(S)-3-氨基-3-苯基丙酸盐酸盐 | 83649-47-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基酸盐
• 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-苯基丙酸盐酸盐
• 中文别名: L-(+)-3-氨基-3-苯基丙酸盐酸盐；S-3-氨基-3-苯基丙酸盐酸盐；L-3-氨基-3-苯基丙酸盐酸盐
• 英文名称: (S)-(+)-β-phenyl-β-alanine hydrochloride
• 英文别名: (S)-3-amino-3-phenylpropanoic acid hydrochloride；(S)-(-)-3-Amino-3-phenylpropionic acid hydrochloride；(3S)-3-amino-3-phenylpropanoic acid;hydrochloride
• CAS: 83649-47-2
• 化学式: C₉H₁₁NO₂*ClH
• 分子量: 201.653
• InChiKey: ABEBCTCOPRULFS-QRPNPIFTSA-N

物化性质

• 熔点：
  179-184 °C
• 溶解度：
  溶于甲醇、水
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 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：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	(S)-(+)-3-Amino-3-phenylpropionic acid hydrochloride Material Safety Data Sheet
Synonym:	None Known
CAS:	83649-47-2

Section 1 - Chemical Product MSDS Name:(S)-(+)-3-Amino-3-phenylpropionic acid hydrochloride Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
83649-47-2	(S)-(+)-3-Amino-3-phenylpropionic acid	ca. 100	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract. Inhalation may be fatal as a result of spasm, inflammation, edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. May cause burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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 water spray, dry chemical, carbon dioxide, or chemical foam.

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

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing.
Keep container tightly closed. Do not ingest or inhale. Use only in a chemical fume hood. Discard contaminated shoes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 83649-47-2: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 179 - 184 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H11NO2.HCl
Molecular Weight: 201.66

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 83649-47-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-(+)-3-Amino-3-phenylpropionic acid hydrochloride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, 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# 83649-47-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 83649-47-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 83649-47-2 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

制备方法与用途

用途：达泊西汀盐酸盐中间体

反应信息

• 作为反应物：
  描述：

  (S)-3-氨基-3-苯基丙酸盐酸盐 在 吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 反应 20.17h， 生成
  参考文献：
  名称：

  2'（3'）-OL-苯丙氨酰腺苷作为核糖体肽基转移酶的底物和抑制剂的类似物。

  摘要：

  2'（3'）-O-（L-3-氨基-3-苯基丙酰基）腺苷（2e），相应的D立体异构体2f，2'（3'）-O-（DL-苯基甘氨酰基）腺苷的化学合成描述了（2g），2'（3'）-O-（N-苄基甘氨酰基）腺苷（2h）和9（2-OL-苯丙氨酰基-β-D-木呋喃糖基）腺嘌呤（3b）。通过将5'-O-（4-甲氧基三苯甲基）腺苷与合适的N-苄氧基羰基或N-叔丁氧基羰基氨基酸与吡啶中的二环己基碳二亚胺酰化，获得化合物2e-h。N-（苄氧羰基）-D-苯基甘氨酸的相应反应导致氨酰基残基（化合物2c和2g）几乎完全消旋。随后的色谱分离和中间体2a-d的脱保护得到所需的目标衍生物2e-h。产物3b是通过类似的9-（3，将5-O-异亚丙基-β-D-呋喃呋喃糖基）腺嘌呤与N-（苄氧基羰基）-L-苯丙氨酸一起，然后脱保护。讨论了立体异构体2a和2b的2'和3'异构体的NMR光谱。化合物2g和3b都是大肠杆菌核糖体肽基转移

  DOI：

  10.1021/jm00356a010
• 作为产物：
  描述：

  左旋苯甘氨酸 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 氢气 、 silver benzoate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， -5.0~25.0 ℃ 、101.33 kPa 条件下， 反应 11.0h， 生成 (S)-3-氨基-3-苯基丙酸盐酸盐
  参考文献：
  名称：

  Crombie, Leslie; Haigh, David; Jones, Raymond C. F., Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 2047 - 2054

  摘要：

  DOI：

文献信息

• The use of β-lactams in the synthesis of spermine and spermidine alkaloids
  作者：Harry H. Wasserman、Gregory D. Berger

  DOI：10.1016/s0040-4020(01)92138-6

  日期：1983.1

  The optically active plant product homaline (6) has been synthesized in a convergent sequence starting with β-phenyl-β-alanine and putrescine (14) The key transformation in this sequence is the ring expansion by transamidation of a functionalized chiral β-lactam precursor

  旋光性植物产品荷马琳（6）已从β-苯基-β-丙氨酸和腐胺（14）开始，以收敛的顺序合成。该序列的关键转化是通过功能化的手性β-内酰胺前体的转酰胺作用进行的扩环
• Highly Diastereoselective and Enantioselective Preparation of Homoallylic Amines: Application for the Synthesis of β-Amino Acids and γ-Lactams
  作者：P. Veeraraghavan Ramachandran、Thomas E. Burghardt

  DOI：10.1002/chem.200401295

  日期：2005.7.18

  furnished homoallylic amines in good yields and high ee. A 11B NMR spectroscopy study revealed that the reactions do not proceed, even at room temperature, unless a molar equivalent of water or methanol is added. The first reagent-controlled asymmetric crotylboration and alkoxyallylboration of aldimines furnishing beta-methyl or beta-alkoxy homoallylic amines in very high diastereoselectivity and enantioselectivity

  在甲醇存在下，N-甲硅烷基和N-铝亚胺与B-烯丙基异硫代樟脑硼烷硼烷的反应，然后进行氧化后处理，以高收率和高ee提供了均烯丙基胺。11B NMR光谱研究表明，除非加入摩尔当量的水或甲醇，否则即使在室温下，反应也不会进行。本文报道了以非常高的非对映选择性和对映选择性提供β-甲基或β-烷氧基均烯丙基胺的醛亚胺的第一试剂控制的不对称巴豆基硼酸酯化和烷氧基烯丙基化。亚胺的巴豆基硼酸酯化和烷氧基烯丙基化仅与“烯丙基”-硼“酸酯”配合物一起进行，而不是与醛类一起使用“烯丙基”-二烷基硼试剂。这些反应也必须添加甲醇。已经描述了该方法在两个步骤中用于将代表性的腈转化为β-氨基酸的应用。另外，还报道了由腈制备手性δ-氨基醇和γ-内酰胺的方法。
• Enantioselective Synthesis of β‐Amino Acid Derivatives Enabled by Ligand‐Controlled Reversal of Hydrocupration Regiochemistry
  作者：Sheng Guo、Jiaqi Zhu、Stephen L. Buchwald

  DOI：10.1002/anie.202007005

  日期：2020.11.16

  A Cu‐catalyzed enantioselective hydroamination of α,β‐unsaturated carbonyl compounds for the synthesis of β‐amino acid derivatives was achieved through ligand‐controlled reversal of the hydrocupration regioselectivity. While the hydrocupration of α,β‐unsaturated carbonyl compounds to form α‐cuprated species has been extensively investigated, we report herein that, in the presence of an appropriate

  铜催化的α,β-不饱和羰基化合物的对映选择性加氢胺化反应合成β-氨基酸衍生物是通过配体控制的氢铜反应区域选择性逆转实现的。虽然已经广泛研究了 α,β-不饱和羰基化合物的氢铜反应形成 α-铜酸盐物质，但我们在本文中报告说，在适当的辅助手性配体存在下，肉桂酸衍生物可以观察到相反的区域化学，导致将铜传递到 β 位。这种铜可以与亲电子胺化试剂 1,2-苯并异恶唑反应，提供富含对映体的 β-氨基酸衍生物，这是合成天然产物和生物活性小分子的重要组成部分。
• Highly Enantioselective Synthesis of N-Protected β-Amino Malonates Catalyzed by Magnetically Separable Heterogeneous Rosin-Derived Amino Thiourea Catalysts: A Stereocontrolled Approach to β-Amino Acids
  作者：Hao Zhu、Xianxing Jiang、Xinghua Li、Chen Hou、Yu Jiang、Ke Hou、Rui Wang、Yanfeng Li

  DOI：10.1002/cctc.201300089

  日期：2013.8

  A rosin by any other name: Magnetic‐nanoparticle‐supported bifunctional rosin‐derived tertiary amino thiourea catalysts are developed for the stereocontrolled synthesis of chiral β‐amino acids. Boc=tert‐butoxycarbonyl, Bn=benzyl.

  任意其他名称的松香：磁性纳米粒子负载的双官能松香衍生的叔氨基硫脲催化剂可用于立体控制手性β-氨基酸的合成。Boc =叔丁氧羰基，Bn =苄基。
• Tropane derivatives useful in therapy
  申请人：——

  公开号：US20020013337A1

  公开（公告）日：2002-01-31

  The present invention provides compounds of the formula: 1 wherein R 1 is C 3-6 cycloalkyl optionally substituted by one or more fluorine atoms, or C 1-6 alkyl optionally substituted by one or more fluorine atoms, or C 3-6 cycloalkylmethyl optionally ring-substituted by one or more fluorine atoms; and R 2 is phenyl optionally substituted by one or more fluorine atoms, to pharmaceutically acceptable salts and solvates thereof, and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such compounds.

  本发明提供了以下结构的化合物：其中R1是C3-6环烷基，可选择地被一个或多个氟原子取代，或者是C1-6烷基，可选择地被一个或多个氟原子取代，或者是C3-6环烷基甲基，可选择地被一个或多个氟原子取代；以及R2是苯基，可选择地被一个或多个氟原子取代，其药学上可接受的盐和溶剂合物，以及用于制备、用于制备的中间体、含有这些化合物的组合物和用途的制备过程。