N-芴甲氧羰基-L-苯丙氨酸五氟苯酯 | 86060-92-6

• 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-芴甲氧羰基-L-苯丙氨酸五氟苯酯
• 中文别名: FMOC-L-苯丙氨酸五氟苯酯；N-(9-芴基甲氧基羰基)-L-苯丙氨酸五氟苯酯
• 英文名称: N-α-Fmoc-L-phenylalanine pentafluorophenyl ester
• 英文别名: Fmoc-Phe-OPfp；Fmoc-phenylalanine pentafluorophenyl ester；(2,3,4,5,6-pentafluorophenyl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoate
• CAS: 86060-92-6
• 化学式: C₃₀H₂₀F₅NO₄
• 分子量: 553.485
• InChiKey: WKHPSOMXNCTXPK-QFIPXVFZSA-N

物化性质

• 熔点：
  149-151 °C(lit.)
• 沸点：
  674.8±55.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 稳定性/保质期：
  按规定使用和贮存的这些物质不会分解，并应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  9

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2924 29 70
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  建议存储在2-8°C的环境中，并保持容器密封和置于干燥处。

SDS

Name:	N-(9-Fluorenylmethoxycarbonyl)-L-Phenylalanine Pentafluorophenyl Material Safety Data Sheet
Synonym:	None
CAS:	86060-92-6

Section 1 - Chemical Product MSDS Name:N-(9-Fluorenylmethoxycarbonyl)-L-Phenylalanine Pentafluorophenyl Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
86060-92-6	N-(9-Fluorenylmethoxycarbonyl)-L-pheny	ca 100	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 86060-92-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 151 - 152 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C30H20F5NO4
Molecular Weight: 553.49

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 86060-92-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-(9-Fluorenylmethoxycarbonyl)-L-phenylalanine pentafluoroph - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 86060-92-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 86060-92-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 86060-92-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Fmoc-Phe OPfp是一种苯丙氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基-L-苯丙氨酸五氟苯酯 生成 L-苯丙氨酰胺
  参考文献：
  名称：

  Funakoshi, Susumu; Murayama, Eigoro; Guo, Lili, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2791 - 2800

  摘要：

  DOI：
• 作为产物：
  描述：

  9-芴甲基五氟苯基碳酸酯 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 2.0h， 生成 N-芴甲氧羰基-L-苯丙氨酸五氟苯酯
  参考文献：
  名称：

  Schoen, Istvan; Kisfaludy, Lajos, Synthesis, 1986, # 4, p. 303 - 305

  摘要：

  DOI：
• 作为试剂：
  描述：

  methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate 在 palladium dihydroxide 盐酸 、 三氟甲磺酸三甲基硅酯 、 氢气 、 N-芴甲氧羰基-L-苯丙氨酸五氟苯酯 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 96.0h， 生成 3,7-anhydro-2-deoxy-3-C-(aminomethyl)-D-glycero-L-manno-octonic acid lactam
  参考文献：
  名称：

  Synthesis of a galacto-configured C-ketoside-based γ-sugar-amino acid and its use in peptide coupling reactions

  摘要：

  gamma-Sugar-amino acid analogues in the form of C-ketosides can be prepared in 5-6 steps starting from D-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting beta-cyano esters provides C-ketoside-based gamma-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.006

文献信息

• [EN] POLYCONJUGATES FOR DELIVERY OF RNAI TRIGGERS TO TUMOR CELLS IN VIVO<br/>[FR] POLYCONJUGUÉS POUR L'ADMINISTRATION DE DÉCLENCHEURS D'ARNI À DES CELLULES TUMORALES IN VIVO
  申请人：ARROWHEAD RES CORP

  公开号：WO2015021092A1

  公开（公告）日：2015-02-12

  The present invention is directed compositions for delivery of RNA interference (RNAi) triggers to integrin positive tumor cells in vivo. The compositions comprise RGD ligand- targeted amphipathic membrane active polyamines reversibly modified with enzyme cleavable dipeptide-amidobenzyl-carbonate masking agents. Modification masks membrane activity of the polymer while reversibility provides physiological responsiveness. The reversibly modified polyamines (dynamic polyconjugate or conjugate) are further covalently linked to an RNAi trigger.

  本发明涉及将RNA干扰（RNAi）触发物传递至体内整合素阳性肿瘤细胞的组合物。这些组合物包括以RGD配体为靶向的两性膜活性多胺，可逆地修饰为酶可切割二肽-酰胺基苄-碳酸酯掩蔽剂。修饰掩盖了聚合物的膜活性，而可逆性提供了生理响应性。这些可逆修饰的多胺（动态多共轭物或共轭物）进一步与RNAi触发物共价连接。
• Enantioselection in peptide bond formation
  作者：Roger R. Hill、David Birch、Graham E. Jeffs、Michael North

  DOI：10.1039/b211914e

  日期：2003.3.13

  Selectivity in abiotic condensations of amino acids remains controversial and stereochemically little explored. We find that competitive activated couplings of N-acyl derivatives of glycine, alanine, valine, proline and phenylalanine with binary, ternary and quaternary mixtures of amides and esters of the same group of amino acids show little selectivity among the reactants, except with respect to configuration, where a consistent and significant preference for heterochiral outcomes, mostly >80%, is observed. One possible explanation of this selectivity predicts a predisposition to homochiral coupling under conditions that would require the two carboxyl functions to be co-facial in the activated complex.

  无机物促成的氨基酸缩聚反应中选择性仍然备受争议，而立体化学方面的研究甚少。我们发现，以酰胺和酯组成的双组分、三组分以及四组分混合物为底物，对甘氨酸、丙氨酸、缬氨酸、脯氨酸和苯丙氨酸的N-酰基衍生物进行竞争性活化偶联的反应中，产物在底物分子层面选择性较低，但对映异构选择性较高，选择性系数大多大于80%。此类反应中优先生成异手性产物的一种可能的解释是，在两个羧基必须共面的活化复合物中，同手性偶联具有倾向性。
• A new facile one-pot preparation of pentafluorophenyl (Pfp) and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl (Dhbt) esters of Fmoc amino acids.
  作者：Mogens Havsteen Jacobsen、Ole Buchardt、Tom Engdahl、Arne Holm

  DOI：10.1016/0040-4039(91)80788-8

  日期：1991.10

  A new one-pot procedure for the preparation of pentafluorophenyl and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl esters of Nα-9-fluorenylmethyloxycarbonyl amino acids bearing no side chain protecting groups is described. The method gives the desired activated esters in high yield and purity without use of the highly allergenic DCC.

  对于N五氟苯基和3,4-二氢-4-氧代-1,2,3-苯并三嗪-3-基酯的制备的新的一锅程序α -9-芴氨基酸不带有侧链保护基团是描述。该方法无需使用高度致敏的DCC，即可以高收率和纯度获得所需的活化酯。
• Peptide Synthesis with α-(Difluoromethyl)-Substituted α-Amino Acids
  作者：Thomas Michel、Beate Koksch、Sergei N. Osipov、Alexander S. Golubev、Joachim Sieler、Klaus Burger

  DOI：10.1135/cccc20021533

  日期：——

  Methodology for the incorporation of α-(difluoromethyl)-substituted α-amino acids into N- and C-terminal positions of dipeptides as well as into position 2 of tri- and tetrapeptides is described.

  将α-(二氟甲基)-取代的α-氨基酸并入二肽的N-和C-末端位置，以及并入三肽和四肽的位置2的方法被描述。
• Peptidotriazoles on Solid Phase:  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
  作者：Christian W. Tornøe、Caspar Christensen、Morten Meldal

  DOI：10.1021/jo011148j

  日期：2002.5.1

  The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely

  叠氮化物与炔烃的环加成反应是合成1H- [1,2,3]-三唑的最重要合成途径之一。在这里报道了一种新型的区域特异性铜（I）催化的末端炔烃在固相上与叠氮化物的1,3-偶极环加成反应。伯，仲和叔烷基叠氮化物，芳基叠氮化物和叠氮糖已成功用于铜（I）催化的环加成反应中，在肽主链或侧链上产生了不同的1,4-取代的[1,2,3]-三唑。反应条件与极性载体上的固相肽合成完全相容。铜（I）催化反应温和有效（大多数情况下> 95％的转化率和纯度），此外，2-叠氮基-2-甲基丙酸的X射线结构得到了解析，以得到有关1， 3-偶极子进入反应。