N-乙酰基-O-甲基-L-酪氨酸甲酯 | 17355-24-7

• 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-乙酰基-O-甲基-L-酪氨酸甲酯
• 英文名称: (S)-N-acetyl-3-(4-methoxyphenyl)alanine methyl ester
• 英文别名: methyl (S)-2-acetamido-3-(4-methoxyphenyl)propanoate；(S)-methyl 2-acetamido-3-(4-methoxyphenyl)propanoate；methyl (S)-2-acetamido-3-(4-methoxyphenyl)propionate；methyl (S)-2-(acetylamino)-3-(4-methoxyphenyl)propanoate；methyl (2S)-2-acetamido-3-(4-methoxyphenyl)propanoate
• CAS: 17355-24-7
• 化学式: C₁₃H₁₇NO₄
• mdl: MFCD00069961
• 分子量: 251.282
• InChiKey: HCLXPKBWRUCQAF-LBPRGKRZSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  428.6±35.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-tyr(me)-ome
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Ac-tyr(me)-ome
CAS number: 17355-24-7

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H17NO4
Molecular weight: 251.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 2-acetylamino-3-(4-methoxyphenyl)propanoate	70529-50-9	C13H17NO4	251.282
  N-乙酰-L-酪氨酸甲酯	N-acetyl-L-tyrosine methyl ester	2440-79-1	C12H15NO4	237.255
  N-乙酰基-O-甲基-L-酪氨酸	(S)-N-acetyl-p-methoxyphenylalanine	28047-05-4	C12H15NO4	237.255
  N-乙酰-L-酪氨酸	N-acetyl-L-tyrosine	537-55-3	C11H13NO4	223.229
  4-甲氧基-L-苯丙氨酸	O-Methyltyrosine	6230-11-1	C10H13NO3	195.218

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  N-乙酰基-O-甲基-L-酪氨酸	(S)-N-acetyl-p-methoxyphenylalanine	28047-05-4	C12H15NO4	237.255
  ——	methyl (2S)-2-acetamido-3-(3-formyl-4-methoxyphenyl)propanoate	37466-31-2	C14H17NO5	279.293
  ——	N-[(1S)-2-hydroxy-1-(4-methoxybenzyl)ethyl]acetamide	855594-70-6	C12H17NO3	223.272

反应信息

• 作为反应物：
  描述：

  N-乙酰基-O-甲基-L-酪氨酸甲酯 生成 N-acetyl-O-methyl-L-tyrosinamide
  参考文献：
  名称：

  Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations

  摘要：

  The photophysical properties of tyrosine and its derivatives with free and blocked functional groups in water were studied by steady-state and time-resolved fluorescence spectroscopy and global analysis. Tyrosine fluorescence intensity decays in water at pH = 5.5 in the short-wavelength region (290-320 nm) are monoexponential, whereas, at longer wavelengths, they are biexponential. The monoexponential fluorescence intensity decay of O-methyl tyrosine across the fluorescence band is observed. The fluorescence lifetimes of Tyr calculated using a global analysis are equal to 3.37 +/- 0.04 ns at the short-wavelength region and 0.98 +/- 0.12 ns at the longer-wavelength region. This observation, together with the decay-associated spectra, indicate that the short-lifetime component can be attributed to tyrosine with phenol hydroxyl groups hydrogen-bonded with water molecules. The rotamer populations calculated from potentials of mean forces, as well as those obtained from H-1 NMR spectroscopy, do not correspond to the pre-exponential factors obtained from fluorescence spectroscopy. The calculated energy barriers of rotations about the C-alpha-C-beta bond indicate that the interconversion rate constant for tyrosine and N-acetyl-tyrosinamide are much greater than the fluorescence rate constant. Monoexponential fluorescence intensity decay of tyrosine derivatives in acetonitrile solution is observed for all derivatives studied and, contrary to the aqueous solution, the amide group does not quench the fluorescence. Thus, specific conformation(s) stabilized by the hydrogen-bond network seem to be responsible for the heterogeneous fluorescence intensity decay of tyrosine derivatives in aqueous solution.

  DOI：

  10.1021/jp036721c
• 作为产物：
  描述：

  4-甲氧基-L-苯丙氨酸 在 水 作用下， 生成 N-乙酰基-O-甲基-L-酪氨酸甲酯
  参考文献：
  名称：

  Felix et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1952, vol. 291, p. 24,28

  摘要：

  DOI：

文献信息

• Modular Monodentate Phosphoramidite Ligands for Rhodium-Catalyzed Enantioselective Hydrogenation
  作者：Yan Liu、Kuiling Ding

  DOI：10.1021/ja052749l

  日期：2005.8.1

  A new class of monodentate phosphoramidite ligands (DpenPhos) has been developed on the basis of the modular concept for Rh(I)-catalyzed asymmetric hydrogenations of a variety of olefin derivatives, affording the corresponding optically active compounds in excellent yields and enantioselectivities. The ligands have the advantages of facile preparation, tunable structure, and broad scope of substrates

  基于 Rh(I) 催化的各种烯烃衍生物的不对称氢化的模块化概念，开发了一类新的单齿亚磷酰胺配体 (DpenPhos)，以优异的产率和对映选择性提供相应的光学活性化合物。这些配体在其 Rh(I) 络合物催化的不对称氢化中具有制备容易、结构可调和底物范围广等优点。
• Synthesis of Chiral Hydroxyl Phospholanes from <scp>d</scp>-mannitol and Their Use in Asymmetric Catalytic Reactions
  作者：Wenge Li、Zhaoguo Zhang、Dengming Xiao、Xumu Zhang

  DOI：10.1021/jo000066c

  日期：2000.6.1

  Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis-Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino

  手性羟基一膦3 [（2S，3S，4S，5S）-3,4-二羟基-2，5-二甲基-1-苯基膦烷]和双膦酸酯5a [1,2-双[（2S，3S，4S，5S） -3,4-二羟基-2,5-二甲基磷杂环戊烷基]苯]和5b [1,2-双[（2S，3S，4S，5S）-2,5-二乙基-3,4-二羟基磷杂环戊基]苯]从现成的D-甘露醇中以高收率获得。已经研究了在膦存在下保护和脱保护OH-基团的策略。当使用羟基膦作为催化剂时，在Baylis-Hillman反应中观察到速率加速。铑与手性双膦酸酯的络合物是高度对映选择性的催化剂，用于各种官能化烯烃（如脱氢氨基酸衍生物，衣康酸衍生物和烯酰胺）的不对称氢化。
• A Novel Chiral Ferrocenyl Phosphine Ligand from Sugar:  Applications in Rh-Catalyzed Asymmetric Hydrogenation Reactions
  作者：Duan Liu、Wenge Li、Xumu Zhang

  DOI：10.1021/ol0269998

  日期：2002.12.1

  [structure: see text] A new chiral ferrocenyl diphosphine ligand 3 was synthesized from readily available D-mannitol. Rh-complex with this ligand showed high enantioselectivity and reactivity in the asymmetric hydrogenation of dehydroamino acid derivatives and itaconic acid derivatives. Up to over 99% ee and 10 000 TON were achieved with this catalytic system.

  [结构：见正文]从容易获得的D-甘露糖醇合成了新的手性二茂铁基二膦配体3。具有这种配体的Rh-络合物在脱氢氨基酸衍生物和衣康酸衍生物的不对称氢化中显示出高的对映选择性和反应性。使用该催化系统可实现高达99％的ee和10000吨。
• A Metal‐Free Direct Arene C−H Amination
  作者：Tao Wang、Marvin Hoffmann、Andreas Dreuw、Edina Hasagić、Chao Hu、Philipp M. Stein、Sina Witzel、Hongwei Shi、Yangyang Yang、Matthias Rudolph、Fabian Stuck、Frank Rominger、Marion Kerscher、Peter Comba、A. Stephen K. Hashmi

  DOI：10.1002/adsc.202100236

  日期：2021.6.8

  The synthesis of aryl amines via the formation of a C−N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C−H amination using hydroxylamine derivatives under benign

  通过形成 CN 键合成芳胺是制备功能材料、活性药物成分和生物活性产品的重要工具。通常，这种化学连接只能通过过渡金属催化的反应、光化学或电化学来实现。在这里，我们报告了在良性条件下使用羟胺衍生物进行的无金属芳烃 C-H 胺化。即使在存在各种官能团的情况下，胺化试剂 TsONHR 和芳烃底物之间的电荷转移相互作用也能实现芳烃的化学选择性胺化。氧气对于有效转化至关重要，其对电子转移步骤的加速作用已通过实验证明。此外，
• BABIPhos Family of Biaryl Dihydrobenzooxaphosphole Ligands for Asymmetric Hydrogenation
  作者：Guisheng Li、Olga V. Zatolochnaya、Xiao-Jun Wang、Sonia Rodríguez、Bo Qu、Jean-Nicolas Desrosiers、Hari P. R. Mangunuru、Soumik Biswas、Daniel Rivalti、Shuklendu D. Karyakarte、Joshua D. Sieber、Nelu Grinberg、Ling Wu、Heewon Lee、Nizar Haddad、Daniel R. Fandrick、Nathan K. Yee、Jinhua J. Song、Chris H. Senanayake

  DOI：10.1021/acs.orglett.8b00139

  日期：2018.4.6

  Novel bidentate phosphine ligands BABIPhos featuring a biaryl bis-dihydrobenzooxaphosphole core are presented. Their synthesis was achieved via Pd-catalyzed reductive homocoupling of dihydrobenzooxaphosphole aryl triflates. An efficient route toward various analogues was also established, giving access to phosphines with different electronic and steric properties. The newly obtained ligands demonstrated

  提出了具有联芳基双-二氢苯并恶唑膦核的新型双齿膦配体BABIPhos。它们的合成是通过Pd催化的二氢苯并氧杂磷酰基芳基三氟甲磺酸酯的还原均偶联来实现的。还建立了通往各种类似物的有效途径，从而获得了具有不同电子和空间特性的膦。新获得的配体在Rh催化的二取代和三取代的酰胺的不对称加氢中显示出高效率和选择性。这类新的配体是对先前描述的双齿苯并恶唑磷配体BIBOP的补充。