(S)-3-氨基-3-(2-氟苯基)-丙酸 | 151911-32-9

• 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-(2-氟苯基)-丙酸
• 英文名称: (S)-3-amino-3-(2'-fluorophenyl)propanoic acid
• 英文别名: (S)-3-amino-3-(2-fluorophenyl)propionic acid；(S)-3-amino-3-(2-fluoro-phenyl)-propionic acid；(3S)-3-azaniumyl-3-(2-fluorophenyl)propanoate
• CAS: 151911-32-9
• 化学式: C₉H₁₀FNO₂
• mdl: MFCD00193241
• 分子量: 183.182
• InChiKey: RSCLTSJQAQBNCE-QMMMGPOBSA-N

物化性质

• 沸点：
  302.6±32.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922499990

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
(S)-3-Amino-3-(2-fluoro-phenyl)-propionic acid
Product Name:
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
(S)-3-Amino-3-(2-fluoro-phenyl)-propionic acid
Ingredient name:
CAS number: 151911-32-9

---

Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

---

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.

---

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.

---

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.
Storage: Store in closed vessels.

---

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.

---

Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H10FNO2
Molecular weight: 183.2

---

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 fluoride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-3-氨基-3-(2-氟苯基)-丙酸 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.67h， 生成 (S)-3-[5-(3-bromophenyl)-5,6,6-trimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino]-3-(2-fluorophenyl)propan-1-ol
  参考文献：
  名称：

  NOVEL SUBSTITUTED PHENYL-OXATHIAZINE DERIVATIVES, METHOD FOR PRODUCING THEM, DRUGS CONTAINING SAID COMPOUNDS AND THE USE THEREOF

  摘要：

  该发明涉及公式（I）的化合物及其生理上可接受的盐。所述化合物适用于治疗高血糖等症状。

  公开号：

  US20130338066A1
• 作为产物：
  描述：

  tert-butyl (S)-3-amino-3-(2'-fluorophenyl)propanoate 在 盐酸 、 水 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以96%的产率得到(S)-3-氨基-3-(2-氟苯基)-丙酸
  参考文献：
  名称：

  Asymmetric synthesis of β-fluoroaryl-β-amino acids

  摘要：

  The conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of beta-fluoroaryl-alpha,beta-unsaturated esters gave the corresponding beta-amino esters with high diastereoselectivity and in good isolated yields. Sequential treatment of the resultant beta-fluoroaryl-beta-amino esters under optimised hydrogenolysis conditions, followed by ester hydrolysis with 2.0 M aq HCl, provided access to a range of beta-fluoroaryl-beta-amino acids in good yield. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.001

文献信息

• [EN] 4 -HYDROXY- ISOQUINOLINE COMPOUNDS AS HIF HYDROXYLASE INHIBITORS<br/>[FR] COMPOSÉS 4-HYDROXY-ISOQUINOLÉINE COMME INHIBITEURS D'HYDROXYLASE HIF
  申请人：FIBROGEN INC

  公开号：WO2013134660A1

  公开（公告）日：2013-09-12

  The present invention relates to novel compounds of formula (I), and compositions capable of inhibiting PHD1 enzyme activity selectively over other isoforms, for example, PHD2 and/or PHD3 enzymes. The invention also relates to compounds of formula (I) for use in disorders such as muscle degeneration, colitis, IBD, and certain ischemias.

  本发明涉及式(I)的新化合物，以及能够选择性地抑制PHD1酶活性而不影响其他同工酶（例如PHD2和/或PHD3酶）的组合物。该发明还涉及式(I)的化合物在肌肉退化、结肠炎、炎症性肠病和某些缺血症等疾病中的应用。
• Influence of the aromatic moiety in α- and β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from Pantoea agglomerans
  作者：Andrea Varga、Gergely Bánóczi、Botond Nagy、László Csaba Bencze、Monica Ioana Toşa、Ákos Gellért、Florin Dan Irimie、János Rétey、László Poppe、Csaba Paizs

  DOI：10.1039/c6ra02964g

  日期：——

  isomerization of various racemic α- and β-arylalanines catalysed by phenylalanine 2,3-aminomutase from Pantoea agglomerans (PaPAM) was investigated. Both α- and β-arylalanines were accepted as substrates when the aryl moiety was relatively small, like phenyl, 2-, 3-, 4-fluorophenyl or thiophen-2-yl. While 2-substituted α-phenylalanines bearing bulky electron withdrawing substituents did not react, the corresponding

  在这项研究中，Pantoea agloglomerans的苯丙氨酸2，3-氨基变位酶催化的各种外消旋α-和β-芳基丙氨酸的对映异构体选择性异构化（PaPAM）进行了调查。当芳基部分相对较小时，如苯基，2-，3-，4-氟苯基或噻吩-2-基，α-和β-芳基丙氨酸均被接受为底物。尽管带有大量吸电子取代基的2-取代的α-苯丙氨酸没有反应，但相应的取代的β-芳基类似物却被迅速转化。3-和4-取代的α-芳基丙氨酸的转化顺利进行，而相应的β-芳基丙氨酸的转化不良或不存在。在pH 7-9范围内，对外消旋α-或β-（噻吩-2-基）丙氨酸的转化率没有明显影响，而氨的浓度（碳酸铵从50 mM增加到1000 mM）则抑制了异构化逐步减少副产物的量（即（E检测到）-3-（噻吩-2-基）丙烯酸。在所有情况下，产物的高ee值表明优异的对映异构体选择性和异构化的立体特异性，除了来自β-异构体的（S）-2-硝基-α-苯丙氨酸（ee
• The Bacterial Ammonia Lyase EncP: A Tunable Biocatalyst for the Synthesis of Unnatural Amino Acids
  作者：Nicholas J. Weise、Fabio Parmeggiani、Syed T. Ahmed、Nicholas J. Turner

  DOI：10.1021/jacs.5b07326

  日期：2015.10.14

  deracemization cascades (giving (S)- or (R)-α-phenylalanine derivatives, respectively), and also eukaryotic phenylalanine aminomutases (PAMs) for the synthesis of the (R)-β-products. Herein, we present the investigation of another family member, EncP from Streptomyces maritimus, thereby expanding the biocatalytic toolbox and enabling the production of the missing (S)-β-isomer. EncP was found to convert

  I类裂解酶家族的酶催化氨向丙烯酸芳基酯的不对称加成，产生作为产物的高价值氨基酸。最近的例子包括使用苯丙氨酸氨裂解酶 (PAL)，单独使用或作为去消旋级联的途径（分别提供 (S)- 或 (R)-α-苯丙氨酸衍生物），以及真核苯丙氨酸氨基变位酶 (PAM) (R)-β-产物的合成。在此，我们介绍了对来自 Streptomyces maritimus 的另一个家族成员 EncP 的研究，从而扩展了生物催化工具箱并能够生产缺失的 (S)-β-异构体。发现 EncP 将一系列芳基丙烯酸酯转化为 (S)-α- 和 (S)-β-芳基丙氨酸的混合物，其区域选择性与每个底物环上的吸电子/供电子基团的强度相关。野生型酶的低区域选择性通过基于结构的合理设计得到解决，以产生三种对α-或β-产物具有改变偏好的变体。通过检查各种生物催化剂/底物组合，证明可以调整反应的胺化模式，以根据需要实现 99:1 和 1:99 之间的
• Stereoselective Chemoenzymatic Preparation of β-Amino Esters: Molecular Modelling Considerations in Lipase-Mediated Processes and Application to the Synthesis of (<i>S</i>)-Dapoxetine
  作者：María Rodríguez-Mata、Eduardo García-Urdiales、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1002/adsc.200900676

  日期：2010.2.15

  the kinetic resolution of the corresponding β-amino esters. Although the enzymatic acylations of the amino group with ethyl methoxyacetate showed synthetically useful enantioselectivities, the hydrolyses of the ester group catalyzed by lipase from Pseudomonas cepacia have been identified as the optimal processes concerning both activity and enantioselectivity. The enantiopreference of this lipase in these

  已经通过立体选择性化学酶法制备了多种旋光的3-氨基-3-芳基丙酸衍生物。关键步骤是相应的β-氨基酯的动力学拆分。尽管氨基用甲氧基乙酸乙酯的酶促酰化显示了合成上有用的对映选择性，但是已经鉴定出由洋葱假单胞菌的脂肪酶催化的酯基的水解是关于活性和对映选择性的最佳方法。在分子水平上，已通过使用基于片段的方法解释了这些脂​​肪酶在这些反应中的对映体优先性，其中最有利的苯环结合位点和最稳定的3-氨基丙酸酯核心构象与（小号）-主要产品的配置。为了理解苯环中存在的不同取代模式的影响，已经比较了酶促反应的转化率和对映选择性值。该化学酶途径已成功地用于制备（S）-达泊西汀合成中的有价值的中间体，该中间体已经以优异的光学纯度化学合成。
• [EN] SUBSTITUTED 3-HETEROAROYLAMINO-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS<br/>[FR] DÉRIVÉS SUBSTITUÉS DE L'ACIDE 3-HÉTÉROAROYLAMINO-PROPIONIQUE ET LEUR UTILISATION COMME COMPOSÉS PHARMACEUTIQUES
  申请人：SANOFI SA

  公开号：WO2012101197A1

  公开（公告）日：2012-08-02

  The present invention relates to compounds of the formula (I), wherein A, D, E, L, G, R10, R30, R40, R50 and R60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

  本发明涉及式(I)的化合物，其中A、D、E、L、G、R10、R30、R40、R50和R60具有所述权利要求中指示的含义，它们是有价值的药物活性化合物。它们是蛋白酶卡特普西A的抑制剂，可用于治疗动脉硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。本发明还涉及式(I)化合物的制备方法、它们的用途以及包含它们的药物组合物。