N-乙酰基-L-天冬氨酸 4-叔丁酯 | 117833-18-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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: N-乙酰基-L-天冬氨酸 4-叔丁酯
• 中文别名: N-乙酰基-L-天冬氨酸4-叔丁酯
• 英文名称: Ac-Asp(O-t-Bu)-OH
• 英文别名: (S)-2-acetamido-4-(tert-butoxy)-4-oxobutanoic acid；acetyl-L-aspartic acid β-tert-butyl ester；(2S)-2-acetamido-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
• CAS: 117833-18-8
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: NKNPTCBHHPHSEA-ZETCQYMHSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  449.6±40.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封，在2°C至-8°C下保存

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-asp(otbu)-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-asp(otbu)-oh
CAS number: 117833-18-8

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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: C10H17NO5
Molecular weight: 231.2

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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

制备方法与用途

AC Asp(OtBu)-OH是一种天冬氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  N-乙酰基-L-天冬氨酸 4-叔丁酯 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 三乙胺 作用下， 以 乙醇 、 水 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 48.53h， 生成 司谷氨酸
  参考文献：
  名称：

  Piotrovskii, L. B.; Dumpis, M. A.; Poznyakova, L. N., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 96 - 100

  摘要：

  DOI：
• 作为产物：
  描述：

  L-天门冬氨酸-4-叔丁基酯 、 4-硝基苯基乙酸酯 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以54%的产率得到N-乙酰基-L-天冬氨酸 4-叔丁酯
  参考文献：
  名称：

  Piotrovskii, L. B.; Dumpis, M. A.; Poznyakova, L. N., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 96 - 100

  摘要：

  DOI：

文献信息

• Side-chain protected oligopeptide fragment condensation using subtilisins in organic solvents
  申请人：Quaedflieg Peter Jan Leonard Mario

  公开号：US09598714B2

  公开（公告）日：2017-03-21

  Method for enzymatically synthesizing an oligopeptide, comprising the coupling of an (optionally N-protected) protected oligopeptide ester with an (optionally C-protected) protected oligopeptide nucleophile in an organic solvent or an organic solvent mixture having a water content of 0.1 vol % or less, by a subtilisin in any possible form.

  用酶合成寡肽的方法，包括在有机溶剂或含水量为0.1体积%或更低的有机溶剂混合物中，通过任何可能形式的粗蛋白酶将（可选地N-保护的）保护寡肽酯与（可选地C-保护的）保护寡肽亲核试剂偶联。
• Insertion of an Aspartic Acid Moiety into Cyclic Pseudopeptides:  Synthesis and Biological Characterization of Potent Antagonists for the Human Tachykinin NK-2 Receptor
  作者：Valentina Fedi、Maria Altamura、Giuseppe Balacco、Franca Canfarini、Marco Criscuoli、Danilo Giannotti、Alessandro Giolitti、Sandro Giuliani、Antonio Guidi、Nicholas J. S. Harmat、Rossano Nannicini、Franco Pasqui、Riccardo Patacchini、Enzo Perrotta、Manuela Tramontana、Antonio Triolo、Carlo Alberto Maggi

  DOI：10.1021/jm040832y

  日期：2004.12.1

  A new series of monocyclic pseudopeptide tachykinin NK-2 receptor antagonists has been derived from the lead compound MEN11558. A synthesis for these molecules sharing the same intermediate was designed and performed. The replacement of the succinic moiety with an aspartic acid and the functionalization of its amino group with a wide variety of substituents led to very potent and selective NK-2 antagonists

  从先导化合物MEN11558衍生出一系列新的单环假肽速激肽NK-2受体拮抗剂。设计和执行了这些分子共享相同中间体的合成。用天冬氨酸替换琥珀酸部分，并用多种取代基对其氨基进行官能化，产生了非常有效和选择性的NK-2拮抗剂。最好的结果是通过在R的12位氨基酸上插入一个短间隔基与饱和氮杂环（​​吗啉，哌啶或哌嗪）相连而获得的。该研究产生了化合物54和57，它们在支气管收缩动物模型中以非常低的剂量具有很高的体内效力，并且作用时间长。
• [EN] VEGF NEUTRALIZING PRODRUGS FOR THE TREATMENT OF OCULAR CONDITIONS<br/>[FR] PRO-MÉDICAMENTS DE NEUTRALISATION DE VEGF POUR LE TRAITEMENT D'ÉTATS OCULAIRES
  申请人：ASCENDIS PHARMA OPHTHALMOLOGY DIVISION AS

  公开号：WO2014056923A1

  公开（公告）日：2014-04-17

  The present invention relates to a pharmaceutical composition comprising one or more pharmaceutically acceptable excipient(s) and a VEGF neutralizing prodrug, which comprises a VEGF neutralizing biologically active moiety, for use in a method for the treatment of one or more ocular conditions.

  本发明涉及一种药物组合物，包括一种或多种药用可接受的赋形剂和一种VEGF中和前药，其包括一种VEGF中和生物活性基团，用于治疗一种或多种眼部疾病的方法。
• [EN] PROTECTING GROUP COMPRISING A PURIFICATION TAG<br/>[FR] GROUPE PROTECTEUR COMPRENANT UNE ÉTIQUETTE DE PURIFICATION
  申请人：ASCENDIS PHARMA AS

  公开号：WO2015052155A1

  公开（公告）日：2015-04-16

  The present invention relates to compounds comprising a protecting group moiety-tag moiety conjugate, a method of purification and monoconjugates obtained from such method of purification.

  本发明涉及包含保护基团-标记基团共轭物的化合物，以及一种纯化方法和从该纯化方法获得的单共轭物。
• Predictive Multivariate Linear Regression Analysis Guides Successful Catalytic Enantioselective Minisci Reactions of Diazines
  作者：Jolene P. Reid、Rupert S. J. Proctor、Matthew S. Sigman、Robert J. Phipps

  DOI：10.1021/jacs.9b11658

  日期：2019.12.4

  The Minisci reaction is one of the most direct and versatile methods for forging new carbon–carbon bonds onto basic heteroarenes: a broad subset of compounds ubiquitous in medicinal chemistry. While many Minisci-type reactions result in new stereocenters, control of the absolute stereochemistry has proved challenging. An asymmetric variant was recently realized using chiral phosphoric acid catalysis

  Minisci 反应是在碱性杂芳烃上形成新的碳-碳键的最直接和通用的方法之一：在药物化学中普遍存在的化合物的广泛子集。虽然许多 Minisci 型反应会产生新的立体中心，但绝对立体化学的控制已被证明具有挑战性。最近使用手性磷酸催化实现了不对称变体，尽管在该研究中底物仅限于喹啉和吡啶。机械不确定性和非明显的对映选择性趋势使得将反应扩展到重要的新底物类别的任务具有挑战性且耗时。在此处，我们描述了一种通过精心设计的反应数据集指导并通过多元线性回归 (MLR) 分析促进的反应格局的严格分析来解决这个问题的方法。这些技术允许发展机械信息相关性，为将对映选择性结果转移到新的反应组分提供基础，最终预测嘧啶特别适合该协议。在大多数情况下，对这些有价值的药学相关基序的对映选择性结果的预测非常准确，并导致对范围的全面探索，显着扩展了该方法的实用性和多功能性。