Boc-L-4-溴苯丙氨酸 | 62129-39-9

• 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: Boc-L-4-溴苯丙氨酸
• 中文别名: (S)-N-BOC-4-溴苯丙氨酸；叔丁氧羰基-4-溴-L-苯丙氨酸；(S)-N-Boc-4-溴苯丙氨酸；Boc-4-溴-L-苯丙氨酸
• 英文名称: 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine
• 英文别名: (S)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid；(2S)-3-(4-bromophenyl)-2-(tert-butoxycarbonylamino)propanoic acid；N-Boc-4-bromo-L-phenylalanine；4-bromo-N-(tert-butoxycarbonyl)-L-phenylalanine；(s)-n-Boc-4-bromophenylalanine；(2S)-3-(4-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 62129-39-9
• 化学式: C₁₄H₁₈BrNO₄
• 分子量: 344.205
• InChiKey: ULNOXUAEIPUJMK-NSHDSACASA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  475.3±40.0 °C(Predicted)
• 密度：
  1.5311 (rough estimate)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 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)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2924299090
• 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)-N-BOC-4-Bromophenylalanine, 95%, (98% E.E.) Material Safety Data Sheet
Synonym:	N-tert-Butoxycarbonyl-4-Bromophenyl-L-Alanine.
CAS:	62129-39-9

Section 1 - Chemical Product MSDS Name: (S)-N-BOC-4-Bromophenylalanine, 95%, (98% E.E.) Material Safety Data Sheet
Synonym: N-tert-Butoxycarbonyl-4-Bromophenyl-L-Alanine.

---

SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
62129-39-9	(S)-N-BOC-4-Bromophenylalanine	95%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW The toxicological properties of this material have not been fully investigated. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

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. Wash mouth out with 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.

---

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.

---

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.

---

SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. 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.

---

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# 62129-39-9: 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.

---

SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Solid
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 118 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: C14H18BrNO4
Molecular Weight: 344.2

---

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.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

---

SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 62129-39-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-BOC-4-Bromophenylalanine - Not listed by ACGIH, IARC, or NTP.

---

SECTION 12 - ECOLOGICAL INFORMATION

---

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

---

SECTION 14 - TRANSPORT INFORMATION IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR Not regulated as a hazardous material.

---

SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 62129-39-9: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 62129-39-9 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 62129-39-9 is not listed on the TSCA inventory. It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 1/16/2002 Revision #2 Date: 10/05/2004 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Boc-Phe(4-Br)-OH是一种苯丙氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  Boc-L-4-溴苯丙氨酸 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 dipotassium hydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 碳酸氢钠 、 一水合肼 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 甲基叔丁基醚 、 水 、 乙腈 为溶剂， 反应 30.0h， 生成 3-氯-n-((s)-1-(2-(二甲基氨基)乙酰氨基)-3-(4-(8-((s)-1-羟基乙基)咪唑并[1,2-a]吡啶-2-基)苯基)丙烷-2-基)-4-异丙氧基苯甲酰胺
  参考文献：
  名称：

  发现和开发新型CENP-E抑制剂GSK923295A的高效，可扩展且鲁棒的路线

  摘要：

  CENP-E抑制剂3-chloro- N -{（1 S）-2-[（N，N-二甲基甘氨酰）氨基] -1-[（4- {8- [描述了（1S）-1-羟乙基]咪唑并[1,2 - a ]吡啶-2-基}苯基）甲基]乙基} -4-[[1-甲基乙基）氧基]苯甲酰胺（GSK923295A）。通往GSK923295A的现有途径昂贵，不稳固，使用过的非理想试剂，并且始终难以提供临床研究所需的API。新的综合从容易获得的l开始-苯丙氨醇，使用关键的Friedel-Crafts酰化反应以及选择性的酰化化学反应平稳地转化为GSK923295A。GSK923295A的下游化学反应产量高且稳定，并且首先在千克规模上证明了所产生的过程，随后在成功制备了55千克的中试工厂中进行了证明。生成的过程简单，使用较便宜的原料，更绿色，因为它避免了使用铝，锡和溴化化学试剂，并且无需进行色谱纯化。还讨论了路线衍生的杂质，如何明确地准备它

  DOI：

  10.1021/op100186c
• 作为产物：
  描述：

  对溴肉桂酸 在 ammonium hydroxide 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.33h， 生成 Boc-L-4-溴苯丙氨酸
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Optically Purel- andd-Biarylalanines through Biocatalytic Asymmetric Amination and Palladium-Catalyzed Arylation

  摘要：

  A chemoenzymatic approach was developed and optimized for the synthesis of a range of N-protected nonnatural L- and D-biarylalanine derivatives. Starting from 4-bromocinnamic acid and 4-bromophenylpyruvic acid using a phenylalanine ammonia lyase (PAL) and an evolved D-amino acid dehydrogenase (DAADH), respectively, both enantiomers of 4-bromophenylalanine were obtained and subsequently coupled with a panel of arylboronic acids to give the target compounds in high yield and optical purity under mild aqueous conditions.

  DOI：

  10.1021/acscatal.5b01132

文献信息

• [EN] PERFLUORO-TERT-BUTYL HYDROXYPROLINE<br/>[FR] PERFLUORO-TERT-BUTYLE HYDROXYPROLINE
  申请人：ZONDLO NEAL

  公开号：WO2014127052A1

  公开（公告）日：2014-08-21

  The present invention provides novel analogues of alpha amino acids, comprising a perfluoro-tert-butyl group, and molecules comprising the novel analogues. Also provided are a wide range of applications of the novel analogues in therapeutics, theranostics and pharmaceuticals as well as in imaging applications. In particular, the use of the novel analogues in detecting or modifying a target molecule is provided.

  本发明提供了新型α氨基酸的类似物，包括全氟叔丁基基团，以及包含这些新型类似物的分子。还提供了这些新型类似物在治疗学、治疗诊断学、制药学以及成像应用中的广泛应用。特别提供了在检测或修改靶分子中使用这些新型类似物的方法。
• Interaction of Papain-like Cysteine Proteases with Dipeptide-Derived Nitriles
  作者：Reik Löser、Klaus Schilling、Elke Dimmig、Michael Gütschow

  DOI：10.1021/jm050686b

  日期：2005.12.1

  were introduced, and systematic fluorine, bromine, and phenyl scans for phenylalanine in the P2 position were performed. Moreover, the N-terminal protection was varied. Kinetic investigations were carried out with cathepsin L, S, and K as well as papain. Changes in the backbone structure of the parent N-(tert-butoxycarbonyl)-phenylalanyl-glycine-nitrile (16), such as the introduction of an R-configured

  制备一系列44个在P2位具有各种氨基酸和在P1位具有甘氨酸的二肽腈，并将其评估为半胱氨酸蛋白酶的抑制剂。关于P2-S2相互作用对酶抑制剂复合物形成的重要贡献，重点是将结构多样性引入P2侧链。引入了非蛋白氨基酸，并进行了系统的氟，溴和苯基扫描，以检测P2位置的苯丙氨酸。而且，N-末端保护是多种多样的。使用组织蛋白酶L，S和K以及木瓜蛋白酶进行动力学研究。母体N-（叔丁氧羰基）-苯丙氨酰基-甘氨酸-腈的骨架结构变化（16），例如将R构型的氨基酸或氮杂氨基酸引入P2以及P1氮的甲基化，会导致亲和力的急剧下降。示例性地，16的氰基被醛或甲基酮官能团取代。关于靶酶的底物特异性，讨论了构效关系。
• Design, synthesis and stepwise optimization of nitrile-based inhibitors of cathepsins B and L
  作者：Lorenzo Cianni、Fernanda Dos Reis Rocho、Vinícius Bonatto、Felipe Cardoso Prado Martins、Jerônimo Lameira、Andrei Leitão、Carlos A. Montanari、Anwar Shamim

  DOI：10.1016/j.bmc.2020.115827

  日期：2021.1

  Human cathepsin B (CatB) is an important biological target in cancer therapy. In this work, we performed a knowledge-based design approach and the synthesis of a new set of 19 peptide-like nitrile-based cathepsin inhibitors. Reported compounds were assayed against a panel of human cysteine proteases: CatB, CatL, CatK, and CatS. Three compounds (7h, 7i, and 7j) displayed nanomolar inhibition of CatB

  人组织蛋白酶 B (CatB) 是癌症治疗中的重要生物学靶点。在这项工作中，我们采用了一种基于知识的设计方法，并合成了一组新的 19 种肽样腈基组织蛋白酶抑制剂。针对一组人半胱氨酸蛋白酶对报告的化合物进行了分析：CatB、CatL、CatK 和 CatS。三种化合物（7h、7i和7j）显示出对 CatB 的纳摩尔抑制以及对 CatK 和 CatL 的选择性。的选择性通过使用的组合来实现对位联苯环在P 3，卤代苯丙氨酸P 2和Thr-O-BZ组在P 1。同样地，化合物7I和7J在所研究的酶组中显示出选择性 CatB 抑制作用。我们还描述了一个成功的例子，用生物等排置换磺酰胺 [ 7e  →  6b ]的酰胺键，我们观察到 CatB 的亲和力和选择性增加，同时降低了化合物的亲脂性 (ilogP)。我们基于知识的设计方法和各自的结构-活性关系为治疗相关组织蛋白酶的特定配体-靶标相互作用提供了见解。
• Prodrugs of GABA analogs, compositions and uses thereof
  申请人：Gallop A. Mark

  公开号：US20060229361A1

  公开（公告）日：2006-10-12

  The present invention provides prodrugs of GABA analogs, pharmaceutical compositions of prodrugs of GABA analogs and methods for making prodrugs of GABA analogs. The present invention also provides methods for using prodrugs of GABA analogs and methods for using pharmaceutical compositions of prodrugs of GABA analogs for treating or preventing common diseases and/or disorders.

  本发明提供了GABA类似物的前药，GABA类似物前药的药物组合物以及制备GABA类似物前药的方法。本发明还提供了使用GABA类似物前药的方法以及使用GABA类似物前药的药物组合物治疗或预防常见疾病和/或疾病的方法。
• A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water
  作者：Arnaud Peramo、Ibrahim Abdellah、Shannon Pecnard、Julie Mougin、Cyril Martini、Patrick Couvreur、Vincent Huc、Didier Desmaële

  DOI：10.3390/molecules25061459

  日期：——

  (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 4′-arylated

  发现用N-杂环卡宾（NHC）-钯配合物功能化的纳米杯[8]芳烃是水溶性碘代和溴代芳基化合物与环状三醇芳基硼酸酯在低温下进行Suzuki-Miyaura交叉偶联反应的有效纳米反应器。水，不含任何有机助溶剂。结合改进的从硼酸一步合成三醇芳基硼酸酯的方法，这一非常高效的新工具以低催化剂负载量和广泛的官能团耐受性，以良好的产率提供了多种 4'-芳基化苯丙氨酸和酪氨酸。