4-氟-N-[苄氧羰基]-D-苯丙氨酸 | 117467-73-9

• 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: 4-氟-N-[苄氧羰基]-D-苯丙氨酸
• 中文别名: 苄氧羰基-4-氟-D-苯丙氨酸
• 英文名称: D-Z-4-F-Phe-OH
• 英文别名: (R)-(N-benzyloxycarbonyl)-p-fluorophenylalanine；Cbz-4-fluoro-D-phe；(2R)-3-(4-fluorophenyl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 117467-73-9
• 化学式: C₁₇H₁₆FNO₄
• 分子量: 317.317
• InChiKey: YJSNXFAVHKHBPV-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Cbz-4-fluoro-d-phe
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: Cbz-4-fluoro-d-phe
CAS number: 117467-73-9

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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: C17H16FNO4
Molecular weight: 317.3

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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, hydrogen fluoride.

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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：

  4-氟-N-[苄氧羰基]-D-苯丙氨酸 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 [VCl3(thf)3] 、 铜 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.25h， 生成 [(1R,2S,3S,4R)-4-Benzyloxycarbonylamino-1-(4-fluoro-benzyl)-5-(4-fluoro-phenyl)-2,3-bis-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Preparation and Structure−Activity Relationship of Novel P1/P1‘-Substituted Cyclic Urea-Based Human Immunodeficiency Virus Type-1 Protease Inhibitors

  摘要：

  A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.

  DOI：

  10.1021/jm960083n
• 作为产物：
  描述：

  DL-对氟苯丙氨酸 在 N-甲基吗啉 、 甲醇 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 31.0h， 生成 4-氟-N-[苄氧羰基]-D-苯丙氨酸
  参考文献：
  名称：

  通过金鸡纳生物碱催化的氨基甲酸酯保护的α-氨基酸N-羧基酸酐的动力学拆分，α-氨基酸的不对称合成。

  摘要：

  DOI：

  10.1021/ja011936q

文献信息

• Synthesis, in vitro biological activity, hydrolytic stability and docking of new analogs of BIM-23052 containing halogenated amino acids
  作者：Dancho Danalev、Desislava Borisova、Spaska Yaneva、Maya Georgieva、Anelia Balacheva、Tatyana Dzimbova、Ivan Iliev、Tamara Pajpanova、Zdravka Zaharieva、Ivan Givechev、Emilia Naydenova

  DOI：10.1007/s00726-020-02915-3

  日期：2020.12

  somatostatin analogs, BIM-23052 (DC-23-99) d-Phe-Phe-Phe-d-Trp-Lys-Thr-Phe-Thr-NH2, has established in vitro growth hormone inhibitory activity in nM concentrations. It is also characterized by high affinity to some somatostatin receptors which are largely distributed in the cell membranes of many tumor cells. Herein, we report the synthesis of a series of analogs of BIM-23052 containing halogenated

  一种有效的生长抑素类似物，BIM-23052 (DC-23-99) d -Phe-Phe-Phe- d -Trp-Lys-Thr-Phe-Thr-NH 2, 已在 nM 浓度下建立了体外生长激素抑制活性。它还具有对一些生长抑素受体的高亲和力的特点，这些受体主要分布在许多肿瘤细胞的细胞膜中。在此，我们报告了使用标准固相肽法 Fmoc/OtBu-strategy 合成一系列含有卤化 Phe 残基的 BIM-23052 类似物。在体外针对两种人类肿瘤细胞系（乳腺癌细胞系和肝细胞癌细胞系）以及人类非致瘤性上皮细胞系测试了这些化合物的细胞毒性作用。含有氟苯丙氨酸的类似物在 μM 范围内具有细胞毒性，因为含有 Phe (2-F) 的类似物对人肝细胞癌细胞系显示出更好的选择性。所提出的研究还表明，根据测试的细胞系，卤化 Phe 残基的积累不会增加细胞毒性。计算出的选择性指数揭示了母体化合物 BIM-23052
• Peptide boronic acid compounds useful in anticoagulation
  申请人：Combe-Marzelle Marie Sophie

  公开号：US20050282757A1

  公开（公告）日：2005-12-22

  A method for preventing thrombosis in a setting where rapid onset and/or rapid offset of anticoagulation is required, comprising administering a compound selected from the group consisting of boronic acids which have a neutral thrombin P1 domain linked to a hydrophobic moiety capable of binding to the thrombin S2 and S3 subsites, and pharmaceutically acceptable salts, prodrugs and pharmaceutically acceptable prodrug salts of such acids.

  一种用于在需要快速发生和/或快速停止抗凝的情况下预防血栓形成的方法，包括给予从羟基烷基部位能够结合凝血酶S2和S3亚位点的中性凝血酶P1结构域的硼酸化合物中选择的化合物，以及这些酸的药学上可接受的盐、前药和药学上可接受的前药盐。
• Moriniere, J. L.; Danree, B.; Lemoine, J., Synthetic Communications, 1988, vol. 18, # 4, p. 441 - 444
  作者：Moriniere, J. L.、Danree, B.、Lemoine, J.、Guy, A.

  DOI：——

  日期：——
• [EN] BORONIC ACID THROMBIN INHIBITORS<br/>[FR] INHIBITEURS DE THROMBINE A BASE D'ACIDES BORONIQUES
  申请人：TRIGEN LTD

  公开号：WO2005084687A3

  公开（公告）日：2006-04-20
• Miyazawa, Toshifumi; Iwanaga, Hitoshi; Ueji, Shinichi, Chemistry Letters, 1989, p. 2219 - 2222
  作者：Miyazawa, Toshifumi、Iwanaga, Hitoshi、Ueji, Shinichi、Yamada,Takashi、Kuwata, Shigeru

  DOI：——

  日期：——