9H-fluoren-9-ylmethyl N-(6-aminohexyl)carbamate | 166410-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-(6-aminohexyl)carbamate
• 英文别名: Fmoc-1,6-diaminohexane hydrochloride；9H-fluoren-9-ylmethyl-(6-aminohexyl) carbamate；Ν¹-(9-fluorenylmethyloxycarbonyl)-1,6-hexamethylenediamine；mono-Fmoc-1,6-hexanediamine；N1-Fmoc-1,6-diaminohexane；N-Fmoc-1,6-diaminohexane；mono-Fmoc-diaminohexane；Fmoc-1,6-hexandiamine；Fmoc-HDM；Fmoc-hexamethylenediamine hydrochloride；N-Fmoc-hexane-1,6-diamine hydrobromide；Fmoc diaminohexane；Fmoc-1,6-diaminohexane
• CAS: 166410-37-3
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: IRXOHINXQUNLTD-UHFFFAOYSA-N

物化性质

• 沸点：
  529.3±33.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：150 mg/mL（443.21 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-hmd hcl
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: Fmoc-hmd hcl
CAS number: 166410-37-3

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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: C21H26N2O2.ClH
Molecular weight: 374.9

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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

制备方法与用途

生物活性方面，Fmoc-1,6-二氨基己烷是一种类似Osw-1的化合物，具有潜在的应用价值，尤其是在阿尔茨海默症和肿瘤研究领域。该化合物源于专利 US 20140135279 A1。

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-(6-aminohexyl)carbamate 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以45%的产率得到(6-氨基己基)-氨基甲酸 9H-芴-9-基甲基酯
  参考文献：
  名称：

  Flow-Mediated Synthesis of Boc, Fmoc, and Ddiv Monoprotected Diamines

  摘要：

  A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access to N-Boc-, N-Fmoc-, and N-Ddiv-protected compounds with productivity indexes of 1.2-3.6 g/h.

  DOI：

  10.1021/ol503343b
• 作为产物：
  描述：

  N-fluorenylmethoxycarboxnyl-N'-tert-butoxycarbonylhexanediamine 在 苯甲醚 、 三氟乙酸 作用下， 生成 9H-fluoren-9-ylmethyl N-(6-aminohexyl)carbamate
  参考文献：
  名称：

  New series of potent δ-opioid antagonists containing the H-Dmt-Tic-NH-hexyl-NH-R motif

  摘要：

  Heterodimeric compounds H-Dmt-Tic-NH-hexyl-NH-R (R = Dmt, Tic, and Phe) exhibited high affinity to delta-(K-i delta = 0.13-0.89 nM) and p-opioid receptors (K-i mu = 0.38-2.81 nM) with extraordinary potent delta antagonism (pA(2) = 10.2-10.4). These compounds represent the prototype for a new class of structural homologues lacking mu-opioid receptor-associated agonism IC50 = 1.6-5.8 mu M) based on the framework of bis-[H-Dmt-NH]-alkyl (Okada, Y.; Tsuda, Y.; Fujita, Y.; YDkoi, T.; Sasaki, Y.; Ambo, A.; Konishi, R.; Nagata, M.; Salvadori, S.; Jinsmaa, Y.; Bryant, S. D.; Lazarus, L. H. J. Med. Chem. 2003, 46, 3201), which exhibited both high p affinity and bioactivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.073

文献信息

• [EN] MACROCYCLIC COMPOUNDS FOR MODULATING IL-17<br/>[FR] COMPOSÉS MACROCYCLIQUES POUR UNE MODULATION D'IL-17
  申请人：ENSEMBLE THERAPEUTICS CORP

  公开号：WO2013116682A1

  公开（公告）日：2013-08-08

  The invention relates generally to macrocyclic compounds of formula I and their therapeutic use. More particularly, the invention relates to macrocyclic compounds that modulate the activity of IL-17 and/or are useful in the treatment of medical conditions, such as inflammatory diseases and other IL-17-associated disorders.

  这项发明通常涉及公式I的大环化合物及其治疗用途。更具体地，该发明涉及调节IL-17活性的大环化合物，或者用于治疗炎症性疾病和其他与IL-17相关的疾病的大环化合物。
• [EN] PROTEASE-ACTIVATED CONTRAST AGENTS FOR IN VIVO IMAGING<br/>[FR] AGENTS DE CONTRASTE ACTIVÉS PAR UNE PROTÉASE POUR L'IMAGERIE IN VIVO
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2016118910A1

  公开（公告）日：2016-07-28

  Compounds useful as contrast agents in image-guided surgery are provided. The compounds comprise a latent cationic lysosomotropic fragment that is detectable upon cleavage by lysosomal proteases within treated tissues, particularly within tumors and other diseased tissues. Also provided are compositions comprising the compounds and methods for using the compounds, for example in dynamically monitoring protease activity in vivo during image-guided tumor resection surgery.

  提供了作为影像引导手术对比剂有用的化合物。这些化合物包括一种潜在的阳离子溶酶体靶向片段，在治疗组织内被溶酶体蛋白酶裂解后可检测到，特别是在肿瘤和其他患病组织内。还提供了包含这些化合物的组合物和使用这些化合物的方法，例如在影像引导肿瘤切除手术期间动态监测体内蛋白酶活性。
• ANTIBODY DRUG CONJUGATES (ADCS) AND ANTIBODY PRODRUG CONJUGATES (APDCS) WITH ENZYMATICALLY CLEAVABLE GROUPS
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：US20180169256A1

  公开（公告）日：2018-06-21

  The present invention relates to novel binder-prodrug conjugates (APDCs) where binders are conjugated with inactive precursor compounds of kinesin spindle protein inhibitors, and to antibody-drug conjugates ADCs and to processes for producing these APDCs and ADCs.

  这项发明涉及新型结合物-前药偶联物（APDCs），其中结合物与动力蛋白纺锤体抑制剂的非活性前体化合物偶联，以及抗体药物偶联物ADCs以及制备这些APDCs和ADCs的方法。
• 基于蛋白磷酸酶5的磷酸酶募集嵌合体(PHORCs)化合物、其制备方法和医药用途
  申请人：中国药科大学

  公开号：CN113045567B

  公开（公告）日：2023-01-31

  本发明公开如式I所示基于蛋白磷酸酶5的磷酸酶募集嵌合体(PHORCs)化合物、其制备方法和医药用途。本发明的化合物可不同程度的去磷酸化胃癌MKN45细胞中的p‑ASK1，可以在体外、体内显著抑制ASK1活性，从而选择性地下调周期相关蛋白，具有细胞增殖抑制作用。其中化合物DDO‑3711的细胞增殖抑制作用明显优于ASK1小分子抑制剂TCASK10组及ASK1小分子抑制剂TCASK10和PP5小分子激活剂P5SA‑1联合给药组，可用于制备胃癌、结肠癌等相关疾病的治疗药物。
• [EN] CXCR4-TARGETED DIAGNOSTIC AND THERAPEUTIC AGENTS WITH REDUCED SPECIES SELECTIVITY<br/>[FR] AGENTS THÉRAPEUTIQUES ET DIAGNOSTIQUES DIRIGÉS CONTRE LE CXCR4 À SÉLECTIVITÉ D'ESPÈCES RÉDUITE
  申请人：UNIV MUENCHEN TECH

  公开号：WO2020053256A1

  公开（公告）日：2020-03-19

  The present disclosure relates to imaging and endoradiotherapy of diseases involving chemokine receptor 4 (CXCR4). Provided are compounds which bind or inhibit hCXCR4 and mCXCR4 and furthermore carry at least one moiety which is amenable to labeling. Provided are also medical uses of such compounds.

  本公开涉及与化学因子受体4（CXCR4）有关的疾病的成像和内部放射治疗。提供了结合或抑制hCXCR4和mCXCR4的化合物，而且这些化合物还携带至少一个适合标记的基团。还提供了这些化合物的医疗用途。