3-乙酰氨基金刚烷-1-甲酸 | 6240-00-2

• 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: 3-乙酰氨基金刚烷-1-甲酸
• 中文别名: 3-乙酰氨基金刚烷-1-羧酸
• 英文名称: 3-acetamidotricyclo[3.3.1.1^3,7]decane-1-carboxylic acid
• 英文别名: 1-acetylaminoadamantane-3-carboxylic acid；3-acetylaminoadamantan-1-carboxylic acid；3-acetamidoadamantanecarboxylic acid；3-(acetylamino)adamantane-1-carboxylic acid；3-acetylamino-adamantane-1-carboxylic acid；1-acetylamino-3-carboxyadamantane；3-acetamidoadamantane-1-carboxylic acid
• CAS: 6240-00-2
• 化学式: C₁₃H₁₉NO₃
• mdl: MFCD00154633
• 分子量: 237.299
• InChiKey: XBMPXAYRLNNWET-UHFFFAOYSA-N

物化性质

• 熔点：
  257-258℃
• 密度：
  1.26±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.846
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Acetylamino-adamantane-1-carboxylic acid
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: 3-Acetylamino-adamantane-1-carboxylic acid
CAS number: 6240-00-2

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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: C13H19NO3
Molecular weight: 237.3

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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.

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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：

  3-乙酰氨基金刚烷-1-甲酸 在 盐酸 、 水 作用下， 反应 144.0h， 以78%的产率得到3-氨基-1-金刚烷甲酸盐酸盐
  参考文献：
  名称：

  ADAMANTYL DIAMIDE DERIVATIVES AND USES OF SAME

  摘要：

  本发明提供了公式（1）的脱氢胆酸二酰胺衍生物：其中R1和R2如本文所定义，或其药用可接受的盐；以及使用相同的药物组合物和方法。

  公开号：

  US20100022546A1
• 作为产物：
  描述：

  1-金刚烷甲酸 、 乙腈 在 硫酸 、 硝酸 作用下， 反应 9.5h， 以83.8%的产率得到3-乙酰氨基金刚烷-1-甲酸
  参考文献：
  名称：

  γ-氨基金刚烷羧酸通过直接 C-H 键酰胺化

  摘要：

  利用不含溴的直接 C-H 键酰胺化，我们合成了多种金刚烷酰胺。根据所使用的前体，这些酰胺在水解裂解后直接产生具有药学活性的氨基金刚烷或 γ-氨基金刚烷羧酸。这些 γ-氨基丁酸 (GABA) 的刚性类似物在 C 端和 N 端受到保护，我们合成了许多在溶液中结合 γ-氨基金刚烷羧酸的肽，以及通过固相肽合成。这些肽是用于药物化学和有机催化应用的有前途的支架。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600975
• 作为试剂：
  描述：

  1-金刚烷甲酸 、 硝酸 、 硫酸 、 乙腈 、 在 ice 、 水 、 3-乙酰氨基金刚烷-1-甲酸 作用下， 以 水 为溶剂， 反应 49.0h， 以to afford 432 g (73%) of the title compound, 3-acetylamino-adamantane-1-carboxylic acid的产率得到3-乙酰氨基金刚烷-1-甲酸
  参考文献：
  名称：

  ADAMANTYL DIAMIDE DERIVATIVES AND USES OF SAME

  摘要：

  本发明提供了公式（1）的孔雀石绿-二酰胺衍生物：其中R1和R2如定义所述，或其药学上可接受的盐；以及使用它们的制药组合物和方法。

  公开号：

  US20100022546A1

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
  申请人：Florjancic S. Alan

  公开号：US20080064699A1

  公开（公告）日：2008-03-13

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R 1 , R 2 , R 3 , R 4 , and L 2 , are defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及式（I）的化合物，或其药学上可接受的盐，前药，前药盐或其组合物，其中R1，R2，R3，R4和L2在规范中有定义，包括这些化合物的组合物，以及使用这些化合物和组合物治疗疾病和病症的方法。
• Invention Concerning Aminoadamantane Compounds
  申请人：Schreiner Peter R.

  公开号：US20080275112A1

  公开（公告）日：2008-11-06

  The present invention describes 1-aminoadamantane derivatives and 3-aminoadamantane-1-carboxylic derivatives in which the 5- or 7-position of the basic adamantane structure can be optionally substituted, methods for the production of the compounds based on the present invention, and methods for the coupling of the monomeric 3-aminoadamantane-1-carboxylic derivatives thus obtained to oligomers. The compounds based on the present invention are suitable for the utilisation as antiviral active ingredients, artificial ion channels, as well as for the therapy, diagnostics and prophylaxis of diseases in which a dysfunction of the GABA system occurs.

  本发明描述了1-氨基金刚烷衍生物和3-氨基金刚烷-1-羧酸衍生物，其中基本金刚烷结构的5-或7-位可以选择性地被取代，基于本发明的化合物的制备方法，以及将单体3-氨基金刚烷-1-羧酸衍生物耦合到寡聚体的方法。基于本发明的化合物适用于作为抗病毒活性成分、人工离子通道，以及治疗、诊断和预防GABA系统功能障碍性疾病。
• NOVEL BRIDGED CYCLIC COMPOUNDS AS HISTONE DEACETYLASE INHIBITORS
  申请人：Balasubramanian Gopalan

  公开号：US20110212943A1

  公开（公告）日：2011-09-01

  Provided herein are novel bridged cyclic derivatives of the general formula (I), their analogs, tautomeric forms, stereoisomers, polymorphs, solvates, intermediates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof. These compounds can inhibit HDACs and are useful as therapeutic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, autoimmune diseases, skin diseases, infections, inflammation, neurode-generative disorders etc.

  本文提供了一种新型的桥联环衍生物，其一般式为(I)，以及它们的类似物、互变异构体、立体异构体、多晶形态、溶剂化物、中间体、药物可接受的盐、药物组合物、代谢物和前药。这些化合物可以抑制HDACs，并且可用作治疗或改善细胞生长相关疾病的药物，例如恶性肿瘤、自身免疫性疾病、皮肤病、感染、炎症、神经退行性疾病等。
• Adamantyl diamide derivatives and uses of same
  申请人：H. Lundbeck A/S

  公开号：US08198275B2

  公开（公告）日：2012-06-12

  The present invention provides adamantyl-diamide derivatives of formula (I): wherein R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof; and pharmaceutical compositions and methods using the same.

  本发明提供了公式（I）的金刚烷基二酰胺衍生物：其中R1和R2的定义如本文所述，或其药学上可接受的盐；以及使用它们的制药组合物和方法。
• Tricomponent Decarboxysulfonylative Cross-coupling Facilitates Direct Construction of Aryl Sulfones and Reveals a Mechanistic Dualism in the Acridine/Copper Photocatalytic System
  作者：Viet D. Nguyen、Ramon Trevino、Samuel G. Greco、Hadi D. Arman、Oleg V. Larionov

  DOI：10.1021/acscatal.2c02332

  日期：2022.7.15

  manifold, comprising a kinetically coupled (via antithetical inhibitory and activating roles of the base in the two catalytic cycles), mechanistically discrete sequence of a photoinduced, acridine-catalyzed decarboxylative process and a thermal copper-catalyzed arylative coupling. The study underscores the importance of non-innocent roles of counteranions and key redox steps at the interface of catalytic cycles

  涉及光催化活化和过渡金属催化步骤的双催化系统使得构建碳-碳和碳-杂原子键的创新方法成为可能。然而，双催化过程的机械复杂性给理解不同催化物种的作用带来了多重挑战，这可能阻碍未来合成方法的发展。在这里，我们报告了一种双重催化过程，通过与芳基卤化物的三组分脱羧磺酰化交叉偶联，能够将以前难以实现的、广泛的、直接的羧酸转化为芳香族砜（最重要的羰基生物等排取代物和合成中间体）。详细的机理和计算研究揭示了铜催化剂、碱、和卤化物阴离子通过独特的双催化歧管引导吖啶/铜系统。与涉及通过低价铜物质协同双重催化的无卤化物脱羧共轭加成相反，卤化物抗衡阴离子通过两相正交中继催化歧管转移与芳基卤化物的脱羧磺酰化交叉偶联，该歧管包含动力学偶联的（通过碱基在两个催化循环中的对立抑制和活化作用），光诱导、吖啶催化脱羧过程和热铜催化芳基化偶联的机械离散序列。