N-(三氟乙酰基)-L-酪氨酸甲酯 | 1604-54-2

• 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-(三氟乙酰基)-L-酪氨酸甲酯
• 英文名称: N-trifluoroacetyl-L-tyrosine methyl ester
• 英文别名: methyl (2,2,2-trifluoroacetyl)-L-tyrosinate；N-Trifluoracetyl-L-tyrosin-methylester；methyl (2S)-3-(4-hydroxyphenyl)-2-[(2,2,2-trifluoroacetyl)amino]propanoate
• CAS: 1604-54-2
• 化学式: C₁₂H₁₂F₃NO₄
• mdl: MFCD00056680
• 分子量: 291.227
• InChiKey: RPUGHMMKNNBUQA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : N-Trifluoroacetyl-L-tyrosine methyl ester
CAS-No. : 1604-54-2
Specific use(s) : no data available

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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]
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C12H12F3NO4
Molecular Weight : 291,22 g/mol
Component Concentration
N-Trifluoroacetyl-L-tyrosine methyl ester
CAS-No. 1604-54-2 -

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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
Flush eyes with water as a precaution.
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 immediate medical attention and special treatment needed
no data available

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Section 5. FIRE-FIGHTING 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), Hydrogen fluoride
Precautions for fire-fighters
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. 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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
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
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
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
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.
Body Protection
Complete suit protecting against chemicals, 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: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting/freezing point no data available
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: 2,158
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
no data available
Hazardous decomposition products

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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 Harmful if swallowed.
Skin
May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause 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. 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 users
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-(三氟乙酰基)-L-酪氨酸甲酯 在 氧气 、 copper diacetate 、 potassium hydroxide 作用下， 以 甲醇 、 aq. phosphate buffer 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 51.0h， 生成 L-酪氨酸
  参考文献：
  名称：

  从反式环辛烯的点击发布：从已建立的氨基甲酸酯到显着的醚裂解的机理分析和范围扩展

  摘要：

  与四嗪反应后，可从反式-环辛烯（TCO）进行生物正交裂解的烯丙基氨基甲酸酯。我们在本文中公开了该反应还可以裂解TCO酯，碳酸酯和令人惊奇的醚。机理研究表明，消除主要是由迅速消除的1,4-二氢哒嗪互变异构体的形成决定的，而较少取决于离去基团的性质。与广泛使用的p相反-氨基苄氧基连接基，可裂解芳族醚，但不裂解脂族醚，芳族，苄基和脂族TCO醚的裂解效率与氨基甲酸酯，碳酸酯和酯一样。快速解开血清中TCO掩盖的酪氨酸，然后酪氨酸酶氧化，证明了生物正交醚的释放。最后，酪氨酸解笼用于化学控制无酪氨酸培养基中的细胞生长。

  DOI：

  10.1002/anie.201800402
• 作为产物：
  描述：

  L-酪氨酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 N-(三氟乙酰基)-L-酪氨酸甲酯
  参考文献：
  名称：

  一种L-酪氨酸衍生物的制备方法

  摘要：

  本发明公开了一种L‑酪氨酸衍生物的制备方法，所述L‑酪氨酸衍生物是O‑烷基‑N‑[芴甲氧羰基]‑L‑酪氨酸，其是以L‑酪氨酸为起始原料，依次经酯化、酰胺化、醚化/水解、酰胺化制得O‑烷基‑N‑[芴甲氧羰基]‑L‑酪氨酸，目标产物的总收率可达61.5%，ee值可达99%以上。本发明的制备方法中，具有原料廉价易得、成本较低等优点，例如醚化反应避免了三苯基氧磷的分离；具有工艺简单、路线较短、反应条件温和等优点，例如醚化和水解采用一锅法；整个工艺过程产生的三废少，产物收率和纯度较高，适于工业化生产。

  公开号：

  CN112920086B

文献信息

• Direct, visible light-sensitized benzylic C H fluorination of peptides using dibenzosuberenone: selectivity for phenylalanine-like residues
  作者：Desta Doro Bume、Cody Ross Pitts、Rayyan Trebonias Jokhai、Thomas Lectka

  DOI：10.1016/j.tet.2016.08.018

  日期：2016.10

  A visible light-sensitized benzylic sp3 CH fluorination protocol using dibenzosuberenone (5 mol %) and Selectfluor® is optimized for the direct functionalization of phenylalanine-like residues in short chain peptides. Amino acids, dipeptides, and tripeptides undergo benzylic fluorination with remarkable regioselectivity in the presence of protected basic, acidic, and nonpolar side chains (including

  可见光敏化苄SP 3 Ç ħ氟化使用dibenzosuberenone（5摩尔％）和的Selectfluor协议®为苯丙氨酸样在短链肽的残基的直接官能优化。在受保护的碱性，酸性和非极性侧链（包括具有叔位的侧链）存在下，氨基酸，二肽和三肽会经历显着的区域选择性的苄基氟化反应。此外，还探讨了保护基团的兼容性，克规模应用和竞争实验。
• Photorelease of tyrosine from a-carboxy-6-nitroveratryl (aCNV) derivatives
  作者：Alexander G. Russell、Matthew J. Sadler、Helen J. Laidlaw、Agustín Gutiérrez-Loriente、Christopher W. Wharton、David Carteau、Dario M. Bassani、John S. Snaith

  DOI：10.1039/c2pp05320a

  日期：2012.3

  The synthesis of photolabile tyrosine derivatives protected on the phenolic oxygen by the α-carboxy-6-nitroveratryl (αCNV) protecting group is described. The compounds undergo rapid photolysis at wavelengths longer than 300 nm to liberate the corresponding phenol in excellent yield (quantum yield for the deprotection of tyrosine = 0.19). Further protection of caged tyrosine is possible, yielding N-Fmoc protected derivatives suitable for direct incorporation of caged tyrosine in solid-phase peptide synthesis.

  报道了通过α-羧基-6-硝基藜芦基（αCNV）保护基保护在酚羟基上的光不稳定性酪氨酸衍生物的合成。这些化合物在波长大于300 nm的光照射下迅速发生光解反应，以优异的产率释放相应的苯酚（酪氨酸去保护的量子产率为0.19）。还可以对笼蔽的酪氨酸进行进一步保护，得到适合直接用于固相肽合成的N-芴甲氧羰基保护衍生物。
• Stereocontrolled glycoside synthesis by activation of glycosyl sulfone donors with scandium(<scp>iii</scp>) triflate
  作者：Amandine Xolin、Romain Losa、Aicha Kaid、Cédric Tresse、Jean-Marie Beau、François-Didier Boyer、Stéphanie Norsikian

  DOI：10.1039/c7ob02792c

  日期：——

  The activation of aryl glycosyl sulfone donors has been achieved using scandium(III) triflate and has led to the selective preparation of α-mannosides resulting from a post-glycosylation anomerization.

  使用三氟甲磺酸scan （III）已经实现了芳基糖基砜供体的活化，并导致了由糖基化后的异构化反应产生的α-甘露糖苷的选择性制备。
• Synthetic methodology towards allylic<i>trans</i>-cyclooctene-ethers enables modification of carbohydrates: bioorthogonal manipulation of the<i>lac</i>repressor
  作者：Mark A. R. de Geus、G. J. Mirjam Groenewold、Elmer Maurits、Can Araman、Sander I. van Kasteren

  DOI：10.1039/d0sc03216f

  日期：——

  The inverse electron-demand Diels–Alder (IEDDA) pyridazine elimination is one of the key bioorthogonal bond-breaking reactions. In this reaction trans-cyclooctene (TCO) serves as a tetrazine responsive caging moiety for amines, carboxylic acids and alcohols. One issue to date has been the lack of synthetic methods towards TCO ethers from functionalized (aliphatic) alcohols, thereby restricting bioorthogonal

  逆电子需求的Diels–Alder（IEDDA）哒嗪消除是关键的生物正交键断裂反应之一。在该反应中，反式-环辛烯（TCO）作为胺，羧酸和醇的四嗪响应笼蔽部分。迄今为止的一个问题是缺乏从官能化的（脂族）醇制备TCO醚的合成方法，从而限制了生物正交的利用。开发了两种新型试剂，可控制顺式-环辛烯（CCO）醚的形成，然后进行优化的光化学异构化以获得TCO醚。该方法以大肠杆菌中lac操纵子系统的受控生物正交激活为例 使用TCO醚修饰的碳水化合物诱导剂。
• Photochemical trifluoromethylation of tyramine and L-tyrosine derivatives
  作者：Kenneth L. Kirk、Mazakazu Nishida、Shozo Fujii、Hiroshi Kimoto

  DOI：10.1016/s0022-1139(00)82410-0

  日期：1992.11

  Ultraviolet irradiation (254 nm) of methanolic solutions of trifluoromethyl iodide (CF3I) in the presence of side-chain-protected tyramine and L-tyrosine results in trifluoromethylation of the aromatic ring. The presence of an amine base to neutralize HI formed during the reaction is essential. The electrophilic trifluoromethyl radical preferentially attacks the ring ortho to the phenolic group, and 3-trifluoromethyltyramine

  在侧链保护的酪胺和L-酪氨酸的存在下，对三氟甲基碘（CF 3 I ）的甲醇溶液进行紫外线照射（254 nm）导致芳环的三氟甲基化。胺碱的存在对中和反应过程中形成的HI是必不可少的。亲电子三氟甲基自由基优先攻击邻位至酚基的环，得到3-三氟甲基酪胺和3-三氟甲基-L-酪氨酸衍生物，产率分别为27％和33％。