4-羟基-1-甲基双环[2.2.2]辛烷-2-酮 | 5122-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-1-甲基双环[2.2.2]辛烷-2-酮
• 英文名称: NSC-177419
• 英文别名: 4-hydroxy-1-methylbicyclo[2.2.2]octan-2-one
• CAS: 5122-77-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: RZVOELWTDCTKLK-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914400090

SDS

Name:	4-Hydroxy-1-methylbicyclo[2.2.2]octan-2-one 97% Material Safety Data Sheet
Synonym:
CAS:	5122-77-0

Section 1 - Chemical Product MSDS Name:4-Hydroxy-1-methylbicyclo[2.2.2]octan-2-one 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5122-77-0	4-Hydroxy-1-methylbicyclo[2.2.2]octan-	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. 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# 5122-77-0: 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: cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 55 - 56 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: C9H14O2
Molecular Weight: 154

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5122-77-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hydroxy-1-methylbicyclo[2.2.2]octan-2-one - 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# 5122-77-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5122-77-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5122-77-0 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：

  4-羟基-1-甲基双环[2.2.2]辛烷-2-酮 在 N,N-二甲基丙烯基脲 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 Methyl 1-[methoxy(phenyl)methoxy]-4-methyl-3-oxobicyclo[2.2.2]octane-2-carboxylate
  参考文献：
  名称：

  Brown, Christopher J.; Kirby, Anthony J., Journal of the Chemical Society. Perkin transactions II, 1997, # 2, p. 1081 - 1094

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Methoxy-4-methyl-bicyclo<2.2.2>octanon-(3) 在 吡啶盐酸盐 作用下， 生成 4-羟基-1-甲基双环[2.2.2]辛烷-2-酮
  参考文献：
  名称：

  A Novel Method for the Preparation of Bicyclooctane Systems¹

  摘要：

  DOI：

  10.1021/jo01013a057

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20090018114A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的大麻素受体配体，其中A、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• The synthesis of 1,4-disubstituted bicyclo[2.2.2]octanes exhibiting wide-range, enantiotropic nematic phases
  作者：George W. Gray、Stephen M. Kelly

  DOI：10.1039/p29810000026

  日期：——

  The 1,4-disubstituted bicyclo[2.2.2]octane ring has been incorporated in certain cyano-substituted systems to produce series of mesogens exhibiting wide-range nematic phases. 1-(4-Cyanophenyl)- and 1-(4′-cyanobiphenyl-4-yl)-4-n-alkylbicyclo[2.2.2]octanes are colourless stable materials, whose nematic phases are of low birefringence and of positive dielectric anisotropy. This combination of properties

  1,4-二取代的双环[2.2.2]辛烷环已被并入某些氰基取代的系统中，以产生一系列具有宽范围向列相的液晶元。1-（4-氰基苯基）-和1-（4'-氰基联苯-4-基）-4-正烷基双环[2.2.2]辛烷是无色稳定的材料，其向列相具有低双折射和正介电各向异性。这些特性的结合使得这些材料的共晶混合物对电光显示设备具有吸引力，尤其是那些涉及胆甾型-向列相变模式的材料。这些液晶元的液晶转变温度要高于具有1,4-二取代苯环或反式的类似液晶元的液晶转变温度。-1,4-二取代的环己烷环代替1,4-二取代的双环[2.2.2]辛烷环。因此，这些化合物证明了双环[2.2.2]辛烷环具有产生令人感兴趣的向列物质的能力。
• Sterische Einflüsse auf die Dissoziationskonstanten von acyclischen, mono- und bicyclischen Carbonsäuren
  作者：Cyril A. Grob、Thomas Schweizer、Paul Wenk、Rolf S. Wild

  DOI：10.1002/hlca.19770600220

  日期：1977.3.9

  Steric effects on the dissociation constants of acyclic, mono- and bicyclic carboxylic acids

  立体效应对无环，单环和双环羧酸解离常数的影响
• NMR-experiments on acetals—IVL
  作者：H. de Beule、D. Tavernier、M. Anteunis

  DOI：10.1016/s0040-4020(01)97037-1

  日期：1974.1

  Nine 4,4-disubstituted-1,1-dimethoxycyclohexanes have been synthesized. The 4-geminal substituents are: methyl-neopentyl, methyl-cyclohexyl, methyl-benzyl, methyl-vinyl, methyl-phenyl, methyl-chloromethyl, methyl-dichloromethyl, methyl-trichloromethyl, and isopropyl-phenyl.

  已经合成了九种4,4-二取代-1,1-二甲氧基环己烷。4个基团的取代基是：甲基-新戊基，甲基-环己基，甲基-苄基，甲基-乙烯基，甲基-苯基，甲基-氯甲基，甲基-二氯甲基，甲基-三氯甲基和异丙基-苯基。
• Reduktive fragmentierung—III
  作者：W. Kraus、C. Chassin、R. Chassin

  DOI：10.1016/s0040-4020(01)82901-x

  日期：——

  The reduction of 1-methyl-4-tosyloxy-bicyclo[2.2.2]octan-2-one (2) with LAH proceeds by fragmentation to 1-methyl-4-hydroxymethyl-4-methylene-cyclohexane (4) without any influence of the solvent on the product composition. On the other hand the course for the reduction of 1-methy-4-tosyloxy-bicyclol 2.2.2|octanon-2-ethylene acetal (12) depends on the nature of the solvent. Suspensions of LAH in diethyl

  用LAH还原1-甲基-4-甲苯氧基-双环[2.2.2] octan-2-one（2）的过程是通过裂解成1-甲基-4-羟甲基-4-亚甲基-环己烷（4）而进行的溶剂对产品成分的影响。另一方面，还原1-甲基-4-甲苯磺酰氧基-双环基2.2.2 |辛烷-2-乙烯缩醛（12）的过程取决于溶剂的性质。LAH在乙醚中的悬浮液会发生断裂反应，在四氢呋喃中的均相溶液会导致OS键断裂，从而使原始的醇11发生重整。该结果被称为对还原剂的溶剂化作用。