2-氧代戊烷-1,5-二甲酸二乙酯 | 5965-53-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 2-氧代戊烷-1,5-二甲酸二乙酯
• 中文别名: 2-氧代戊二酸-1,5-二乙酯；二乙基2-氧代戊二酸酯
• 英文名称: Diethyl 2-ketoglutarate
• 英文别名: diethyl 2-oxoglutarate；Diethyl 2-oxopentanedioate
• CAS: 5965-53-7
• 化学式: C₉H₁₄O₅
• mdl: MFCD00032382
• 分子量: 202.207
• InChiKey: NGRAIMFUWGFAEM-UHFFFAOYSA-N

物化性质

• 沸点：
  126-128°C 12mm
• 密度：
  0,98 g/cm3
• 闪点：
  >113°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2918300090
• 安全说明：
  S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  储存条件：室温下干燥密封保存。

SDS

Name:	Diethyl oxalpropionate 97% Material Safety Data Sheet
Synonym:	Diethyl 2-methyl-2'-oxosuccinat
CAS:	5965-53-7

Section 1 - Chemical Product MSDS Name:Diethyl oxalpropionate 97% Material Safety Data Sheet
Synonym:Diethyl 2-methyl-2'-oxosuccinat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5965-53-7	Diethyl oxalpropionate	97	227-750-3

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.
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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. 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. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. 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# 5965-53-7: 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 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: Liquid
Color: clear very slight yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 138 deg C @ 23.00 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0730 g/cm3
Molecular Formula: C9H14O5
Molecular Weight: 202.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Acids, bases, oxidizing agents, reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5965-53-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl oxalpropionate - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 5965-53-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5965-53-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5965-53-7 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

制备方法与用途

制备具体步骤如下：在500毫升的三口瓶中加入250毫升的乙醇，室温下依次加入43.8克（0.3摩尔，1.0当量）2-氧代戊二酸和22克Amberlyst 15（湿型，离子交换树脂）。加完后搅拌反应1小时，通过薄层色谱（TLC）跟踪监测反应至结束。将反应液经过过滤并浓缩处理后得到2-氧代戊烷-1,5-二甲酸二乙酯57.8克，收率约为95%。

反应信息

• 作为反应物：
  描述：

  2-氧代戊烷-1,5-二甲酸二乙酯 在 盐酸 作用下， 反应 2.0h， 以72%的产率得到alpha-酮戊二酸
  参考文献：
  名称：

  Cappon, J. J.; Baart, J.; Walle, G. A. M. van der, Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 158 - 166

  摘要：

  DOI：
• 作为产物：
  描述：

  alpha-酮戊二酸 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 2-氧代戊烷-1,5-二甲酸二乙酯
  参考文献：
  名称：

  7-fused 2-(piperazinoalkyl) indole derivatives, intermediates and

  摘要：

  具有抗过敏性能的药理活性化合物对应于公式I ##STR1##，该化合物可以在苯环中单取代或双取代，并描述了它们的酸盐和/或含有硫的化合物的S-单取代物或二氧化物，以及用于它们制备的过程和中间体。

  公开号：

  US05324725A1

文献信息

• Oxidation of hydrazones by hypervalent organoiodine reagents: Regeneration of the carbonyl group and facile syntheses of α-acetoxy and α-alkoxy azo compounds
  作者：Derek H.R. Barton、Joseph Cs. Jaszberenyi、Wansheng Liu、Tetsuro Shinada

  DOI：10.1016/0040-4020(96)00940-4

  日期：1996.11

  derivatives of α-keto esters were prepared. The carbonyl group was readily regenerated in high yield from phenylhydrazones through oxidative hydrolysis using hypervalent organoiodine(III) reagents—either bis(trifluoroacetoxy)-iodobenzene (BTIB) in aqueous acetonitrile or hydroxy(tosyloxy)iodobenzene (HTIB) in chloroform. α-Acetoxy phenyl- or methylazo compounds were readily synthesized by oxidation of the

  制备了各种α-酮酯的衍生物。使用高价有机碘（III）试剂-乙腈水溶液中的双（三氟乙酰氧基）-碘苯（BTIB）或氯仿中的羟基（甲苯磺酰氧基）碘苯（HTIB），可以通过氧化水解从苯hydr中高产率地再生羰基。通过用二氯甲烷或乙酸中的碘代苯二乙酸酯（IBDA）氧化相应的hydr，可以轻松合成α-乙酰氧基苯基或甲基偶氮化合物。α-甲氧基苯基或甲基偶氮化合物也可以通过在甲醇中氧化hydr来制备。讨论了氧化反应的机理。
• Radical Alkylations of Alkyl Halides and Unactivated C-H Bonds Using Vinyl Triflates
  作者：Sunggak Kim、Jin Lee、Kyoung-Chan Lim、Xiangjian Meng

  DOI：10.1055/s-0029-1219960

  日期：2010.7

  Radical alkylations of activated alkyl iodides and bromides were achieved using vinyl triflates in the presence of hexadimethyltin, whereas those of unactivated C-H bonds using vinyl triflates proceeded cleanly under tin-free conditions.

  在六二甲基锡的存在下，使用乙烯基三氟甲磺酸酯实现了活化的烷基碘和溴化物的自由基烷基化，而使用乙烯基三氟甲磺酸酯的未活化 CH 键的那些在无锡条件下干净地进行。
• [EN] PRODRUGS OF ALPHA-KETOGLUTARATE, ALPHA-KETOBUTYRATE, ALPHA-KETOISOVALERATE, AND ALPHA-KETOISOHEXANOATE, AND USES THEREOF<br/>[FR] PROMÉDICAMENTS D'ALPHA-CÉTOGLUTARATE, D'ALPHA-CÉTOBUTYRATE, D'ALPHA-CÉTOISOVALÉRATE, ET D'ALPHA-CÉTOISOHEXANOATE, ET LEURS UTILISATIONS
  申请人：UNIV CALIFORNIA

  公开号：WO2020081836A1

  公开（公告）日：2020-04-23

  The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

  本公开提供了能够延长寿命的化合物和组合物，以及它们的使用方法。
• Identification and Structure–Activity Relationship of HDAC6 Zinc-Finger Ubiquitin Binding Domain Inhibitors
  作者：Renato Ferreira de Freitas、Rachel J. Harding、Ivan Franzoni、Mani Ravichandran、Mandeep K. Mann、Hui Ouyang、Mark Lautens、Vijayaratnam Santhakumar、Cheryl H. Arrowsmith、Matthieu Schapira

  DOI：10.1021/acs.jmedchem.8b00258

  日期：2018.5.24

  combination therapy with proteasome inhibitors in multiple myeloma. Pharmacologically displacing ubiquitin from the zinc-finger ubiquitin-binding domain (ZnF-UBD) of HDAC6 is an underexplored alternative to catalytic inhibition. Here, we present the discovery of an HDAC6 ZnF-UBD-focused chemical series and its progression from virtual screening hits to low micromolar inhibitors. A carboxylate mimicking the

  HDAC6在募集溶酶体降解的蛋白质聚集体中起着核心作用，并且是与蛋白酶体抑制剂联合治疗多发性骨髓瘤的有希望的靶标。从HDAC6的锌指遍在蛋白结合结构域（ZnF-UBD）药理学上取代遍在蛋白是催化抑制作用的未开发的替代方法。在这里，我们介绍了以HDAC6 ZnF-UBD为重点的化学系列的发现及其从虚拟筛选命中到低微摩尔抑制剂的发展。模仿泛素的C末端末端的羧酸盐以及与W1182和R1155堆叠在一起的扩展的芳香族系统对于活性是必需的。其中一种化合物诱导了结合位点的构象重塑，其中主要的结合口袋向可配体的次要口袋开放，可用于提高效力。
• Simultaneous monitoring of the bioconversion from lysine to glutaric acid by ethyl chloroformate derivatization and gas chromatography-mass spectrometry
  作者：Yeong-Hoon Han、Tae-Rim Choi、Ye-Lim Park、Hun-Suk Song、Yong-Keun Choi、Hyun-Joong Kim、Shashi Kant Bhatia、Ranjit Gurav、Kyungmoon Park、See-Hyoung Park、Wooseong Kim、Yung-Hun Yang

  DOI：10.1016/j.ab.2020.113688

  日期：2020.5

  a gas chromatography - mass spectrometry (GC-MS) method with ethyl chloroformate (ECF) derivatization to simultaneously monitor the major metabolites. We determined the suitability of GC-MS analysis using defined concentrations of six metabolites (l-lysine, cadaverine, 5-aminovaleric acid, 2-oxoglutaric acid, glutamate, and glutaric acid) and their mass chromatograms, regression equations, regression

  戊二酸是增塑剂的前体，可用于生产聚酯酰胺，酯增塑剂，缓蚀剂等。戊二酸可以通过生物转化或化学合成产生，并且在反应过程中产生一些代谢产物和中间体。为确保反应效率，底物，中间体和产物，尤其是生物转化系统中的底物，中间体和产物，应受到密切监控。迄今为止，尽管高效液相色谱（HPLC）需要单独进行耗时的衍生化和非衍生化分析，但通常已用于分析戊二酸相关的代谢产物。为了代替这种不合理的分析方法，我们在本文中采用了氯甲酸乙酯（ECF）衍生化的气相色谱-质谱（GC-MS）方法来同时监测主要代谢物。我们使用六种代谢物（1-赖氨酸，尸胺，5-氨基戊酸，2-氧戊二酸，谷氨酸和戊二酸）的规定浓度及其质谱图，回归方程式，回归系数值（ R2），动态范围（mM）和保留时间（RT）。该方法成功地监测了复杂发酵液的生产过程。回归方程式，回归系数值（R2），动态范围（mM）和保留时间（RT）。该方法成功地监测了复杂发酵液的生产过

表征谱图