(S)-(-)-α-烯丙基丙氨酸 | 96886-55-4

• 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)-(-)-α-烯丙基丙氨酸
• 中文别名: L-α-烯丙基丙氨酸；(R)-2-氨基-2-甲基-4-戊烯酸；(S)-2-氨基-2-甲基-4-戊烯酸；D-alpha-烯丙基丙氨酸
• 英文名称: (S)-α-allylalanine
• 英文别名: (S)-2-amino-2-methylpent-4-enoic acid；(2S)-2-azaniumyl-2-methylpent-4-enoate
• CAS: 96886-55-4
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: QMBTZYHBJFPEJB-LURJTMIESA-N

物化性质

• 熔点：
  285℃
• 沸点：
  226.2±33.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

SDS

Name:	(S)-(-)-2-Amino-2-Methyl-4-Pentenoic Acid Monohydrate 99+% e.e. Material Safety Data Sheet
Synonym:	L-alpha-Allylalanin
CAS:	96886-55-4

Section 1 - Chemical Product MSDS Name:(S)-(-)-2-Amino-2-Methyl-4-Pentenoic Acid Monohydrate 99+% e.e. Material Safety Data Sheet
Synonym:L-alpha-Allylalanin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
96886-55-4	(S)-(-)-2-Amino-2-Methyl-4-Pentenoic A	>99	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 96886-55-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 283 deg C ( 541.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 283 deg C
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H11NO2.H2O
Molecular Weight: 147.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 96886-55-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-(-)-2-Amino-2-Methyl-4-Pentenoic Acid, Monohydrate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 96886-55-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 96886-55-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 96886-55-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-(-)-α-烯丙基丙氨酸 在 (1,3-dimesitylimidazolidin-2-yl)(PCy₃)benzylidene-RuCl₂ 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 51.0h， 生成 methyl (S)-2-(((benzyloxy)carbonyl)amino)-5-(1,3-dioxolan-2-yl)-2-methylpent-4-enoate
  参考文献：
  名称：

  跨复分解路线的功能化的α-甲基α-取代的氨基酸

  摘要：

  用化学酶方法合成功能化的α-甲基α-取代的氨基酸。这涉及酰胺酶介导的α-甲基α-取代的侧链ω-不饱和氨基酸的酶促拆分，然后通过交叉复分解进行功能化。

  DOI：

  10.1002/adsc.200600446
• 作为产物：
  描述：

  (2R,4S)-2-ferrocenyl-3-pivaloyl-4-allyl-4-methyl-1,3-oxazolidin-5-one 在 amberlyst-15 resin 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 以77%的产率得到(S)-(-)-α-烯丙基丙氨酸
  参考文献：
  名称：

  立体选择性官能化的顺式和反式-2-二茂铁基-3-新戊基-4-烷基-1,3-恶唑烷丁-5-酮：（R）-和（S）-2-烷基-2-氨基戊基-的不对称合成4-烯酸和（2 R，3 S）-2-氨基-2-甲基-3-羟基-3-苯基丙酸†

  摘要：

  用LDA处理一系列顺式和反式-2-二茂铁基-3-新戊酰基-4-烷基-1,3-恶唑烷-5-酮，然后加入烯丙基溴促进在恶唑烷酮环的4-位抗立体定向2-二茂铁基的高度立体选择性烯丙基化（> 98％de）。所得4,4-二取代的恶唑烷酮（> 98％de）的水解在高ee中产生对映体（R）-和（S）-2-烷基-2-氨基戊-4-烯酸。此外，顺式-2-二茂铁基-3-新戊酰基-4-甲基-1,3-恶唑烷-5-苯甲醛然后原位进行O-保护得到> 98％de的O-保护的羟醛产物，并进行水解（2 R，3 S）-2-氨基-2-甲基-3-羟基-3-苯基丙酸 在> 98％de。

  DOI：

  10.1039/b814453b

文献信息

• [EN] INHIBITORS OF HISTONE DEACETYLASE USEFUL FOR THE TREATMENT OR PREVENTION OF HIV INFECTION<br/>[FR] INHIBITEURS D'HISTONE DÉSACÉTYLASE UTILES POUR LE TRAITEMENT OU LA PRÉVENTION D'UNE INFECTION PAR LE VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2020028150A1

  公开（公告）日：2020-02-06

  The present invention relates to Compounds of Formula (I): Formula (I) and pharmaceutically acceptable salts or prodrug thereof, wherein R1, R2, R3, Ra, Rb, A and B are as defined herein. The present invention also relates to compositions comprising at least one compound of Formula (I), and methods of using the compounds of Formula (I) for treating or preventing HIV infection in a subject.

  本发明涉及公式（I）的化合物：公式（I）及其药学上可接受的盐或前药，其中R1、R2、R3、Ra、Rb、A和B如本文所定义。本发明还涉及包含至少一种公式（I）化合物的组合物，以及使用公式（I）化合物治疗或预防受试者的HIV感染的方法。
• Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL. Synthesis of α-methyl amino acids
  作者：Yu. N. Belokon、K. A. Kochetkov、T. D. Churkina、N. S. Ikonnikov、A. A. Chesnokov、O. V. Larionov、H. V. Kagan

  DOI：10.1007/bf02494637

  日期：1999.5

  enantioselective alkylation of Schiff's bases derived from alanine with reactive alkyl halides. Acid hydrolysis of the reaction products affords (R)-α-methylphenyl-alanine, (R)-α-allylalanine, and (R)-α-methylnaphthylalanine in 61–93% yields and withee 69–94%. When (S,S)-TADDOL is used, the (S)-amino acid is formed. A mechanism explaning the observed features of the reaction is proposed.

  结果表明，由 (4R,5R)-2,2-二甲基-1,3-二氧戊环-4,5-双(二苯基甲醇) ((R,R)-TADDOL) 及其一些衍生物形成的醇钠可以用作手性催化剂，用于从丙氨酸衍生的席夫碱与反应性烷基卤化物的对映选择性烷基化。反应产物的酸水解得到 (R)-α-甲基苯基-丙氨酸、(R)-α-烯丙基丙氨酸和 (R)-α-甲基萘丙氨酸，产率为 61-93%，产率为 69-94%。当使用 (S,S)-TADDOL 时，会形成 (S)-氨基酸。提出了解释观察到的反应特征的机制。
• [EN] METATHESIS REACTION INVOLVING THE UNSATURATED SIDE CHAIN OF AN ALPHA, ALPHA-DISUBSTITUTED AMINO ACID<br/>[FR] REACTION DE METATHESE FAISANT APPEL A LA CHAINE LATERALE INSATUREE D'UN ACIDE AMINE ALPHA, ALPHA-DISUBSTITUE
  申请人：DSM IP ASSETS BV

  公开号：WO2004101476A1

  公开（公告）日：2004-11-25

  The invention relates to a process for amino acid synthesis, i.e., the preparation of side chain unsaturated α,α-disubstituted-α-amino acid derivatives with formula (1) wherein: * denotes a stereogenic C-atom PG represents an N-protecting group or the C-terminal part of an optionally protected amino acid or peptide chain; X represents an optionally substituted amine group or an alkoxy group; R1 represents an optionally substituted alkyl group; Ri represents R2 or R3; if Ri = R2 then Rii = R5 and if Ri = R3 then Rii = H; R2, R3 and R5 each independently represent H, an optionally substituted (cyclo)alkyl, (hetero)aryl, acyl, alkoxycarbonyl, cyano, di-alkylphosphonyl, oxiranyl group, a CHO group optionally protected as its acetal, or a group derived from an O-protected carbohydrate, or R2 and R5 may form together with the C-atorn to which they are attached an optionally substituted hydrocarbon ring, with the proviso that R2 , R3 and R5 do not all represent H at the same time. R4 represents H, an alkyl group or an aryl group; n represents an integer larger than or equal to 0, via a cross metathesis reaction between the corresponding amino acid derivative precursor and an (eventually substituted) alkene.

  该发明涉及一种氨基酸合成方法，即制备具有式（1）的侧链不饱和α，α-二取代-α-氨基酸衍生物的过程，其中：*表示一个立体异构的C原子，PG代表一个N保护基团或者一个可选择保护的氨基酸或肽链的C末端部分；X代表一个可选择取代的胺基团或者一个烷氧基团；R1代表一个可选择取代的烷基团；Ri代表R2或R3；如果Ri = R2，则Rii = R5，如果Ri = R3，则Rii = H；R2、R3和R5分别独立地代表H，一个可选择取代的（环）烷基，（杂环）芳基，酰基，烷氧羰基，氰基，二烷基膦基，环氧丙基基团，一个CHO基团，可选择保护为其缩醛基团，或者源自一个O保护的碳水化合物的基团，或者R2和R5可以与它们附着的C原子一起形成一个可选择取代的碳氢环，条件是R2、R3和R5不能同时代表H。R4代表H，一个烷基团或者一个芳基；n代表大于或等于0的整数，通过相应氨基酸衍生物前体与（可能取代的）烯烃之间的交叉甲醇反应。
• Palladium‐Catalyzed Asymmetric Decarboxylative Allylation of Azlactone Enol Carbonates: Fast Access to Enantioenriched α‐Allyl Quaternary Amino Acids
  作者：Massimo Serra、Eric Bernardi、Giorgio Marrubini、Ersilia De Lorenzi、Lino Colombo

  DOI：10.1002/ejoc.201801363

  日期：2019.1.31

  A practical synthetic protocol for the preparation of enantioenriched 4‐allyl oxazol‐5‐ones was developed. The key Pd‐catalyzed decarboxylative allylation allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. The corresponding quaternary amino acids can be recovered in their enantiopure form or in high optical purity after a single recrystallization

  开发了一种实用的合成方案，用于制备对映体富集的4-烯丙基恶唑5-酮。关键的钯催化脱羧烯丙基化使烯丙基化衍生物的收率很高（83-98％），而ee最高可达85％。在单个重结晶步骤后，可以其对映体纯形式或高光学纯度回收相应的季氨基酸。
• Two phenyls are better than one or three: synthesis and application of terminal olefin-oxazoline (TOlefOx) ligands
  作者：Yi-Shuang Zhao、Jian-Kang Liu、Zhi-Tao He、Jing-Chao Tao、Ping Tian、Guo-Qiang Lin

  DOI：10.1039/c6ob00460a

  日期：——

  A novel terminal olefin-oxazoline ligand was introduced into rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to enones and gave excellent enantioselectivities. The two phenyls proved better than one or three in ligand evaluations.

  一种新型的末端烯烃-恶唑啉配体被引入到铑催化的芳基硼酸与烯酮的不对称共轭加成中，并具有出色的对映选择性。在配体评估中，证明两个苯基优于一个或三个。