乙酰基-4-溴-DL-苯基丙氨酸 | 273730-59-9

• 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: 乙酰基-4-溴-DL-苯基丙氨酸
• 英文名称: N-acetyl-4-bromophenylalanine
• 英文别名: 2-(acetylamino)-3-(4-bromophenyl)propanoic acid；AC-P-Bromo-DL-phe-OH；2-acetamido-3-(4-bromophenyl)propanoic acid
• CAS: 273730-59-9
• 化学式: C₁₁H₁₂BrNO₃
• 分子量: 286.125
• InChiKey: LDCUXIARELPUCD-UHFFFAOYSA-N

物化性质

• 沸点：
  507.4±45.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-p-bromo-dl-phe-oh
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: Ac-p-bromo-dl-phe-oh
CAS number: 273730-59-9

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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: C11H12BrNO3
Molecular weight: 286.1

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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 bromide.

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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：

  乙酰基-4-溴-DL-苯基丙氨酸 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以68.4%的产率得到L-4-溴苯丙氨酸
  参考文献：
  名称：

  Asymmetric Synthesis of Unnatural Amino Acids and Tamsulosin Chiral Intermediate

  摘要：

  An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2012.748075
• 作为产物：
  描述：

  ethyl-3-(4-bromophenyl)-2-(hydroxyimino)propanoate 在 Raney nickel 作用下， 以 甲醇 为溶剂， 生成 乙酰基-4-溴-DL-苯基丙氨酸
  参考文献：
  名称：

  使用硼氢化钠-雷尼镍系统还原肟、亚胺和腙中 CN 双键的简便方法

  摘要：

  摘要 开发了一种在 Raney Ni 催化下用硼氢化钠还原肟、亚胺和腙中 CN 双键的实用方法。反应在碱性水溶液中进行，经过简单的程序，以中等收率得到所需产物。该方法可用于合成更简单的脂肪族或芳香族胺及其类似物。图形概要

  DOI：

  10.1080/00397911.2011.562063

文献信息

• Real-time monitoring of tritium gas reactions using Raman spectroscopy
  作者：J. Richard Heys、Mark E. Powell、Don E. Pivonka

  DOI：10.1002/jlcr.887

  日期：2004.11

  The utility of Raman spectroscopy for noninvasive, real-time monitoring of a range of tritium gas labeling reactions has been investigated, using deuterium gas as a model in most cases. Reaction types include organoiridium-catalyzed heteroatom-directed exchange (HDE), olefin hydrogenation and catalytic aryl dehalogenation. Five examples of HDE reactions with several different substrate types were monitored by observation of Raman vibrational bands sensitive to the isotopic substitutions. Changes in peak intensities and/or frequencies associated with the course of labeling are clearly observable at concentrations and reaction scales typical of tritium gas reactions. Similarly, Raman bands sensitive to the chemical changes that occur during catalytic deuterogenation of an olefin and to catalytic deuterium–bromine exchange of an aryl bromide were successfully monitored. This methodology can provide unprecedented real-time information, otherwise difficult to obtain, over the course of such reactions. Copyright © 2004 John Wiley & Sons, Ltd.

  通过在大多数情况下以氘气作为模型，研究了拉曼光谱在非侵入性、实时监测一系列氚气标记反应中的应用。反应类型包括有机铱催化的杂原子导向交换（HDE）、烯烃加氢和催化芳基脱卤。通过观察对同位素取代敏感的拉曼振动谱带，监测了五种不同底物类型的HDE反应。在典型的氚气反应浓度和反应规模下，可以清晰地观察到与标记过程相关的峰强度和/或频率的变化。同样，成功监测了对烯烃催化氘化过程中化学变化敏感的拉曼谱带，以及对芳基溴化物催化氘-溴交换过程中化学变化敏感的拉曼谱带。这种方法能够在这些反应过程中提供前所未有的实时信息，否则这些信息是难以获得的。版权所有 © 2004 John Wiley & Sons, Ltd。
• [EN] pH-SENSITIVE PEPTIDES<br/>[FR] PEPTIDES SENSIBLES AU PH
  申请人：RHODE ISLAND COUNCIL ON POSTSECONDARY EDUCATION

  公开号：WO2017165452A1

  公开（公告）日：2017-09-28

  The present subject matter provides pH triggered peptides, as well as compositions methods, devices, and systems comprising the same. The pH triggered peptides include cyclic and short linear peptides, and may have higher affinity to a membrane lipid bilayer at low pH than at neutral or high pH.

  本主题提供了pH触发的肽以及包含它们的组合物、方法、装置和系统。pH触发的肽包括环状和短线性肽，可能在低pH下与膜脂双层具有比中性或高pH下更高的亲和力。
• Substituted imidazoles as bombesin receptor subtype-3 modulators
  申请人：Chen David

  公开号：US20100004280A1

  公开（公告）日：2010-01-07

  Certain novel substituted imidazoles are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.

  某些新型取代咪唑是人类炸弹素受体的配体，特别是人类炸弹素受体亚型-3（BRS-3）的选择性配体。它们因此可用于治疗、控制或预防对BRS-3调节敏感的疾病和障碍，例如肥胖症和糖尿病。
• SUBSTITUTED IMIDAZOLES AS BOMBESIN RECEPTOR SUBTYPE-3 MODULATORS
  申请人：Chen David

  公开号：US20120088788A1

  公开（公告）日：2012-04-12

  Certain novel substituted imidazoles are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.

  某些新型取代咪唑是人类炸弹素受体的配体，特别是人类炸弹素受体亚型3（BRS-3）的选择性配体。因此，它们可用于治疗、控制或预防对BRS-3调节敏感的疾病和障碍，例如肥胖症和糖尿病。
• Biological Screening and Crystallographic Studies of Hydroxy γ-Lactone Derivatives to Investigate PPARγ Phosphorylation Inhibition
  作者：Davide Capelli、Giulia Cazzaniga、Matteo Mori、Antonio Laghezza、Fulvio Loiodice、Martina Quaglia、Elisa Negro、Fiorella Meneghetti、Stefania Villa、Roberta Montanari

  DOI：10.3390/biom13040694

  日期：——

  PPARγ represents a key target for the treatment of type 2 diabetes and metabolic syndrome. To avoid serious adverse effects related to the PPARγ agonism profile of traditional antidiabetic drugs, a new opportunity is represented by the development of molecules acting as inhibitors of PPARγ phosphorylation by the cyclin-dependent kinase 5 (CDK5). Their mechanism of action is mediated by the stabilization

  PPARγ 是治疗 2 型糖尿病和代谢综合征的关键靶标。为了避免与传统抗糖尿病药物的 PPARγ 激动作用相关的严重不良反应，开发作为细胞周期蛋白依赖性激酶 5 (CDK5) 的 PPARγ 磷酸化抑制剂的分子代表了一个新的机会。它们的作用机制是通过稳定含有 Ser273（PPARγ 同种型 1 命名法中的 Ser245）的 PPARγ β-折叠介导的。在本文中，我们报告了从内部图书馆的筛选中鉴定出新的基于 γ-羟基-内酯的 PPARγ 结合剂。这些化合物对 PPARγ 表现出非激动剂特性，其中一种通过主要作用于 PPARγ 稳定作用并发挥弱 CDK5 抑制作用来防止 Ser245 PPARγ 磷酸化。