FMOC-顺-4-羟基-D-脯氨酸 | 214852-45-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-顺-4-羟基-D-脯氨酸
• 中文别名: N-芴甲氧羰基-顺式-4-羟基-D-脯氨酸；芴甲氧羰基-顺式-D-脯氨酸
• 英文名称: (4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxy-D-proline
• 英文别名: Fmoc-cis-D-Hyp-OH；Fmoc-D-cis-hyp-OH；(2R,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
• CAS: 214852-45-6
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: GOUUPUICWUFXPM-KZULUSFZSA-N

物化性质

• 沸点：
  595.5±50.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-D-cis-Hyp-OH
Synonyms: (2R,4R)-N-Fmoc-4-hydroxypyrrolidine-2-carboxylic acid

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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: Fmoc-D-cis-Hyp-OH
CAS number: 214852-45-6

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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: C20H19NO5
Molecular weight: 353.4

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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：

  FMOC-顺-4-羟基-D-脯氨酸 在 氯化亚砜 、 sodium carbonate 、 4-氨甲基哌啶 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 3.5h， 生成 (4R)-N-[1-{N'-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-1H-pyrazol-4-yl]-N-ethyl-4-hydroxy-D-prolinamide
  参考文献：
  名称：

  [EN] NOVEL ARYL-CYANOGUANIDINE COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS D'ARYL-CYANOGUANIDINE

  摘要：

  本发明涉及蛋白酰赖氨酸N-甲基转移酶SMYD2（SET和MYND结构域含有蛋白2）抑制剂，特别是通式（I）的SMYD2抑制剂取代氰基胍-吡唑啉，其中R1，R2，R3，R4和R5具有如下所述和定义的含义，以及包含根据本发明的化合物的制药组合物以及它们在高增殖性疾病，特别是癌症，以及肿瘤性疾病的预防和治疗中的预防和治疗用途。本发明还涉及SMYD2抑制剂用于良性增生，动脉粥样硬化性疾病，败血症，自身免疫性疾病，血管疾病，病毒感染，神经退行性疾病，炎症性疾病，动脉粥样硬化性疾病和男性生育控制。

  公开号：

  WO2016166186A1

文献信息

• [EN] MACROCYCLIC PEPTIDES AND DERIVATIVES THEREOF WITH OPIOID ACTIVITY<br/>[FR] PEPTIDES MACROCYCLIQUES ET LEURS DÉRIVÉS À ACTIVITÉ OPIOÏDE
  申请人：UNIV FLORIDA

  公开号：WO2018232285A1

  公开（公告）日：2018-12-20

  The invention relates to macrocyclic peptides and pharmaceutical compositions thereof. The invention further relates to pharmaceutical compositions for modulating opioid receptor activity.

  这项发明涉及大环肽及其药物组合物。该发明还涉及用于调节阿片受体活性的药物组合物。
• Methods for Production of Optically Active Fluoropyrrolidine Derivatives
  申请人：Umemoto Teruo

  公开号：US20100174096A1

  公开（公告）日：2010-07-08

  Useful industrial methods for producing optically active fluoropyrrolidine derivatives as useful fluorinated intermediates are disclosed.

  揭示了用于生产光学活性氟吡咯烷衍生物的有用工业方法，作为有用的氟化中间体。
• Proline Editing: A General and Practical Approach to the Synthesis of Functionally and Structurally Diverse Peptides. Analysis of Steric versus Stereoelectronic Effects of 4-Substituted Prolines on Conformation within Peptides
  作者：Anil K. Pandey、Devan Naduthambi、Krista M. Thomas、Neal J. Zondlo

  DOI：10.1021/ja3109664

  日期：2013.3.20

  ((19)F:fluoro; pentafluorophenyl or perfluoro-tert-butyl ether; 4,4-difluoro; (77)SePh) and other spectroscopies (fluorescence, IR: cyanophenyl ether), leaving groups (sulfonate, halide, NHS, bromoacetate), and other reactive handles (amine, thiol, thioester, ketone, hydroxylamine, maleimide, acrylate, azide, alkene, alkyne, aryl halide, tetrazine, 1,2-aminothiol). Proline editing provides access to these proline

  功能化脯氨酸残基具有多种应用。在此，我们描述了一种实用方法，即脯氨酸编辑，用于合成具有立体特异性修饰的脯氨酸残基的肽。通过标准固相肽合成法合成肽，以掺入 Fmoc-羟脯氨酸 (4R-Hyp)。以自动化方式，Hyp 羟基受到保护，并合成肽的其余部分。肽合成后，Hyp 保护基被正交去除，Hyp 被选择性修饰，生成取代的脯氨酸氨基酸，肽主链起到“保护”脯氨酸氨基和羧基的作用。在模型四肽 (Ac-TYPN-NH2) 中，4R-Hyp 通过 Mitsunobu、氧化、还原、酰化和取代反应立体定向转化为 122 个不同的 4-取代脯氨酰氨基酸，具有 4R 或 4S 立体化学。通过脯氨酸编辑合成的 4-取代脯氨酸包括掺入的结构化氨基酸模拟物（Cys、Asp/Glu、Phe、Lys、Arg、pSer/pThr）、识别基序（生物素、RGD）、诱导立体电子效应的吸电子基团（氟，硝基苯甲酸酯），用于异核 NMR
• [EN] NOVEL 4-FLUOROPYRROLIDINE-2-CARBONYL FLUORIDE COMPOUNDS AND THEIR PREPARATIVE METHODS<br/>[FR] NOUVEAUX FLUORURES DE 4-FLUOROPYRROLIDINE-2-CARBONYLE ET LEURS MÉTHODES DE SYNTHÈSE
  申请人：IM & T RES INC

  公开号：WO2010081014A1

  公开（公告）日：2010-07-15

  Novel 4-fluoropyrrolidine-2-carbonyl fluoride compounds as useful fluorinated intermediates are disclosed. Their preparative methods are also disclosed. Useful applications of the 4-fluoropyrrolidine-2-carbonyl fluorides are shown.

  本发明公开了4-氟吡咯烷-2-羰基氟化物化合物作为有用的氟代中间体。其制备方法也被公开。展示了4-氟吡咯烷-2-羰基氟化物的有用应用。
• Novel 4-Fluoropyrrolidine-2-Carbonyl Fluoride Compounds and Their Preparative Methods
  申请人：Umemoto Teruo

  公开号：US20110275833A1

  公开（公告）日：2011-11-10

  Novel 4-fluoropyrrolidine-2-carbonyl fluoride compounds as useful fluorinated intermediates are disclosed. Their preparative methods are also disclosed. Useful applications of the 4-fluoropyrrolidine-2-carbonyl fluorides are shown.

  本专利公开了一种有用的氟代中间体——4-氟吡咯烷-2-羰基氟化物化合物。同时也公开了它们的制备方法。展示了4-氟吡咯烷-2-羰基氟化物的有用应用。