D-苯丙氨酸乙酯盐酸盐 | 63060-94-6

• 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: D-苯丙氨酸乙酯盐酸盐
• 英文名称: D-phenylalanine ethyl ester hydrochloride
• 英文别名: ethyl D-phenylalaninate hydrochloride；ethyl (2R)-2-amino-3-phenylpropanoate;hydrochloride
• CAS: 63060-94-6
• 化学式: C₁₁H₁₅NO₂*ClH
• 分子量: 229.707
• InChiKey: FPFQPLFYTKMCHN-HNCPQSOCSA-N

物化性质

• 熔点：
  153-154 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.3
• 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：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下储存在惰性气体中

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: D-Phenylalanine ethyl ester, HCl
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: D-Phenylalanine ethyl ester, HCl
CAS number: 63060-94-6

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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: C11H15NO2.ClH
Molecular weight: 229.7

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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, hydrogen chloride.

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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

反应信息

• 作为反应物：
  描述：

  D-苯丙氨酸乙酯盐酸盐 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.33h， 生成 N-苄氧羰基-D-苯丙氨酸
  参考文献：
  名称：

  Poststatin, a New Inhibitor of Prolyl Endopeptidase. V. Endopeptidase Inhibitory Activity of Poststatin Analogues.

  摘要：

  合成了30个波杀菌蛋白类似物，并测定了它们对脯氨酰内肽酶、人白细胞弹性蛋白酶和组织蛋白酶B的抑制活性。对内肽酶抑制活性来说，α–酮基非常重要，β–取代–β–氨基–α–氧代丙酸部分的S构型比R构型更为优越。用L–亮氨酸代替波杀菌蛋白中的D–亮氨酸得到的类似物对组织蛋白酶B具有很强的抑制活性。将芳香基团引入到P4位和将脯氨酸引入到P2位使对弹性蛋白酶的抑制活性增强。苄氧羰基–L–高苯丙氨酰–(RS)–3–氨基–2–氧代戊二酰–D–亮氨酰–L–缬氨酸对脯氨酰内肽酶的活性约为天然波杀菌蛋白的6倍。

  DOI：

  10.7164/antibiotics.49.890
• 作为产物：
  描述：

  (3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 在 palladium dichloride 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 22.0h， 生成 D-苯丙氨酸乙酯盐酸盐
  参考文献：
  名称：

  Asymmetric synthesis of monosubstituted and .alpha.,.alpha.-disubstituted .alpha.-amino acids via diastereoselective glycine enolate alkylations

  摘要：

  The enolates derived from the optically active (5S,6R)- and (5R,6S)-4(tert-butyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (1a,b) and (5S,6R)- and (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (2a,b) efficiently couple with alkyl halides to afford the corresponding anti-alpha-monosubstituted oxazinones (3 and 4). The enolate alkylation of the alpha-monosubstituted oxazinones (3 and 4) provides the corresponding alpha,alpha-disubstituted oxazinones (7 and 8). Dissolving-metal reduction of the homologated oxazinones allows the direct preparation of t-BOC-protected alpha-amino acids. In the case of a dissolving-metal-reducible functionality, hydrogenation over a Pd0 catalyst furnishes the zwitterionic amino acids. By employing this protocol several amino acids or their corresponding N-t-BOC derivatives, such as allylglycine, alanine, phenylalanine, beta-ethylaspartic acid, alpha-methylphenylalanine, N-(tert-butyloxycarbonyl)dimethallylglycine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)norvaline, N-(tert-butyloxycarbonyl)-2-(3'-methyl-2'-butenyl)alanine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)alanine, 2-(3'-phenylpropyl)alanine, 2-amino-6-(acetyloxy)hexanoic acid, and 2(tert-butyloxycarbonyl)amino-6-[(p-methoxybenzyl)thio]hexanoic acid, are prepared in high enantiomeric excess.

  DOI：

  10.1021/ja00024a038
• 作为试剂：
  描述：

  甲基叔丁基醚 、 水 、 (2S)-2-氨基-3-苯基丙酸乙酯 、 ethanol hydrochloride 在 magnesium sulfate 、 环己烷 、 D-苯丙氨酸乙酯盐酸盐 作用下， 以 环己烷 为溶剂， 反应 169.0h， 以to obtain 1.90 g (Yield based on ethyl 2-amino-3-phenylpropionate (racemic mixture)=40.0%) of ethyl (R)-2-amino-3-phenylpropionate hydrochloride as white crystals的产率得到D-苯丙氨酸乙酯盐酸盐
  参考文献：
  名称：

  PROCESS FOR PREPARING OPTICALLY ACTIVE (S OR R)-ALPHA-AMINO ACID AND OPTICALLY ACTIVE (R OR S)-ALPHA-AMINO ACID ESTER

  摘要：

  本发明揭示了一种制备光学活性（S或R）-α-氨基酸的方法，其表示为式（II）：其中R表示烷基，烯基，炔基，环烷基，芳基烷基，杂芳基烷基，芳基或杂芳基，每个基团都可以有取代基，而*表示不对称碳原子；以及光学活性（R或S）-α-氨基酸酯，其表示为式（III）：其中R1表示烷基，可以有取代基，而*表示不对称碳原子，前提是它的绝对构型与式（II）的化合物相反；所述方法包括在有机溶剂中，在脂肪酶或蛋白酶的存在下，选择性地将水与由式（I）表示的混合的α-氨基酸酯的对映体之一反应，其中R和R1的含义如上所定义。

  公开号：

  US20090042260A1

文献信息

• Antimicrobial toxicity studies of ionic liquids leading to a ‘hit’ MRSA selective antibacterial imidazolium salt
  作者：Deborah Coleman、Marcel Špulák、M. Teresa Garcia、Nicholas Gathergood

  DOI：10.1039/c2gc16090k

  日期：——

  Imidazolium salts can be classed as surfactants, detergents, ionic liquids, reagents, catalysts or solvents. A study of the toxicity and ecotoxicity of these salts yields valuable information for their use as pharmaceuticals as well as impact on the environment. Our approach to screen a series of chiral imidazolium salts for toxicity to bacteria and fungi, including clinical pathogen strains, has led to the identification of a ‘hit’ MRSA selective antimicrobial compound. Preliminary structure–activity-relationship (SAR) information (required position of L-phenylalanine and L-valine group) is also elucidated within this first generation of compounds. Conversely, most of the imidazolium salts were nontoxic (IC95 > 2 mM) to the 12 fungi strains and 8 bacteria strains screened, and we propose that they are suitable candidates for ‘green chemistry’ applications. Ecotoxicity studies (Biodegradation ISO 14593 ‘CO2 Headspace Test’) of two bromide ionic liquids containing L-phenylalanine residues indicate that these ionic liquids passed the test (>60% in 28 days) and classed as readily biodegradable.

  咪唑盐可分类为表面活性剂、洗涤剂、离子液体、试剂、催化剂或溶剂。对这些盐的毒性和生态毒性的研究，为其作为药物的使用以及对环境的影响提供了宝贵的信息。我们对一系列手性咪唑盐对细菌和真菌的毒性进行了筛选，包括临床病原菌株，从而鉴定出一种针对MRSA的选择性抗菌化合物。初步的结构-活性关系（SAR）信息（L-苯丙氨酸和L-缬氨酸集团所需的定位）也在这一代化合物中得以阐明。相反，大多数咪唑盐对筛选的12种真菌株和8种细菌株无毒（IC95 > 2 mM），我们提出它们是适合“绿色化学”应用的候选物质。生态毒性研究（ISO 14593生物降解“CO2顶空测试”）表明，含有L-苯丙氨酸残基的两种溴离子液体通过了测试（28天内>60%），被归类为易于生物降解。
• N-Heteroarylation of Optically Pure α-Amino Esters using the Pd-PEPPSI-IPent^Cl -<i>o</i> -picoline Pre-Catalyst
  作者：Sepideh Sharif、David Mitchell、Michael J. Rodriguez、Jennifer L. Farmer、Michael G. Organ

  DOI：10.1002/chem.201603933

  日期：2016.10.10

  and efficient method for the Pd‐catalyzed N‐heteroarylation of optically pure α‐amino esters was developed. Dichloro[1,3‐bis(2,6‐di‐3‐pentylphenyl)imidazol‐2‐ylidene](o‐picoline)palladium(II) (Pd‐PEPPSI‐IPentCl‐o‐picoline; PEPPSI=pyridine enhanced pre‐catalyst preparation, stabilization, and initiation) was shown to effectively couple a variety of amino acids as the tert‐butyl ester with heteroaryl chlorides

  开发了一种健壮，温和且有效的方法，用于Pd催化的光学纯α-氨基酯的N-杂芳基化反应。二氯[1,3-双（2,6-二-3-戊基苯基）咪唑-2-亚基]（ö甲基吡啶）合钯（II）（PD-PEPPSI-IPent氯- ö甲基吡啶; PEPPSI =吡啶增强预催化剂的制备，稳定化和引发）被证明可以高效地将叔丁酯与叔芳基氯化物等多种氨基酸有效地偶联，并且与酯相邻的酸性质子具有出色的立体保留能力。对照实验表明，消旋作用是碱介导的，使用Pd-PEPPSI-IPent Cl时没有消除Pd介导的β-氢化物的证据。，并且消旋化仅在产物形成后发生，即未芳基化的起始氨基酯在我们的反应条件下不会去质子化。研究还表明，增加氨基酸上酯部分的空间体积（例如，乙基至叔丁基）会大大减慢产品的外消旋作用。
• Borate esters as convenient reagents for direct amidation of carboxylic acids and transamidation of primary amides
  作者：Pavel Starkov、Tom D. Sheppard

  DOI：10.1039/c0ob01069c

  日期：——

  with a variety of carboxylic acids and amines. With trimethyl or tris(2,2,2-trifluoroethyl) borate, amides are obtained in good to excellent yield and high purity after a simple work-up procedure. Tris(2,2,2-trifluoroethyl) borate can also be used for the straightforward conversion of primary amides to secondary amidesvia transamidation.

  简单的硼酸盐可作为与各种羧酸和胺形成酰胺键的有效促进剂。与三甲基或三（2,2,2-三氟乙基）硼酸酯通过简单的后处理程序即可获得高至优异收率和高纯度的酰胺。 三（2,2,2-三氟乙基）硼酸酯也可用于通过酰胺交换将伯酰胺直接转化为仲酰胺。
• Specific inhibition of benzodiazepine receptor binding by some N-(indol-3-ylglyoxylyl) amino acid derivatives: stereoselective interactions
  作者：Giampaolo Primofiore、Anna M. Marini、Federico Da Settimo、Claudia Martini、Anna Bardellini、Gino Giannaccini、Antonio Lucacchini

  DOI：10.1021/jm00132a004

  日期：1989.12

  Several optically active N-(indol-3-ylglyoxylyl)amino acid derivatives were synthesized and tested for [3H]flunitrazepam displacing activity in bovine brain membranes. IC50 values were measured and revealed that the D form of the amino acid moiety of the compounds was more potent than both the L form and racemic form, suggesting a key role of the amino acid stereochemistry on the affinity to the benzodiazepine

  合成了几种旋光性的N-（吲哚-3-基乙二醛基）氨基酸衍生物，并测试了牛脑膜中[3H]氟硝西m的置换活性。测量IC 50值，发现化合物的氨基酸部分的D形式比L形式和外消旋形式都更有效，这表明氨基酸立体化学在与苯二氮卓受体的亲和力中起着关键作用。报告的最具活性的化合物的GABA比率和前惊厥药/惊厥药数据表明，它们在苯并二氮杂receptor受体上起反向激动剂的作用。
• Synthesis of malonamide pseudopeptidic compounds using a pseudo five-component reaction and evaluation of their gelation properties
  作者：Tahmineh Kenarkoohi、Abbas Rahmati

  DOI：10.1016/j.molliq.2018.12.029

  日期：2019.2

  five-component reaction. Amino acid esters, which were used in this reaction, were phenylalanine ethyl ester and glycine ethyl ester. MPPCS that were obtained from l-phenylalanine ethyl ester and glycine ethyl ester gave stable gels in the mixture of dimethyl sulfoxide (DMSO)/water as solvent while MPPCs derived from d-phenylalanine did not give gel. Also, when MPPCS of d- and l-form (1:1) were mixed, they

  通过基于异氰化物的假五组分反应制备了一类新的丙二酰胺假肽化合物（MPPC S）。用于该反应的氨基酸酯是苯丙氨酸乙酯和甘氨酸乙酯。由1-苯丙氨酸乙酯和甘氨酸乙酯得到的MPPC S在以二甲基亚砜（DMSO）/水为溶剂的混合物中得到稳定的凝胶，而衍生自d-苯丙氨酸的MPPC没有得到凝胶。此外，当MPPC小号的d -和升-形式（1：1）混合后，它们不能形成低浓度甚至高浓度的凝胶。凝胶的溶胶-凝胶相变温度表明它们具有令人满意的热稳定性。流变结果表明某些凝胶具有很高的机械强度。傅立叶变换红外（FT-IR）光谱表明，在这种自组装过程中，三种类型的驱动力具有关键作用，包括氢键，范德华力和π-π相互作用。此外，使用扫描电子显微镜（SEM）图像阐明了干凝胶的形态。