3,5,7-三甲基金刚烷-1-羧酸 | 15291-66-4

• 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: 3,5,7-三甲基金刚烷-1-羧酸
• 英文名称: 3,5,7-trimethyladamantanecarboxylic acid
• 英文别名: 3,5,7-trimethyl-1-adamantanecarboxylic acid；3,5,7-Trimethyladamantane-1-carboxylic acid
• CAS: 15291-66-4
• 化学式: C₁₄H₂₂O₂
• mdl: MFCD00187581
• 分子量: 222.327
• InChiKey: DHIIUPVOLLOORM-UHFFFAOYSA-N

物化性质

• 熔点：
  139-141 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  334.8±10.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.928
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2916209090

SDS

Name:	3 5 7-Trimethyladamantane-1-carboxylic acid 97% Material Safety Data Sheet
Synonym:
CAS:	15291-66-4

Section 1 - Chemical Product MSDS Name:3 5 7-Trimethyladamantane-1-carboxylic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15291-66-4	3,5,7-Trimethyladamantane-1-carboxylic	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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. Immediately 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.
Ingestion:
Get medical aid. 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:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 15291-66-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 149 - 151 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C14H22O2
Molecular Weight: 222.33

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15291-66-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,5,7-Trimethyladamantane-1-carboxylic acid - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 15291-66-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15291-66-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15291-66-4 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

反应信息

• 作为反应物：
  描述：

  3,5,7-三甲基金刚烷-1-羧酸 在 lithium aluminium tetrahydride 、 Glauber's salt 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以87%的产率得到2-(3,5,7-trimethyladamantan-1-yl)ethan-1-ol
  参考文献：
  名称：

  开环明酰胺类似物对耐甲氧西林金黄色葡萄球菌†的合成及其构效关系†

  摘要：

  耐甲氧西林金黄色葡萄球菌（MRSA）已成为对公共卫生的主要威胁，因为临床分离出的菌株对多种抗生素具有耐药性。因此，开发用于治疗MRSA感染的新抗生素是持续的挑战。先前我们已经确定了开环的苯甲酰胺类似物L472-2，其对金黄色葡萄球菌的生长具有中等活性。在我们之前的工作中，我们从L472-2开始，鉴定出一类含有炔基的类似物，这些类似物具有激活SaClpP活性但具有中等抗菌活性的潜力。在这里，我们集中于L472-2的抗菌活性，合成了一系列新的开环的苯甲酰胺类似物，并评估了它们对MRSA的活性。通过对这些类似物的构效关系（SAR）进行紧凑分析，我们发现金刚烷乙醇酯苯甲酰胺2j对包括MRSA在内的6种金黄色葡萄球菌菌株均显示出优异的抗菌活性，但它并未激活ClpP。因此，这些苯甲酰胺类似物代表了抑制MRSA生存力的一类新候选人。

  DOI：

  10.1002/cjoc.202000502
• 作为产物：
  描述：

  p-Toluolsulfonat des 3.5-Dimethyl-1-hydroxymethyl-adamantans 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 叔丁醇 为溶剂， 生成 3,5,7-三甲基金刚烷-1-羧酸
  参考文献：
  名称：

  Koch,H.; Franken,J., Chemische Berichte, 1963, vol. 96, p. 213 - 219

  摘要：

  DOI：

文献信息

• Directed C−H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate
  作者：Marta Larrosa、Benjamin Zonker、Jannis Volkmann、Felix Wech、Christian Logemann、Heike Hausmann、Radim Hrdina

  DOI：10.1002/chem.201800550

  日期：2018.4.20

  We have developed a synthesis of 1,2‐substituted adamantane carboxylic acids and further bridged cycloalkanes (cage compounds) by palladium acetate‐catalyzed C−H bond oxidation. Acetoxylation of cycloalkane framework was performed using picolylamide as a directing group. Modification of the substrate, ligand design and variation of reaction conditions enabled us to study the mechanism of acetoxylation

  我们已经开发出一种通过乙酸钯催化的CH键氧化反应合成1,2-取代的金刚烷羧酸和进一步桥连的环烷烃（笼型化合物）的方法。环烷构架的乙酰氧基化是使用吡啶甲基酰胺作为指导基团进行的。底物的修饰，配体设计和反应条件的变化使我们能够研究脂肪族化合物乙酰氧基化的机理。开发了官能团后反应和导向基团的裂解。首次一个β-的合成和表征Ç 3 -三金刚烷取代衍生物达到了。
• Bicycloheteroaryl compounds as P2X7 modulators and uses thereof
  申请人：Kelly G. Michael

  公开号：US20060217448A1

  公开（公告）日：2006-09-28

  Bicycloheteroaryl compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.

  公开了具有以下公式代表的Bicycloheteroaryl化合物：这些化合物可以制备为药物组合物，并可用于预防和治疗包括人类在内的哺乳动物的各种疾病，例如疼痛、炎症、创伤性损伤等。
• PROCESS FOR PRODUCING PHENYL-SUBSTITUTED HETEROCYCLIC DERIVATIVE THROUGH COUPLING USING TRANSITION METAL CATALYST
  申请人：Komiyama Masato

  公开号：US20110313169A1

  公开（公告）日：2011-12-22

  A process for efficiently producing, through few steps either a xanthine oxidase inhibitor, which is a therapeutic agent for hyperuricemia, or an intermediate therefore. The process is a novel coupling process which comprises subjecting a compound represented by formula (1) to coupling reaction with a compound represented by formula (2) in the presence of a transition metal compound to thereby obtain a compound represented by formula (3).

  一种高效生产黄嘌呤氧化酶抑制剂或其中间体的方法，该抑制剂是治疗高尿酸血症的药物。该方法是一种新型偶联过程，包括将式（1）表示的化合物与式（2）表示的化合物在过渡金属化合物存在下进行偶联反应，从而获得式（3）表示的化合物。
• Adamantyl- and other polycyclic cage-based conjugates of desferrioxamine B (DFOB) for treating iron-mediated toxicity in cell models of Parkinson’s disease
  作者：Thomas J. Telfer、Jeffrey R. Liddell、Clare Duncan、Anthony R. White、Rachel Codd

  DOI：10.1016/j.bmcl.2017.03.001

  日期：2017.4

  facilitate intracellular iron sequestration. The first activity screen showed compounds with methyl-substituted adamantyl (1-3), noradamantyl (5), or 1-pentylbicyclo[2.2.2]octane (17) ancillary groups significantly rescued iron-mediated oxidative stress in confluent PD-relevant SK-N-BE2-M17 neuroblastoma cells (M17 cells) exposed to 1,1'-dimethyl-4,4'-bipyridinium (paraquat, PQ) or H2O2. The second dose-dependence

  多巴胺能神经元的死亡是帕金森氏病（PD）的主要病理标志。PD脑黑质内的铁被认为可通过羟基自由基引起的氧化损伤来催化这种神经元死亡。去除这种过量的铁代表了PD的潜在治疗策略。通过金刚烷基-（1-4，8-12），解构的金刚烷基单元（5-7），降冰片（e）ne-（13- 16）或末端胺基的双环[2.2.2]辛烷基（17）辅助片段。实验logP值的范围为1-17（logP = 0.15-2.82）大于水溶性DFOB（logP -2.29），疏水性增加，旨在改善细胞膜的转运，促进细胞内铁的螯合。首次活性筛选显示，具有甲基取代的金刚烷基（1-3），去甲金刚烷基（5）或1-戊基双环[2.2.2]辛烷（17）辅助基团的化合物可在与PD相关的汇合性SK中显着缓解铁介导的氧化应激-N-BE2-M17神经母细胞瘤细胞（M17细胞）暴露于1,1'-二甲基-4,4'-联吡啶鎓（百草枯，PQ）或H2O2。在对PQ处理
• 1-(adamantyl)amidines and their use in the treatment of conditions generally associated with abnormalities in glutamatergic transmission
  申请人：Vernalis Research Limited

  公开号：US06500866B1

  公开（公告）日：2002-12-31

  Compounds of 1-(adamantyl) amidine and their use in the treatment of conditions generally associated with abnormalities in glutamatergic transmittion.

  1-(戊二醇基)胺基甲酸盐类化合物及其在治疗通常与谷氨酸能传递异常相关的疾病中的用途。