(S)-(-)-2-氧代-1,5-咪唑烷二羧酸 1-苄酯 | 59760-01-9

• 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: (S)-(-)-2-氧代-1,5-咪唑烷二羧酸 1-苄酯
• 中文别名: (S)-(-)-2-氧代-1,5-咪唑烷二羧酸1-苄酯；(S)-(-)-1-Z-2-氧-5-咪唑烷羧酸；(S)-(-)-2-氧代-1,5-咪唑啉二羧酸-1-苄酯
• 英文名称: (S)-2-oxo-imidazolidine-1,5-dicarboxylic acid 1-benzyl ester
• 英文别名: (S)-3-((benzyloxy)carbonyl)-2-oxoimidazolidine-4-carboxylic acid；(4S)-3-(benzyloxycarbonyl)-2-oxoimidazolidine-4-carboxylic acid；3-benzyloxycarbonyl-2-oxoimidazolidine-4(S)-carboxylic acid；(S)-(-)-1-Z-2-oxo-5-imidazolidinecarboxylic acid；(4S)-2-oxo-3-phenylmethoxycarbonylimidazolidine-4-carboxylic acid
• CAS: 59760-01-9
• 化学式: C₁₂H₁₂N₂O₅
• 分子量: 264.238
• InChiKey: AYSUEIZKNBGWGN-VIFPVBQESA-N

物化性质

• 熔点：
  189 °C (dec.)(lit.)
• 密度：
  1.444±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。应储存在阴凉、干燥的地方。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: (S)-(−)-1-Z-2-Oxo-5-imidazolidinecarboxylic acid
Product name
CAS-No. : 59760-01-9
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
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: (S)-(−)-2-Oxo-1,5-imidazolidinedicarboxylic acid 1-benzyl ester
Synonyms
Formula : C12H12N2O5
Molecular Weight : 264,23 g/mol
Component Concentration
(S)-(-)-2-Oxo-1,5-imidazolidinedicarboxylic acid 1-benzyl ester
CAS-No. 59760-01-9 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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, nitrogen oxides (NOx)
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. 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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
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 use(s)
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
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 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
Impervious clothing., The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 189 °C - dec.
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) Auto-ignition 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 agentsStrong 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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
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

制备方法与用途

用途：Z-保护咪唑烷酮用于连续N-烷基化反应。

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-氧代-1,5-咪唑烷二羧酸 1-苄酯 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 138.0h， 生成 (1'S,2'R,5'S)-menthyl 1-acetyl-3-benzyloxycarbonyl-2-oxoimidazolidine-4(S)-carboxylate
  参考文献：
  名称：

  Stereoselectivity in metal carbene and Lewis acid-catalyzed reactions from diastereomeric dirhodium(II) carboxamidates: Menthyl N-acetyl-2-oxoimidazolidine-4(S)-carboxylates

  摘要：

  The influence of a chiral menthyl group as the pendant ester substituent on the N-acetyl-2-oxoimidazolidine-4S-carboxylate ligands in chiral dirhodium(II) imidazolidinone catalysts has been examined. Significant match/mismatch influences are evident in the observed stereocontrol for carbon-hydrogen insertion reactions with diazoacetates, but these effects are minimal in cyclopropanation reactions. Steric restrictions prevent effective enantiocontrol in hetero-Diels-Alder reactions using these menthyl-substituted catalysts. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.05.032
• 作为产物：
  描述：

  N-苄氧羰基-L-天冬酰胺 在 次溴酸 作用下， 以83%的产率得到(S)-(-)-2-氧代-1,5-咪唑烷二羧酸 1-苄酯
  参考文献：
  名称：

  烯丙基三烷基硅烷的非对映选择性[3 + 2]环加成到由4-甲氧基-2-咪唑啉酮-甲基和2-恶唑烷酮-4-羧酸甲酯制得的中间体N-丙氨酸酯

  摘要：

  甲基-4-甲氧基-2-咪唑啉酮-4-羧酸酯或甲基用烯丙基硅烷如的TiCl的存在的亲核试剂4-甲氧基-2-恶唑烷酮-4-羧酸盐的amidoalkylation反应4只得到三个碳环环产品5和9经由[3 + 2]环加成。除此之外，形成简单的甲氧基取代产物。环环化实际上以总的非对映选择性发生，因此所有取代基均位于双环产物的β侧。

  DOI：

  10.1016/0040-4039(94)85317-7

文献信息

• THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE
  申请人：Lemieux Rene M.

  公开号：US20150031627A1

  公开（公告）日：2015-01-29

  Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

  提供的方法是治疗一种由IDH1/2突变等位基因特征性存在的癌症，包括向需要此治疗的患者施用此处描述的化合物。
• [EN] THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE<br/>[FR] COMPOSÉS THÉRAPEUTIQUEMENT ACTIFS ET LEURS MÉTHODES D'UTILISATION
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2015010297A1

  公开（公告）日：2015-01-29

  Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

  提供的方法是治疗一种由IDH1/2突变等位基因特征性存在的癌症，包括向需要此治疗的患者施用此处描述的化合物。
• Studies on angiotensin converting enzyme inhibitors. 4. Synthesis and angiotensin converting enzyme inhibitory activities of 3-acyl-1-alkyl-2-oxoimidazolidine-4-carboxylic acid derivatives
  作者：Kimiaki Hayashi、Kenichi Nunami、Jyoji Kato、Naoto Yoneda、Masami Kubo、Takashi Ochiai、Ryuichi Ishida

  DOI：10.1021/jm00122a003

  日期：1989.2

  (4S)-1-Alkyl-3-[[N-(carboxyalkyl)amino]acyl]-2-oxoimidazolidine-4- carboxylic acid derivatives (3) were prepared by two methods. Their angiotensin converting enzyme (ACE) inhibitory activities and antihypertensive effects were evaluated, and the structure-activity relationships were discussed. The dicarboxylic acids 3a-n possessing S,S,S configuration showed potent in vitro ACE inhibitory activities

  通过两种方法制备（4S）-1-烷基-3-[[[N-（羧烷基）氨基]酰基] -2-氧代咪唑烷-4-羧酸衍生物（3）。评估了它们对血管紧张素转化酶（ACE）的抑制活性和降压作用，并讨论了它们之间的构效关系。具有S，S，S构型的二元羧酸3a-n显示出有效的体外ACE抑制活性，IC50值为1.1 X 10（-8）-1.5 X 10（-9）M.在该系列中最有效的化合物是单酯3p，ID50值为0.24 mg / kg，在正常血压大鼠中抑制血管紧张素I诱导的升压反应，在剂量为1-10 mg / kg时自发性高血压大鼠（SHRs）的收缩压呈剂量依赖性降低。公斤，磅
• [EN] CYCLIC UREA COMPOUNDS AS GRANZYME B INHIBITORS<br/>[FR] COMPOSÉS D'URÉE CYCLIQUE EN TANT QU'INHIBITEURS DU GRANZYME B
  申请人：VIDA THERAPEUTICS INC

  公开号：WO2016015160A1

  公开（公告）日：2016-02-04

  Cyclic urea compounds as Granzyme B inhibitors, compositions that include the compounds, and methods for using the compounds. Methods for treating cutaneous scleroderma, epidermolysis bullosa, radiation dermatitis, alopecia areata, and discoid lupus erythematosus are provided.

  环脲化合物作为Granzyme B抑制剂，包括该化合物的组合物，以及使用该化合物的方法。提供了治疗皮肤硬化症、表皮溃疡、放射性皮炎、斑秃和盘状红斑狼疮的方法。
• Bicyclic-Fused Heteroaryl or Aryl Compounds
  申请人：Pfizer Inc.

  公开号：US20150284405A1

  公开（公告）日：2015-10-08

  Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  所述化合物的异构体和药学上可接受的盐已被披露，其中所述化合物具有如规范中定义的Ia式结构。相应的药物组合物、治疗方法、合成方法和中间体也已被披露。