3-氧化戊二酸二叔丁酯 | 28009-80-5

• 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: 3-氧化戊二酸二叔丁酯
• 中文别名: 二叔丁基1,3-丙酮二羧酸酯；1,3-丙酮二羧酸二叔丁酯
• 英文名称: di-tert-butyl 1,3-acetonedicarboxylate
• 英文别名: Bis(1,1-dimethylethyl) 3-oxoglutarate；ditert-butyl 3-oxopentanedioate
• CAS: 28009-80-5
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: KREDQIDLGFBDMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C (lit.)
• 溶解度：
  可溶于甲醇：1g/10mL，澄清，无色至淡黄色
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 储存条件：
  存放于2-8℃阴凉干燥处

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Di-tert-butyl 1,3-acetonedicarboxylate
CAS-No. : 28009-80-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Di-tert-butyl 3-oxoglutarate
Formula : C13H22O5
Molecular Weight : 258,31 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: crystalline
Colour: beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 58 - 60 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-氧化戊二酸二叔丁酯 以 乙腈 为溶剂， 生成 (tert-butoxy)carbonylmethyl radical
  参考文献：
  名称：

  氰基（·CH 2 CN）和（叔丁氧基）羰基甲基（·CH 2 CO 2 C（CH 3）3）自由基加成溶液中烯烃的绝对速率常数

  摘要：

  通过时间分辨电子自旋共振确定绝对速率常数及其温度依赖性，方法是将自由基·CH 2 CN和·CH 2 CO 2 C（CH 3）3添加到各种单取代和1,1-二取代基中并在乙腈溶液中选择1,2-和三取代的烯烃。·CH 2 CN在烯烃CH 2 CXY处以未取代的C原子加成，其速率常数范围为3.3·10 3 M -1 S -1（乙烯）至2.4·10 6 M -1 S -1（1，1-二苯基乙烯）在278 K，并且频率因子在log的窄范围内（A / M -1 S -1）= 8.7±0.3。·CH 2 CO 2 C（CH 3）3具有非常相似的反应性，在296 K时的速率常数为1.1·10 4 M -1 S -1（乙烯）至10 7 M -1 S -1（1,1 -二苯乙烯）和频率因子log（A / M -1 S -1）= 8.4±0.1。对于两个自由基，速率常数和添加到CH 2中的活化能CXY与总反应焓密切相

  DOI：

  10.1002/hlca.19950780118
• 作为产物：
  描述：

  丙二酸单叔丁酯 在 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以96%的产率得到3-氧化戊二酸二叔丁酯
  参考文献：
  名称：

  活化丙二酸半酯的自缩合：聚酮化合物生物合成中脱羧性克莱森缩合的模型

  摘要：

  丙二酸半含氧酸酯与N-羟基琥珀酰亚胺基酯形成试剂的反应导致自缩合，从而提供相应的1，3-丙酮二羧酸二酯。此新方法不需要二价金属螯合剂或配位溶剂即可成功缩合。

  DOI：

  10.1016/j.tetlet.2003.08.014

文献信息

• General approach for the synthesis of polyquinenes via the weiss reaction XII. The chugaev approach to ellacene (1,10-cyclododecanotriquinancene)
  作者：Xiaoyong Fu、James M. Cook

  DOI：10.1016/s0040-4039(00)97409-4

  日期：1990.1

  The synthesis of ellacene (1,10-cyclododecanotriquinancene) 2 has been achieved via the Weiss reaction. The regiospecific monoallylation of 6 to provide 7, and the pyrolysis of tris xanthate 11 in HMPA at 220°C to furnish 2 represent the key steps in the sequence. The HMPA-mediated dehydration of triol 10 to form the ethers 12 and 13 in preference to the desired 2 has also been observed.

  鞣花烯（1,10-环十二烷三喹啉）2的合成已通过Weiss反应完成。6的区域特异性单烯丙基化以提供7，以及三甲基黄酸酯11在HMPA中在220°C的高温下热解以提供2，这代表了该序列中的关键步骤。还已经观察到HMPA介导的三醇10的脱水以形成优先于所需的2的醚12和13。
• Substituted biphenyls
  申请人：Bayer Corporation

  公开号：US06218431B1

  公开（公告）日：2001-04-17

  Substituted biphenyls having glucagon receptor antagonistic activity. Claimed compounds have the formula wherein R1a and R1b independently represent (C1-C6) alkyl; R2 represents (C1-C10) alkyl or substituted (C1-C10) alkyl wherein the substituents are independently from 1 to 3 of —SR7; R7 represents phenyl, or substituted phenyl wherein the substituents are independently 1-5 of halogen, trifluoromethyl, (C1-C6) alkyl, (C1-C6) alkoxy, nitro, cyano, or hydroxyl; R3 represents substituted (C1-C6) alkyl wherein the substituents are 1-2 hydroxyl groups; G represents a substituent selected from the group consisting of halogen, (C1-C6) alkyl, and OR4 wherein R4 is H or (C1-C6) alkyl; and y is 0 or an integer of 1-3. Pharmaceutical compositions containing such compounds and methods of treatment of glucagon-mediated conditions by administering such compounds are also claimed.

  具有胰高血糖素受体拮抗活性的取代联苯。所述化合物的结构式如下：其中R1a和R1b分别代表（C1-C6）烷基；R2代表（C1-C10）烷基或取代的（C1-C10）烷基，其中取代基独立地为1至3个-SR7；R7代表苯基，或取代的苯基，其中取代基独立地为1-5个卤素、三氟甲基、（C1-C6）烷基、（C1-C6）烷氧基、硝基、氰基或羟基；R3代表取代的（C1-C6）烷基，其中取代基为1-2个羟基；G代表从卤素、（C1-C6）烷基和OR4（其中R4为H或（C1-C6）烷基）组成的取代基；y为0或1-3的整数。还声明了含有这类化合物的药物组合物以及通过给予这类化合物治疗胰高血糖素介导疾病的方法。
• 一种贝派地酸的合成方法及其中间体
  申请人：杭州科巢生物科技有限公司

  公开号：CN112110828A

  公开（公告）日：2020-12-22

  本发明公开了贝派地酸的新中间体化合物6和化合物7，同时还公开了贝派地酸的合成方法，该方法缩短了路线步骤，提供了收率，降低了工艺成本，并且改进了贝派地酸中间体的结构提高了它们的结晶性能，利于提高最终产品的纯度，适合放大生产。化合物6和化合物7的结构式如下所示：其中，‑N(R2)2表示为N,N‑二甲氨基、环己胺基、吗啉基或氨基；其中，M为无机碱或有机碱，包括钠、钾、钙、环己二胺或吗啉。
• A convenient method for the synthesis of 3,6-dihydroxy-benzene-1,2,4,5-tetracarboxylic acid tetraalkyl esters and a study of their fluorescence properties
  作者：Aswathy L. Balachandran、Vidya Sathi、Ani Deepthi、Chettiyam V. Suneesh

  DOI：10.3998/ark.5550190.p009.843

  日期：——

  A mild, efficient and simple method for the synthesis of 3,6-dihydroxy-1,2,4,5-tetracarboxylic tetraalkyl esters using cerium(IV) ammonium nitrate mediated oxidation of 1,3-acetone dicarboxylates has been developed. The detailed absorption and emission studies of the synthesized compounds reveal that these molecules have appreciable quantum yields and possess large Stokes shift values.

  已开发出一种温和、高效且简单的方法，用于使用硝酸铈 (IV) 铵介导的 1,3-丙酮二羧酸酯氧化合成 3,6-二羟基-1,2,4,5-四羧酸四烷基酯。合成化合物的详细吸收和发射研究表明，这些分子具有可观的量子产率和大斯托克斯位移值。
• A new synthetic method for allene-1,3-dicarboxylates using DMC and a novel tandem cyclization to a pyrrolizidine alkaloid skeleton
  作者：Manabu Node、Toshio Fujiwara、Shogo Ichihashi、Kiyoharu Nishide

  DOI：10.1016/s0040-4039(98)01344-6

  日期：1998.8

  one-step synthesis of allene-1,3-dicarboxylates from acetone-1,3-dicarboxylates in high yields was developed by the use of DMC as a dehydrating reagent. This process opened a new expeditious route to a 1-azabicyclo[3.3.0]octane skeleton of pyrrolizidine alkaloids from dimethyl acetone-1,3-dicarboxylate and bis(2-chloroethyl)amine via a Michael addition and a novel tandem cyclization.

  通过使用DMC作为脱水试剂，高产率地从1,3-二羧酸丙酮中合成了1,3-二羧酸Allene-1。此过程开辟了一条新的快速途径，即通过迈克尔加成反应和新颖的串联环化反应，从1,3-二羧酸二甲酯和双（2-氯乙基）胺合成吡咯烷核生物碱的1-azabicyclo [3.3.0]辛烷骨架。

表征谱图