N-(3,5-二硝基苯甲酰)-L-亮氨酸 | 7495-01-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-(3,5-二硝基苯甲酰)-L-亮氨酸
• 英文名称: (S)-N-(3,5-dinitrobenzoyl)leucine
• 英文别名: N-(3,5-dinitrobenzoyl)-(S)-leucine；N-(3,5-dinitrobenzoyl)-L-leucine；N-(3,5-dinitrobenzoyl)-leucine；N-(3,5-Dinitrobenzoyl)leucine；(2S)-2-[(3,5-dinitrobenzoyl)amino]-4-methylpentanoic acid
• CAS: 7495-01-4
• 化学式: C₁₃H₁₅N₃O₇
• 分子量: 325.278
• InChiKey: DIOBIOPCRMWGAT-NSHDSACASA-N

物化性质

• 熔点：
  186-188 °C(lit.)
• 沸点：
  515.7±50.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  7

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : N-(3,5-Dinitrobenzoyl)-L-leucine
CAS-No. : 7495-01-4
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.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C13H15N3O7 C13H15N3O7
Molecular Weight : 325,27 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, 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
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: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 186 - 188 °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- log Pow: 1,445
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：

  N-(3,5-二硝基苯甲酰)-L-亮氨酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.83h， 生成 N-[(2S)-1-[2-(diethylamino)ethylamino]-4-methyl-1-oxopentan-2-yl]-3,5-dinitrobenzamide
  参考文献：
  名称：

  Tertiary Amine Appended Derivatives of N-(3,5-Dinitrobenzoyl)leucine as Chiral Selectors for Enantiomer Assays by Electrospray Ionization Mass Spectrometry

  摘要：

  合成了手性选择剂N-(3,5-二硝基苯甲酰)亮氨酸的衍生物，并将其用于单阶段电喷雾电离质谱实验中的对映体歧视。设计这些手性选择剂是为了将离子化位点与有效的手性识别所需的位点分离。将一种手性分析物加入到含有两个伪对映体手性选择剂的溶液中，这两个选择剂在绝对立体化学和连接用于通过质子化进行离子化的三级胺位点与其余手性选择剂的绳索长度上有所不同，形成了在电喷雾电离质谱中观察到的选择剂-分析物复合物，其中这些复合物的比例取决于分析物的对映体组成。选择剂-分析物复合物在电喷雾电离质谱中的比例与分析物的对映体组成之间的关系可以用来关联所观察到的对映选择性程度，并进行定量对映体组成的测定。本文还探讨了该方法的适用范围和局限性，并与使用N-(3,5-二硝基苯甲酰)亮氨酸衍生的手性固定相的手性高效液相色谱法观察到的对映选择性进行了比较。

  DOI：

  10.1021/ac050438n
• 作为产物：
  描述：

  L-亮氨酸 、 3,5-二硝基苯甲酰氯 在 methyloxirane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到N-(3,5-二硝基苯甲酰)-L-亮氨酸
  参考文献：
  名称：

  小双分子系统中的手性分子识别：非对映体复合物性质的光谱研究

  摘要：

  练习曲光谱紫外可见，RMN 1 H et effet Overhauser de melanges de propylamide de N-(dinitro-3,5 benzoyl) leucine et de N-(naphtyl-2) alaninate demethyle

  DOI：

  10.1021/ja00254a014

文献信息

• Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans
  作者：Ping Sun、Chunlei Wang、Zachary S. Breitbach、Ying Zhang、Daniel W. Armstrong

  DOI：10.1021/ac902257a

  日期：2009.12.15

  An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic- and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromatic-functionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high “loadability” and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

  首次引入一类不寻常的手性选择剂——环糊精作为键合型手性固定相。与天然环糊精（CFs）相比，其作为手性选择剂的能力相当有限，而脂族和芳族功能化的CF6具有独特且截然不同的对映体选择性。事实上，它们能够分离非常广泛的消旋化合物。特别是，低取代度的脂族衍生化CF6能够基线分离所有测试的手性伯胺。似乎部分衍生化作用于CF6分子会破坏分子内部的氢键，从而使分子核心更易接近。相比之下，高度芳族功能化的CF6固定相在伯胺的对映选择能力方面丧失了大部分能力，但它们对大多数其他类型的分析物获得了广泛的选择性。这类固定相还表现出高“负荷能力”，因此具有在制备分离方面的巨大潜力。对映体选择性的变化通常可以与选择剂的独特结构特征相关联。分离主要在有机溶剂存在下发生。
• Uridine, Thymidine and Inosine Used as Chiral Stationary Phases in HPLC
  作者：Mei Zhang、Min Zi、Bang-Jin Wang、Li-Ming Yuan

  DOI：10.14233/ajchem.2014.15674

  日期：——

  In this paper, we present the first enantioseparations research using thymidine, uridine and inosine as chiral stationary phase bonded to silica gel via 3-(triethoxysilyl)propyl isocyanate in HPLC. Thymidine and uridine chiral stationary phases possess enantioseparation selectivity for alcohols, amines, ketones and carboxylic acids to some degree in normal-phase and reversed-phase mode. This work indicates that nucleoside or deoxynucleoside can be useful for the separation of enantiomers in the liquid phase as a new kind of chiral stationary phase.

  本文中，我们首次报道了利用胸苷、尿苷和次黄嘌呤作为手性固定相，通过3-(三乙氧基硅基)丙基异氰酸酯键合到硅胶上的高效液相色谱法对手性分离的研究。胸苷和尿苷手性固定相在正相和反相模式下具有对醇类、胺类、酮类和羧酸类化合物一定程度的手性分离选择性。这一工作表明，核苷或脱氧核苷可作为液相色谱中分离对映体的一种新型手性固定相。
• Enantioselective reactions using two-component chiral phase transfer catalysts in multiphasic systems
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20030097002A1

  公开（公告）日：2003-05-22

  The present invention provides multiphasic systems comprising at least one chiral selector and an achiral phase transfer catalyst, wherein said system can be used to effect enantioselective reactions or asymmetric induction reactions.

  本发明提供了包含至少一个手性选择剂和一个无手性相转移催化剂的多相系统，其中该系统可用于实现对映选择性反应或不对称诱导反应。
• Continuous Separation of Racemic 3,5-Dinitrobenzoyl-Amino Acids in a Centrifugal Contact Separator with the Aid of Cinchona-Based Chiral Host Compounds
  作者：Andrew J. Hallett、Gerard J. Kwant、Johannes G. de Vries

  DOI：10.1002/chem.200800797

  日期：2009.2.16

  Resolution through revolution: It is possible to extract 3,5‐dinitrobenzoyl‐protected amino acids enantioselectively with the aid of a table‐top centrifugal contact separator and a catalytic amount of a chiral host compound based on the Cinchona alkaloids. Enantioselectivities of up to 80 % could be reached in a single pass. This allows the development of a process for the continuous separation of

  通过旋转解决：借助台式离心接触分离器和催化量的基于金鸡纳生物碱的手性主体化合物，可以对映选择性地提取3,5-二硝基苯甲酰基保护的氨基酸。单次通过可以达到高达80％的对映选择性。这允许开发出连续分离外消旋物的方法。
• 2-Quinoxalinol Salen Compounds and Uses Thereof
  申请人：Gorden Anne E. V.

  公开号：US20090286968A1

  公开（公告）日：2009-11-19

  Disclosed are 2-quinoxalinol salen compounds and in particular 2-quinoxalinol salen Schiff-base ligands. The disclosed 2-quinoxalinol salen compounds may be utilized as ligands for forming complexes with cations, and further, the formed complexes may be utilized as catalysts for oxidation reactions. The disclosed 2-quinoxalinol salen compounds also may be conjugated to solid supports and utilized in methods for selective solid-phase extraction or detection of cations.

  本文披露了2-喹啉醇Salen化合物，特别是2-喹啉醇Salen席夫碱配体。披露的2-喹啉醇Salen化合物可用作与阳离子形成络合物的配体，进而形成的络合物可用作氧化反应的催化剂。披露的2-喹啉醇Salen化合物还可以与固体支撑物结合，并用于选择性固相萃取或阳离子检测方法。