOYSA-N

物化性质

• 沸点：
  407.0±25.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-(4-ethoxyphenyl)-2,4-dioxobutanoate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 4-(4-ethoxyphenyl)-2,4-dioxobutanoate
CAS number: 108783-91-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H14O5
Molecular weight: 250.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(4-乙氧基苯基)-2,4-二氧代丁酸甲酯 在 三氧化二氮 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  一类1,5-二苯基吡唑-3-羧酸类化合物及其应 用

  摘要：

  本发明提供了一类1,5‑二苯基吡唑‑3‑羧酸类化合物及其应用，所述化合物具有通式I的结构，其中：R1选自‑H、卤素、C1～C6的饱和烷基或‑X1‑R4；R2选自H、卤素、C1～C6的饱和烷基或‑X2‑R5；R3选自H、‑NH2或‑NH‑CO‑Ph‑(o﹑m﹑p)R6；R6选自H、卤素、C1～C6的饱和烷基或‑O‑R7；X1和X2分别独立选自O或S；R4、R5和R7分别独立选自H、C1～C6的饱和烷基、苄基或C1～C6的饱和烷基取代的苯基。本发明的化合物同时模拟BH3‑only和p53TAD蛋白α‑螺旋，竞争性结合和拮抗Mcl‑1、Bcl‑2和MDM2蛋白，特异性引起肿瘤细胞凋亡，实现其作为抗癌化合物的应用。

  公开号：

  CN105061315B
• 作为产物：
  描述：

  草酸二甲酯 、 4-乙氧基苯乙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4-(4-乙氧基苯基)-2,4-二氧代丁酸甲酯
  参考文献：
  名称：

  探索绕丹宁连接的烯胺-碳酰肼衍生物作为分枝杆菌碳酸酐酶抑制剂：设计、合成、生物学评价和分子对接研究

  摘要：

  随着耐多药结核病的兴起，寻找一种结合新作用机制的替代性优质治疗方案变得至关重要。为了实现这一目标，我们开发并合成了一系列新的绕丹宁连接的烯胺碳酰肼衍生物，探索它们作为分枝杆菌碳酸酐酶抑制剂的潜力。研究结果揭示了它们的功效，对分枝杆菌碳酸酐酶 2 (mtCA 2) 酶表现出显着的选择性。该系列化合物虽然对人碳酸酐酶异构体表现出中等活性，但表现出良好的选择性，将这些化合物定位为潜在的抗结核药物。化合物6d是该系列中最好的一种，对 mtCA 2 的K i值为 9.5 µM。大多数化合物对 Mtb H37Rv 菌株表现出中等至良好的抑制作用；化合物11k的最低抑制浓度为 1 µg/mL。分子对接研究表明，化合物6d和11k显示出与锌离子的金属配位，就像经典的 CA 抑制剂一样。

  DOI：

  10.1002/ardp.202400064

文献信息

• Synthesis and antibacterial activity of 1-substituted 5-aryl-4-aroyl-3-hydroxy-3-pyrrolin-2-ones
  作者：V. L. Gein、S. G. Pitirimova、É. V. Voronina、N. Yu. Porseva、V. I. Pantsurkin

  DOI：10.1007/bf02464279

  日期：1997.11

  5-aryl-3-hydroxy-3-pyrrolin-2-ones exhibit various types of pharmacological activity, depending on the character of substituents in positions 1 and 4. For example, the introduction of an alkoxycarbonyl group in position 4 and an aromatic substituent in position 1 leads to compounds possessing pronounced antiviral activity [1], while the presence of a carboxymethyl group in position 4 imparts antiinflammatory

  以前我们已经证明 1,4-二取代的 5-芳基-3-羟基-3-吡咯啉-2-ones 表现出各种类型的药理活性，这取决于位置 1 和 4 上取代基的特征。例如，引入4 位的烷氧基羰基和 1 位的芳族取代基导致化合物具有显着的抗病毒活性 [1]，而 4 位的羧甲基赋予该物质抗炎特性 [2]。在我们继续研究结构因素对 1,4,5-三取代 3-吡咯啉-2-ones 药理活性的影响时，引入二乙氨基乙基药效基团是有意义的，使产品~，水溶性，在吡咯环的位置 1。这可能有助于我们确定分子的亲水特性对其药理活性的影响。为此，我们通过等摩尔量的 4-芳基-2 酯之间的反应合成了一系列 5-芳基-4-芳酰基-(2-二乙氨基乙基)-3-羟基-3-吡咯啉-2-酮 (I XI)， 4-二氧代丁酸、取代的苯甲醛和 2-(N,N-二乙氨基)乙胺的乙醇溶液，室温。
• Methyl 3-aroyl-4-oxo-1,4-dihydroquinoline-2-carboxylates: synthesis and molecular and crystal structures
  作者：A. A. Boteva、O. P. Krasnykh、I. V. Fefilova、E. B. Babushkina、P. A. Slepukhin

  DOI：10.1007/s11172-014-0499-5

  日期：2014.3

  decarbonylation of methyl 1-aryl-3-(het)aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates afforded 8-substituted methyl 3-(het)aroyl-4-oxo-1,4-dihydroquinoline-2-carboxylates. X-ray diffraction studies revealed no hydrogen bonds in the crystals of the compounds obtained. According to spectral data, hydrogen bonding is possible in concentrated solutions of 8-substituted methyl 4-oxo-1,4-dihydroq

  1-芳基-3-(het)aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates 甲基的热脱羰得到 8-取代的甲基 3-(het)aroyl-4-oxo- 1,4-二氢喹啉-2-羧酸盐。X 射线衍射研究表明在所得化合物的晶体中没有氢键。根据光谱数据，在 8-取代的 4-氧代-1,4-二氢喹啉-2-羧酸甲酯的浓溶液中可能存在氢键。
• Five-Membered 2,3-Dioxo Heterocycles: L. Synthesis and Thermolysis of 3-Aroyl- and 3-Hetaroyl-5-phenyl-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxalin-1,2,4-triones
  作者：K. S. Bozdyreva、I. V. Smirnova、A. N. Maslivets

  DOI：10.1007/s11178-005-0296-6

  日期：2005.7

  (Z)-3-Phenacylidene- and (Z)-3-hetaroylmethylidene-1-phenyl-1,2,3,4-tetrahydroquinoxalin-2-ones react with oxalyl chloride to give 3-acyl-5-phenyl-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-1,2,4-triones. Thermolysis of the latter generates acyl(3-oxo-4-phenyl-3,4-dihydroquinoxalin-2-yl)ketenes which are stabilized via [4 + 2]-cyclodimerization followed by [1,3]-acylotropic shift to afford 4-acyl-3-acyloxy-2-(3-oxo-4-phenyl-3,4-dihydroquinoxalin-2-yl)-6-phenyl-5,6-dihydro-1H-pyrido[1,2-a]quinoxaline-1,5-diones.

  (Z)-3-苯乙烯基和(Z)-3-杂芳基甲烯基-1-苯基-1,2,3,4-四氢喹喔啉-2-酮与草酰氯反应产生3-酰基-5-苯基-1,2,4,5-四氢吡咯[1,2-a]喹喔啉-1,2,4-三酮。后者的热解产生酰基(3-氧基-4-苯基-3,4-二氢喹喔啉-2-基)酮烯，这些产物通过[4 + 2]环二聚反应稳定，随后发生[1,3]酰基迁移，得到4-酰基-3-酰氧基-2-(3-氧基-4-苯基-3,4-二氢喹喔啉-2-基)-6-苯基-5,6-二氢-1H-吡啶[1,2-a]喹喔啉-1,5-二酮。
• Bcl-2/MDM2 Dual Inhibitors Based on Universal Pyramid-Like α-Helical Mimetics
  作者：Ziqian Wang、Ting Song、Yingang Feng、Zongwei Guo、Yudan Fan、Wenjie Xu、Lu Liu、Anhui Wang、Zhichao Zhang

  DOI：10.1021/acs.jmedchem.5b01913

  日期：2016.4.14

  No alpha-helical mimetic that exhibits Bd-2/MDM2 dual inhibition has been rationally designed due to the different helicities of the alpha-helixes at their binding interfaces. Herein, we extracted a one-turn alpha-helix-mimicking ortho-triarene unit from o-phenylene foldamers. Linking benzamide substrates with a rotatable C-N bond, we constructed a novel semirigid pyramid-like scaffold that could support its two-turn alpha-helix mimicry without aromatic stacking interactions and could adopt the different dihedral angles of the key residues of p53 and BH3-only peptides. On the basis of this universal scaffold, a series of substituent groups were installed to capture the key residues of both p53TAD and BimBH3 and balance the differences of the bulks between them. Identified by FP, ITC, and NMR spectroscopy, a compound 6e (zq-1) that directly binds to Mcl-1, Bcl-2, and MDM2 with balanced submicromolar affinities was obtained. Cell-based experiments demonstrated its antitumor ability through Bcl-2/MDM2 dual inhibition simultaneously.
• Andreichikov, Yu. S.; Gein, V. L.; Anikina, I. N., Journal of Organic Chemistry USSR (English Translation), 1986, p. 1572 - 1577
  作者：Andreichikov, Yu. S.、Gein, V. L.、Anikina, I. N.

  DOI：——

  日期：——