N-叔丁氧羰基-L-3-氯苯丙氨酸 | 114873-03-9

• 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: N-叔丁氧羰基-L-3-氯苯丙氨酸
• 中文别名: N-Boc-3-氯-L-苯基丙氨酸；Boc-L-3-氯苯丙氨酸
• 英文名称: (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid
• 英文别名: (2S)-2-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid；Boc-3-chloro-L-phenylalanine；(2S)-3-(3-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 114873-03-9
• 化学式: C₁₄H₁₈ClNO₄
• 分子量: 299.754
• InChiKey: RCZHBTHQISEPPP-NSHDSACASA-N

物化性质

• 熔点：
  110°C
• 沸点：
  452.5±40.0 °C(Predicted)
• 密度：
  1.245

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  S22,S24/25
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-L-3-chlorophenylalanine
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-L-3-chlorophenylalanine
CAS number: 114873-03-9

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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, 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: C14H18ClNO4
Molecular weight: 299.8

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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 chloride.

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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：

  N-叔丁氧羰基-L-3-氯苯丙氨酸 在 PS-carbodiimide resin 、 PS-DIEA resin 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 tert-butyl N-[(2S)-1-[[(2S)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-1-hydroxy-1-(1,3-thiazol-2-yl)pentan-2-yl]amino]-3-(3-chlorophenyl)-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Polymer-Assisted Solution-Phase Library Synthesis and Crystal Structure of α-Ketothiazoles as Tissue Factor VIIa Inhibitors

  摘要：

  A solution-phase synthesis of an alpha-ketothiazole library of the general form D-Phe-L-AA-Arg-alpha-ketothiazole is described. The five-step synthesis is accomplished using a combination of polymeric reagents and polymer-assisted solution-phase purification concepts, including reactant-sequestering resins, reagent-sequestering resins, and tagged reagents. The multistep synthesis affords desired alpha-ketothiazole products in excellent purities and yields. A variety of L-amino acid inputs were used to probe the S-2 pocket of tissue Factor VIIa enzyme to influence both potency and selectivity. An X-ray crystal structure of compound 10k bound to the TF/ VIIa complex was obtained that explains the observed selectivity. The alpha-ketothiazoles were found to be potent, reversible-covalent inhibitors of tissue Factor VIIa, with some analogues demonstrating selectivity over thrombin.

  DOI：

  10.1021/jm030130t

文献信息

• 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。
• Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith
  申请人：D'Sidocky Neil R.

  公开号：US20080242694A1

  公开（公告）日：2008-10-02

  Provided herein are Heterocyclic Compounds having the following structure: wherein R 1 , R 2 , X, Y and Z are as defined herein, compositions comprising an effective amount of a Heterocyclic Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heterocyclic Compound to a patient in need thereof.

  本文提供具有以下结构的杂环化合物： 其中R1、R2、X、Y和Z如本文所定义，包含有效量杂环化合物的组合物，以及治疗或预防癌症、炎症性疾病、免疫疾病、代谢性疾病以及通过给予患者需要的有效量杂环化合物来抑制激酶途径治疗或预防的疾病的方法。
• [EN] GLYT2 MODULATORS<br/>[FR] MODULATEURS DU GLYT2
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005044810A1

  公开（公告）日：2005-05-19

  α-, β-, and Ϝ-amino acid derivatives of formula I are disclosed as selective GlyT2 inhibitors for the treatment of central nervous system (CNS) conditions such as muscle spasticity, tinnitus, epilepsy and neuropathic pain. Formula I

  公式I的α-, β-, 和 Ϝ-氨基酸衍生物被披露为选择性GlyT2抑制剂，用于治疗中枢神经系统（CNS）疾病，如肌肉痉挛、耳鸣、癫痫和神经痛。
• Functionalization of Aromatic Amino Acids via Direct C−H Activation: Generation of Versatile Building Blocks for Accessing Novel Peptide Space
  作者：Falco-Magnus Meyer、Spiros Liras、Angel Guzman-Perez、Christian Perreault、Jianwei Bian、Keith James

  DOI：10.1021/ol1015674

  日期：2010.9.3

  Functionalized α-amino acid building blocks have been prepared in good yield with high regiocontrol and preservation of stereochemistry via iridium-catalyzed borylation of suitably protected aromatic α-amino acid derivatives. The utility of these systems in peptide couplings and Suzuki reactions has been demonstrated.

  已通过铱将适当保护的芳族α-氨基酸衍生物进行硼酸化反应，以高收率，高区域控制性和保持立体化学的高收率制备了功能化的α-氨基酸结构单元。这些系统在肽偶联和铃木反应中的实用性已得到证明。
• [EN] PYRROLIDIN-3-YL COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] COMPOSES PYRROLIDIN-3-YLE UTILES EN TANT QU'INHIBITEURS DE LA BETA-SECRETASE POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：MERCK & CO INC

  公开号：WO2006002004A1

  公开（公告）日：2006-01-05

  The present invention is directed to pyrrolidin-3-yl derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

  本发明涉及吡咯烷-3-基衍生物化合物，这些化合物是β-分泌酶的抑制剂，并且在治疗涉及β-分泌酶的疾病，如阿尔茨海默病中有用。该发明还涉及包含这些化合物的药物组合物，以及在治疗涉及β-分泌酶的这类疾病中使用这些化合物和组合物。