N-乙酰-DL-苯丙氨酸 | 2901-75-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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-DL-苯丙氨酸
• 中文别名: N-乙酰基-DL-苯丙氨酸；阿丙氨酸
• 英文名称: (R,S)-N-acetyl phenylalanine
• 英文别名: N-acetylphenylalanine；2-acetamido-3-phenylpropionic acid；Ac-dl-Phe-OH；Afalanine；2-acetamido-3-phenylpropanoic acid
• CAS: 2901-75-9
• 化学式: C₁₁H₁₃NO₃
• mdl: MFCD00063157
• 分子量: 207.229
• InChiKey: CBQJSKKFNMDLON-UHFFFAOYSA-N

物化性质

• 熔点：
  152.0 to 156.0 °C
• 沸点：
  453.9±38.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)
• 最大波长(λmax)：
  280nm(lit.)
• 碰撞截面：
  149.4 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090
• 储存条件：
  请将密封保存。存储在干燥阴凉处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Acetyl-DL-phenylalanine
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: N-Acetyl-DL-phenylalanine
CAS number: 2901-75-9

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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: C11H13NO3
Molecular weight: 207.2

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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

制备方法与用途

生物活性

Afalanine（N-乙酰-DL-苯丙氨酸）是一种抗抑郁药。

用途

用于治疗抑郁症。

反应信息

• 作为反应物：
  描述：

  N-乙酰-DL-苯丙氨酸 在 氢溴酸 作用下， 生成 L-苯丙氨酸
  参考文献：
  名称：

  The Resolution of Amino Acids. I. Phenylalanine and Valine¹

  摘要：

  DOI：

  10.1021/ja01151a110
• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸 在 α-苯乙胺 作用下， 以 various solvent(s) 为溶剂， 生成 N-乙酰-DL-苯丙氨酸
  参考文献：
  名称：

  Racemization of Optically Active AromaticN-Acetylamino Acids and Asymmetric Transformation ofN-Acetyl-2-(4-hydroxyphenyl)glycine via Salt Formation with Optically Active α-Methylbenzylamine

  摘要：

  以(RS)-α-甲基苄胺[(RS)-MBA]作为碱催化剂，测定了N-乙酰基-(S)-酪氨酸、N-乙酰基-(S)-苯丙氨酸、N-乙酰基-(R)-2-(4-羟基苯基)甘氨酸[(R)-AcHpg]、N-乙酰基-(R)-2-苯基甘氨酸和N-乙酰基-(S)-丙氨酸的消旋化速率。消旋化的速率常数（一级反应速率常数）通常随N-乙酰氨基酸侧链极性取代常数的增加而增加。消旋化过程似乎受侧链诱导效应的影响。基于消旋化结果，利用(R)-MBA对(RS)-AcHpg进行不对称转换，通过连续使用滤液作为溶剂，得到了光学纯的(R)-AcHpg与(R)-MBA的盐。从盐中分离光学纯的(R)-2-(4-羟基苯基)甘氨酸[(R)-Hpg]，基于起始的(RS)-AcHpg，产率为87-90%。此外，使用(S)-MBA实现了(R)-AcHpg的不对称转换，经(S)-AcHpg与(S)-MBA盐的纯化并随后水解，得到了产率为80%的光学纯(S)-Hpg。

  DOI：

  10.1246/bcsj.65.965
• 作为试剂：
  描述：

  甲基丁胺 、 (Z)-4-(3-trimethylsilylprop-2-ynoxy)but-2-en-1-ol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 N-乙酰-DL-苯丙氨酸 、 氢气 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.25h， 以53%的产率得到butyl-methyl-(2-{4-[1-trimethylsilanyl-meth-(Z)-ylidene]-tetrahydro-furan-3-yl}-ethyl)amine
  参考文献：
  名称：

  A Sequential Palladium-Catalyzed Alder-Ene-Reductive Amination Reaction

  摘要：

  Alkyne allyl alcohols are readily transformed into beta-amino ethyl alkylidene tetrahydrofurans or beta-amino ethyl alkylidene pyrrolidines in a Pd-catalyzed cycloisomerization-reductive amination sequence with remarkable chemoselectivity leaving benzyl groups and trisubstituted double bonds intact.

  DOI：

  10.1021/ol050674k

文献信息

• Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor
  作者：Steven P. Cummings、Thanh-Ngoc Le、Gilberto E. Fernandez、Lorenzo G. Quiambao、Benjamin J. Stokes

  DOI：10.1021/jacs.6b02132

  日期：2016.5.18

  There are few examples of catalytic transfer hydrogenations of simple alkenes and alkynes that use water as a stoichiometric H or D atom donor. We have found that diboron reagents efficiently mediate the transfer of H or D atoms from water directly onto unsaturated C-C bonds using a palladium catalyst. This reaction is conducted on a broad variety of alkenes and alkynes at ambient temperature, and boric

  使用水作为化学计量的 H 或 D 原子供体的简单烯烃和炔烃的催化转移氢化的例子很少。我们发现二硼试剂使用钯催化剂有效地介导了 H 或 D 原子从水中直接转移到不饱和 CC 键上。该反应在环境温度下对多种烯烃和炔烃进行，硼酸是唯一的副产物。机理实验表明，该反应是通过从水中的氢原子转移生成 Pd 氢化物中间体而实现的。重要的是，还实现了从化学计量的 D2O 中完全掺入氘。
• Phosphoric Acid Mediated Light‐Induced Minisci C−H Alkylation of <i>N</i> ‐Heteroarenes
  作者：Songyang Jin、Xinxin Geng、Yujun Li、Ke Zheng

  DOI：10.1002/ejoc.202001538

  日期：2021.2.12

  A visible light‐intduced/phosphate‐mediated light‐induced Minisci‐type reaction under metal‐ and photocatalyst‐free condition was developed, which provided an efficient and environmentally friendly way to access functionalized N‐heteroarenes. The transformation underwent a radical pathway, and the diphenyl phosphate played a key role in the catalytic cycle via hydrogen bonding.

  在无金属和无光催化剂的条件下，开发了可见光诱导/磷酸盐介导的光致Minisci型反应，这为获得功能化的N-杂芳烃提供了一种有效且环保的方法。转化经历了自由基途径，而磷酸二苯酯通过氢键在催化循环中起着关键作用。
• C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin
  申请人：Bao Jian

  公开号：US20050228190A1

  公开（公告）日：2005-10-13

  Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C 1 -symmetric bisphosphine ligands bound to transition metals.

  通过对原生手性烯烃进行对映选择性加氢制备(S)-(+)-3-(氨甲基)-5-甲基己酸及其结构相关化合物的材料和方法已被披露。这些方法采用了新颖的手性催化剂，其中包括与过渡金属结合的C1对称双膦配体。
• N-carbamoyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidines(CAPP). Efficient new chiral ligands for asymmetric hydrogenation
  作者：Iwao Ojima、Noriko Yoda

  DOI：10.1016/s0040-4039(00)78836-8

  日期：1980.1

  N-(N′-substituted carbamoyl)-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidines (CAPP) was prepared, which exhibited excellent stereoselectivity in the asymmetric hydrogenation of α-acetamidocinnamic acid derivatives and itaconic acid as chiral ligand of the rhodium(I) catalyst.

  制备了一系列的N-（N'-取代的氨基甲酰基）-4-二苯基膦基-2-二苯基膦基甲基吡咯烷酮（CAPP），它们在作为铑的手性配体的α-乙酰氨基doc酰胺酸衍生物和衣康酸的不对称加氢中表现出优异的立体选择性。 I）催化剂。
• [EN] GRANZYME B DIRECTED IMAGING AND THERAPY<br/>[FR] IMAGERIE DU GRANZYME B ET THÉRAPIE DIRIGÉES CONTRE LE GRANZYME B
  申请人：CYTOSITE BIOPHARMA INC

  公开号：WO2019160916A1

  公开（公告）日：2019-08-22

  Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

  本文提供了用于成像Granzyme B的杂环化合物。还提供了成像Granzyme B的方法、联合疗法以及包含Granzyme B成像试剂的试剂盒。