BOC-Β-丙氨酸-对硝基苯酯 | 17547-09-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: BOC-Β-丙氨酸-对硝基苯酯
• 中文别名: N-叔丁氧羰基-BETA-丙氨酸4-硝基苯酯；4-硝基-3-((叔丁氧基羰基)氨基)丙酸苯酯
• 英文名称: 4-nitrophenyl 3-((tertbutoxycarbonyl)amino)propanoate
• 英文别名: 4-nitrophenyl tBoc-β-alanine ester；4-nitrophenyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]propionate；Boc-beta-alanine 4-nitrophenyl ester；(4-nitrophenyl) 3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 17547-09-0
• 化学式: C₁₄H₁₈N₂O₆
• mdl: MFCD00057613
• 分子量: 310.307
• InChiKey: NQNGYJVVBTUENI-UHFFFAOYSA-N

物化性质

• 沸点：
  473.0±30.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-beta-alanine 4-nitrophenyl ester
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: Boc-beta-alanine 4-nitrophenyl ester
CAS number: 17547-09-0

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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, refrigerated.
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: C14H18N2O6
Molecular weight: 310.3

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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.

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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：

  BOC-Β-丙氨酸-对硝基苯酯 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 [4-[Bis(phenylmethoxycarbonylamino)methylideneamino]phenyl] 3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  以对胍基苯基和对（胍基甲基）苯基酯为酰基供体的酶促肽合成。

  摘要：

  制备了两个系列的“反向底物”，N-Boc-氨基酸对-胍基苯基酯和对-（胍基甲基）苯基酯，作为用于酶促肽合成的酰基供体组分。分析了这些酯对牛和灰链霉菌（SG）胰蛋白酶的动力学行为。基于底物的空间特征，讨论了这些酶的活性位点对催化效率的空间需求。发现这些底物容易与氨基酸对硝基苯胺偶联以产生肽。SG胰蛋白酶是所测试的酶（牛，猪和SG胰蛋白酶）中最有效的催化剂。

  DOI：

  10.1248/cpb.46.846
• 作为产物：
  描述：

  对硝基苯酚 、 Boc-beta-丙氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 BOC-Β-丙氨酸-对硝基苯酯
  参考文献：
  名称：

  以对胍基苯基和对（胍基甲基）苯基酯为酰基供体的酶促肽合成。

  摘要：

  制备了两个系列的“反向底物”，N-Boc-氨基酸对-胍基苯基酯和对-（胍基甲基）苯基酯，作为用于酶促肽合成的酰基供体组分。分析了这些酯对牛和灰链霉菌（SG）胰蛋白酶的动力学行为。基于底物的空间特征，讨论了这些酶的活性位点对催化效率的空间需求。发现这些底物容易与氨基酸对硝基苯胺偶联以产生肽。SG胰蛋白酶是所测试的酶（牛，猪和SG胰蛋白酶）中最有效的催化剂。

  DOI：

  10.1248/cpb.46.846

文献信息

• Host-guest complexation. 31. A transacylase partial mimic
  作者：Donald J. Cram、Howard Edan Katz、Ira B. Dicker

  DOI：10.1021/ja00329a059

  日期：1984.8

  Les hotes sont des macrocycles a 20 chainons et sont composes en reliant l'une a l'autre des unites: aryloxy, uree cyclique, pyridyle, biphenyle, ethylene, methylene et oxygene. Etude cinetique de l'acylation des hotes hydroxymethyles par les invites esters p-nitrophenyles d'aminoacides

  Les hotes sont des macrocycles a 20 chainons et sont 组成依赖 l'une a l'autre des unites: aryloxy, uree cyclique, pyridyle, biphenyle, ethylene, methylene etoxye。Etude cinetique de l'acylation des hotes hydroxymethyles par les 邀请酯类对硝基苯类 d'aminoacides
• Substituted indolizino\x9b1,2-b!quinolinones
  申请人：SmithKline Beecham Corporation

  公开号：US05883255A1

  公开（公告）日：1999-03-16

  The present invention provides a method of treating viral infections by using antiviral substituted indolizino\x9b1,2-b!quinolinone compounds, antiviral substituted indolizino\x9b1,2-b!quinolinone compounds, and pharmaceutical compositions thereof.

  本发明提供了一种使用抗病毒取代的吲哚嗪并[1,2-b]喹啉酮化合物、抗病毒取代的吲哚嗪并[1,2-b]喹啉酮化合物以及其制成的药物组合物治疗病毒感染的方法。
• Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C–H Activation: Synthesis of Pyrazolo[1,5-<i>a</i>]pyrimidines
  作者：Gia L. Hoang、Andrew D. Streit、Jonathan A. Ellman

  DOI：10.1021/acs.joc.8b02606

  日期：2018.12.21

  pyrimidine ring by employing ethyl glyoxylate and trimethyl orthoformate in place of the aldehyde, respectively. In addition, a range of sulfoxonium ylides provided products in good yields to establish that aryl, heteroaryl, and branched and unbranched alkyl substituents can be introduced with this reagent. Finally, the first use of a formyl sulfoxonium ylide in a chemical transformation enabled the

  公开了一种有效的三组分策略，用于Rh（III）催化的现成的3-氨基吡唑，醛和亚砜基鎓盐的环化反应，从而得到各种吡唑并[1,5-a]嘧啶。反应在简单的台式条件下使用短时间的微波加热进行。对于许多取代的氨基吡唑以及非常多种的芳香族和杂芳香族醛，包括那些结合了吸电子，给电子，碱性氮，卤化物和酸性官能团的醛，均获得了良好的收率。通过分别使用乙醛酸乙酯和原甲酸三甲酯代替醛，也可以将酯和甲氧基官能团直接安装在嘧啶环上。此外，一系列次硫酸ox鎓盐可提供高收率的产物，从而证明该芳基，杂芳基，以及支链和非支链烷基取代基可以用该试剂引入。最终，在化学转化中首次使用甲酰基亚砜基叶立德使得能够制备仅由醛偶合配偶体引入的在嘧啶环上仅具有单个取代基的产物。对于甲酰基叶立德，使用一锅，逐步反应顺序来防止甲酰基与氨基吡唑竞争性缩合。
• Synthesis of the [3H] labelled potent and selective peripheral benzodiazepine receptor ligand CB 34
  作者：A. Latrofa、G. Trapani、M. Franco、M.J. Harris、M. Serra、G. Biggio、G. Liso

  DOI：10.1002/jlcr.481

  日期：2001.6

  The synthesis of the [3H] labelled peripheral benzodiazepine receptor (PBR) ligand CB 34, useful for binding assay, tissue distribution studies, and elucidation of the physiological role of PBR, is described. Catalytic reduction with 3H2 gas and 10% Pd/C catalyst of the key intermediate 2 afforded the product at a specific activity of 111 Ci/mmol. Copyright © 2001 John Wiley & Sons, Ltd.

  描述了 [3H] 标记的外周苯二氮卓受体 (PBR) 配体 CB 34 的合成，该配体可用于结合测定、组织分布研究和阐明 PBR 的生理作用。用 3H2 气体和 10% Pd/C 催化剂催化还原关键中间体 2，得到比活度为 111 Ci/mmol 的产物。版权所有 © 2001 约翰·威利父子有限公司
• Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors
  作者：Mark R. Burns、C. Lance Carlson、Scott M. Vanderwerf、Josh R. Ziemer、Reitha S. Weeks、Feng Cai、Heather K. Webb、Gerard F. Graminski

  DOI：10.1021/jm0101040

  日期：2001.10.1

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.