(S)-3-氨基-3-苯基丙酸 | 40856-44-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 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: (S)-3-氨基-3-苯基丙酸
• 中文别名: S-3-氨基-3-苯基丙酸,S-beta-苯丙氨酸；S-beta-苯丙氨酸
• 英文名称: (S)-3-amino-3-phenylpropanoic acid
• 英文别名: (S)-3-amino-3-phenylpropionic acid；(S)-β-phenylalanine；(S)-β-Phenyl-β-alanine；(S)-β-amino-β-phenylpropionic acid；(S)-(-)-3-Phenyl-3-aminopropionic acid；(3S)-3-azaniumyl-3-phenylpropanoate
• CAS: 40856-44-8
• 化学式: C₉H₁₁NO₂
• mdl: MFCD01076238
• 分子量: 165.192
• InChiKey: UJOYFRCOTPUKAK-QMMMGPOBSA-N

物化性质

• 熔点：
  251-253 °C(Solv: water (7732-18-5); acetone (67-64-1))
• 沸点：
  307.5±30.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于酸性水溶液（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-3-Amino-3-phenylpropionic acid
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: (S)-3-Amino-3-phenylpropionic acid
CAS number: 40856-44-8

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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: C9H11NO2
Molecular weight: 165.2

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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

(S)-3-氨基-3-苯基丙酸不仅具有消炎作用，还能有效预防蛋白质变性与聚集，并具备高效的保湿功能及清除自由基的能力。因此，它在生物医学领域展现出极大的开发潜力。

反应信息

• 作为反应物：
  描述：

  (S)-3-氨基-3-苯基丙酸 在 硼烷四氢呋喃络合物 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 (S)-3-氧代-1-苯基丙基氨基甲酸叔丁酯
  参考文献：
  名称：

  构型稳定的（S）-和（R）-α-甲基脯氨酸衍生的配体，可直接化学拆分游离的未保护的β3-氨基酸

  摘要：

  一系列nonracemizable配体被用于对各种未保护β的直接化学合成的分辨率3 -氨基酸高对映选择性和产率。获得的一种游离的对映体纯净的β-氨基酸可以直接用作合成抗HIV药物maraviroc的原料，分6步，总收率为49％。

  DOI：

  10.1002/ejoc.201800120
• 作为产物：
  描述：

  (3S)-3-氨基-3-苯基丙酸叔丁酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以96%的产率得到(S)-3-氨基-3-苯基丙酸
  参考文献：
  名称：

  平行合成手性β-氨基酸

  摘要：

  使用高手性锂N-苄基-N-（α-甲基苄基）酰胺的共轭加成，完成了对映体纯度高的30个β-氨基酸阵列的平行不对称合成。该协议的实验简单性和高度实用性通过高15种α，β-不饱和酯的高效平行转化为相应β-氨基酸的对映体系列以高总收率和选择性进行了证明，且每个步骤的纯化步骤最少反应方案。

  DOI：

  10.1016/j.tetasy.2007.06.008
• 作为试剂：
  描述：

  N-苯基马来酰亚胺 、 2-甲基戊醛 在 (S)-3-氨基-3-苯基丙酸 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以98%的产率得到
  参考文献：
  名称：

  α，α-二取代醛与马来酰亚胺的不对称迈克尔加成反应导致氨基酸催化内酯的一锅对映选择性合成

  摘要：

  据报道便宜和快速地构建了取代的琥珀酰亚胺的两种对映体。发现α-或β-氨基酸，如β-苯丙氨酸和α-叔丁基天冬氨酸，是用于α，α-二取代的醛与马来酰亚胺之间反应的有效有机催化剂。使用低催化剂负载量（0.5-3.5％），可以以高产量到定量产量和出色的选择性获得包含连续的四级-三级立体异构中心的产品。最后，描述了一锅高效内酯的不对称合成。

  DOI：

  10.1021/ol4008662

文献信息

• Glutamate as an Efficient Amine Donor for the Synthesis of Chiral β‐ and γ‐Amino Acids Using Transaminase
  作者：Geon‐Hee Kim、Hyunwoo Jeon、Taresh P. Khobragade、Mahesh D. Patil、Sihyong Sung、Sanghan Yoon、Yumi Won、Sharad Sarak、Hyungdon Yun

  DOI：10.1002/cctc.201802048

  日期：2019.3.6

  A recyclable glutamate amine donor system employing transaminase (TA), glutamate dehydrogenase (GluDH) and mutant formate dehydrogenase (FDHm) was developed, wherein amine donor Glu was regenerated using GluDH and thereby circumvented the inhibition of TA by α‐ketoglutarate. Various enantiopure β‐, γ‐amino acids, and amines were successfully synthesized with high conversions and excellent enantiomeric

  开发了一种利用转氨酶（TA），谷氨酸脱氢酶（GluDH）和突变型甲酸脱氢酶（FDHm）的可回收谷氨酸胺供体系统，其中使用GluDH再生了胺供体Glu，从而避免了α-酮戊二酸对TA的抑制作用。使用该系统成功合成了各种对映体纯的β-，γ-氨基酸和胺，具有高转化率和出色的对映体过量。
• New Chiral Derivatizing Agents: Convenient Determination of Absolute Configurations of Free Amino Acids by ¹H NMR
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/ol8028719

  日期：2009.2.19

  The chiral carbonate reagents 5 allow for the direct and unambiguous determination of the absolute configurations of a wide range of free amino acids using 1H NMR. By using a ∼3:1 mixture of (S)-5 and (R)-5, absolute configurations of the corresponding carbamates are determined by only analyzing the nitrogen protons.

  手性碳酸酯试剂5允许使用1 H NMR直接和明确地确定各种游离氨基酸的绝对构型。通过使用〜（S）-5和（R）-5的〜3：1混合物，仅通过分析氮质子即可确定相应氨基甲酸酯的绝对构型。
• Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: A highly enantioselective route to β-amino acids
  作者：Ismail Ibrahem、Ramon Rios、Jan Vesely、Gui-Ling Zhao、Armando Córdova

  DOI：10.1039/b613410f

  日期：——

  The highly chemo- and enantioselective organocatalytic tandem reaction between N-protected hydroxyl amines and α,β-unsaturated aldehydes is presented; the reaction provides access to 5-hydroxyisoxazolidines and β-amino acids in high yields and with 90–99% ee.

  介绍了高度化学选择性和对映选择性的有机催化串联反应，该反应涉及N-保护的羟胺与α,β-不饱和醛的反应；该反应能够以高产率和高对映选择性（90-99% ee）合成5-羟基异恶唑烷和β-氨基酸。
• ENANTIOSELECTIVE ACYLATION OF β-PHENYLALANINE ACID AND ITS DERIVATIVES CATALYZED BY PENICILLIN G ACYLASE FROM<i>Alcaligenes faecalis</i>
  作者：Dengchao Li、Lilian Ji、Xinfeng Wang、Dongzhi Wei

  DOI：10.1080/10826068.2012.719847

  日期：2013.1.15

  This study developed a simple, efficient method for producing racemic β-phenylalanine acid (BPA) and its derivatives via the enantioselective acylation catalyzed by the penicillin G acylase from Alcaligenes faecalis (Af-PGA). When the reaction was run at 25°C and pH 10 in an aqueous medium containing phenylacetamide and BPA in a molar ratio of 2:1, 8 U/mL enzyme and 0.1 M BPA, the maximum BPA conversion

  这项研究开发了一种简单，有效的方法，该方法可通过粪便产碱杆菌（Af-PGA）中的青霉素G酰基转移酶催化对映选择性酰化来生产外消旋β-苯丙氨酸（BPA）及其衍生物。当反应在25：C和pH 10的水介质中以2：1摩尔比，8 U / mL酶和0.1 M的苯乙酰胺和BPA进行时BPA在40分钟时的最大BPA转化效率仅达到36.1％，但是，当pH值和苯乙酰胺与BPA的摩尔比分别提高到11和3：1时，BPA的最高转化效率提高到42.9％。在相对最佳的反应条件下，BPA衍生物的最大转化率在相对较短的反应时间（45-90分钟）内都达到了约50％。产物的对映体过量值（ee p ）和底物的对映体过量值（ee s ）均分别高于98％和95％。这些结果表明，本研究中建立的方法是实用，有效且对环境有益的，可用于对映体纯的BPA及其衍生物的工业生产。
• BENZENESULFONAMIDE COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS
  申请人：Xenon Pharmaceuticals Inc.

  公开号：US20180162868A1

  公开（公告）日：2018-06-14

  This invention is directed to benzenesulfonamide compounds, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of diseases or conditions associated with voltage-gated sodium channels, such as epilepsy and/or epileptic seizure disorders.

  这项发明涉及苯磺酰胺化合物，作为其立体异构体、对映异构体、互变异构体或它们的混合物；或其药学上可接受的盐、溶剂合物或前药，用于治疗与电压门控钠通道相关的疾病或症状，如癫痫和/或癫痫发作障碍。