2,2,6-三甲基环己酮 | 2408-37-9

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酮(含烯醇)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2,6-三甲基环己酮
• 中文别名: 2,2,6-三甲基环庚烷
• 英文名称: 2,2,6-trimethylcyclohexan-1-one
• 英文别名: 2,2,6-trimethylcyclohexanone；2,6,6-trimethylcyclohexanone；2,6,6-trimethyl-cyclohexan-1-one
• CAS: 2408-37-9
• 化学式: C₉H₁₆O
• mdl: MFCD00045550
• 分子量: 140.225
• InChiKey: ZPVOLGVTNLDBFI-UHFFFAOYSA-N

物化性质

• 熔点：
  -31.8°C
• 沸点：
  178-179 °C(lit.)
• 密度：
  0.904 g/mL at 25 °C(lit.)
• 闪点：
  125 °F
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  2.41
• 物理描述：
  Liquid
• 折光率：
  1.443-1.449
• 保留指数：
  1013;1008;1008;1019;1022;1011;1035;1017;1011;1019;1029;1016;1007;1012;1012
• 稳定性/保质期：
  - 避免氧化物接触。 - 存在于烤烟烟叶、香料烟烟叶、主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 安全说明：
  S23,S24/25
• 危险类别码：
  R10
• WGK Germany：
  3
• 海关编码：
  2914299000
• 包装等级：
  III
• 危险类别：
  3
• 危险品运输编号：
  UN 1224 3/PG 3
• 储存条件：
  请将容器密封，并将其存放在紧密封装的容器中，确保储存于阴凉、干燥的地方。

SDS

Name:	2 2 6-Trimethylcyclohexanone 98.5+% (GC) Material Safety Data Sheet
Synonym:	2,2,6-Trimethylcyclohexan-1-one; Cyclohexanone, 2,2,6-trimethyl-; Trimethylcyclohexanon
CAS:	2408-37-9

Section 1 - Chemical Product MSDS Name:2 2 6-Trimethylcyclohexanone 98.5+% (GC) Material Safety Data Sheet
Synonym:2,2,6-Trimethylcyclohexan-1-one; Cyclohexanone, 2,2,6-trimethyl-; Trimethylcyclohexanon

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2408-37-9	2,2,6-Trimethylcyclohexanone (GC)	98.5+	219-309-9

Hazard Symbols: None Listed.
Risk Phrases: 10

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. May cause chemical conjunctivitis and corneal damage.
Skin:
May cause irritation and dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. Ingestion of large amounts may cause CNS depression.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Aspiration may lead to pulmonary edema. Vapors may cause dizziness or suffocation.
May cause burning sensation in the chest.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: 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. 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.
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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire. Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Water may be ineffective. Use agent most appropriate to extinguish fire. Do NOT use straight streams of water. 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:
Cover with sand, dry lime or soda ash and place in a closed container for disposal. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. A vapor suppressing foam may be used to reduce vapors.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep away from heat, sparks and flame.
Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 2408-37-9: 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: Clear liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 61.0 - 62.0 deg C @ 15.00mm H
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 51 deg C ( 123.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: .9040g/cm3
Molecular Formula: C19H16O
Molecular Weight: 260.33

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2408-37-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,2,6-Trimethylcyclohexanone (GC) - 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
Shipping Name: KETONES, LIQUID, N.O.S.*
Hazard Class: 3
UN Number: 1224
Packing Group: III
IMO
Shipping Name: KETONES, LIQUID, N.O.S.
Hazard Class: 3.3
UN Number: 1224
Packing Group: III
RID/ADR
Shipping Name: KETONES, N.O.S.
Hazard Class: 3
UN Number: 1224
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
R 10 Flammable.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
WGK (Water Danger/Protection)
CAS# 2408-37-9: No information available.
Canada
CAS# 2408-37-9 is listed on Canada's DSL List.
CAS# 2408-37-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2408-37-9 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

食品添加剂最大允许使用量与最大允许残留量标准 表格内容

添加剂中文名称	允许使用该种添加剂的食品中文名称	添加剂功能	最大允许使用量（g/kg）	最大允许残留量（g/kg）
2,2,6-三甲基环己酮	食品	食用药香料	用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量	-

请注意，上述信息中的“食品”一词重复列出，在实际应用中应予以修正。

反应信息

• 作为反应物：
  描述：

  2,2,6-三甲基环己酮 在 氢氧化钾 、 敌草腈 、 碘 、 叔丁基锂 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正戊烷 为溶剂， 反应 22.5h， 生成 9-顺式维甲酸
  参考文献：
  名称：

  9-顺-视黄酸及其环脱甲基类似物的立体控制合成中的铃木偶联反应。

  摘要：

  enyl加速碘化四烯基碘化物19和环己烯基硼酸酯18的Suzuki偶联反应，可高产率获得9-顺式-视黄酸乙酯（12）。Suzuki反应的两个偶合伙伴在从其前体四烯基锡烷10和环己烯基碘13生成后，立即能更好地反应。在几何上均匀的四烯基锡烷10包括9-顺-视黄酸乙酯及其环脱甲基类似物的多烯侧链。由立体选择性霍纳-沃兹沃思-埃蒙斯反应合成。另一方面，容易获得的环己酮是制备合成环修饰的9-顺-视黄酸类似物所需的环己烯基硼酸酯的理想起始原料。对于受阻的环己酮，将azo酮转化为环己烯基碘化物。然后进行碘-锂交换并用B（OMe）（3）捕集，得到环己烯基硼酸酯。如果前体环己酮具有仲碳，则通过消除在用正丁基锂处理三甲hydr时获得的C，N-二甲硅烷基化的中间体（Shapiro反应）来方便地形成烯基锂物质。上述方法均不能使2-甲基环己酮生成更多取代的有机锂。但是，交替的34和10的Stille交叉偶联得到9

  DOI：

  10.1021/jo010711v
• 作为产物：
  描述：

  2,6,6-三甲基-2-环己烯-1,4-二酮 在 氢气 作用下， 以16%的产率得到2,2,6-三甲基环己酮
  参考文献：
  名称：

  Method for synthesis of 2,2,6-trimethylcyclohexan-1-one

  摘要：

  本发明涉及一种通过在气相中在氧化物催化剂存在下对2,6,6-三甲基-2-环己烯-1,4-二酮（酮异香叶酮，KIP）进行部分还原来合成2,2,6-三甲基环己烷-1-酮（TMCH）的方法。

  公开号：

  US20050027142A1

文献信息

• Enantioselective Decarboxylative Alkylation Reactions: Catalyst Development, Substrate Scope, and Mechanistic Studies
  作者：Douglas C. Behenna、Justin T. Mohr、Nathaniel H. Sherden、Smaranda C. Marinescu、Andrew M. Harned、Kousuke Tani、Masaki Seto、Sandy Ma、Zoltán Novák、Michael R. Krout、Ryan M. McFadden、Jennifer L. Roizen、John A. Enquist、David E. White、Samantha R. Levine、Krastina V. Petrova、Akihiko Iwashita、Scott C. Virgil、Brian M. Stoltz

  DOI：10.1002/chem.201003383

  日期：2011.12.9

  functions with nearly identical efficiency in terms of yield and enantioselectivity. Catalyst discovery and development, the optimization of reaction conditions, the exploration of reaction scope, and applications in target‐directed synthesis are reported. Experimental observations suggest that these alkylation reactions occur through an unusual inner‐sphere mechanism involving binding of the prochiral

  在钯配合物与各种膦恶唑啉 (PHOX) 配体的存在下，通过不稳定的前手性烯醇化亲核试剂对烯丙基和炔丙基亲电子试剂进行新颖的对映选择性烷基化来获得 α-季酮。三类烯醇化物前体获得了优异的产率和高对映体过量：烯醇碳酸酯、烯醇硅烷和外消旋 β-酮酯。这些底物类别中的每一种在产率和对映选择性方面都具有几乎相同的效率。报道了催化剂的发现和开发、反应条件的优化、反应范围的探索以及在靶向合成中的应用。实验观察表明，这些烷基化反应通过一种不寻常的内球机制发生，涉及前手性烯醇化亲核试剂直接与钯中心结合。
• Catalytic Allylic Oxidation to Generate Vinylogous Acyl Sulfonates from Vinyl Sulfonates
  作者：James K. Tucker、Matthew D. Shair

  DOI：10.1021/acs.orglett.9b00845

  日期：2019.4.5

  formation of vinylogous acyl sulfonates was accomplished via the allylic oxidation of the corresponding vinyl sulfonates. The reaction progressed through the agency of catalytic iron(III) chloride catalysis with tert-Butyl hydroperoxide (TBHP) as the stoichiometric oxidant. Tolerance of other functional groups, including some other allylic and benzylic sites, was observed.

  乙烯基酰基磺酸盐的区域选择性形成是通过相应乙烯基磺酸盐的烯丙基氧化完成的。该反应通过催化氯化铁（III）的催化作用进行，其中叔丁基过氧化氢（TBHP）为化学计量的氧化剂。观察到对其他官能团的耐受性，包括一些其他的烯丙基和苄基位点。
• [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] LIGANDS DE LIAISON À UNE OPSINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2013058809A1

  公开（公告）日：2013-04-25

  Compounds are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.

  披露了一些化合物，可用于治疗由于或与在眼睛中积累的有毒视觉循环产物有关的眼科疾病，例如干性成人黄斑变性，以及由于或与突变视蛋白的错误折叠和/或视蛋白的错误定位有关的疾病。还描述了这些化合物单独或与其他治疗剂联合使用的组合物，以及使用这些化合物和/或组合物的治疗方法。还披露了合成这些药剂的方法。
• [EN] INDANYLOXYDIHYDROBENZOFURANYLACETIC ACIDS<br/>[FR] ACIDES INDANYLOXYDIHYDROBENZOFURANYLACÉTIQUES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012072691A1

  公开（公告）日：2012-06-07

  The present invention relates to compounds defined by formula (I) wherein the variables R1, R2, R3, m, and n are defined as in claim 1, possessing valuable pharmacological activity. Particularly, the compounds are activators of the receptor GPR40 and thus are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及具有式(I)定义的化合物，其中变量R1、R2、R3、m和n如权利要求1中定义，具有宝贵的药理活性。特别是，这些化合物是GPR40受体的激动剂，因此适合用于治疗和预防可以通过这种受体影响的疾病，例如代谢性疾病，特别是2型糖尿病。
• Substituierte Propargylcarbinole und ihre hypnotische Wirkung
  作者：H. Gutmann、O. Isler、G. Ryser、P. Zeller、B. Pellmont

  DOI：10.1002/hlca.19590420312

  日期：——

  Thirty tertiary propargylic carbinols have been prepared by condensing propargyl bromide with ketones. Some of them showed better hypnotic activity than 3-methylpentyn-3-01. The best compound of the series was 1-chloro-2-chloromethylpent-4-yn-2-01 which proved to be a very effective hypnotic with a favourable therapeutic index.

  通过使炔丙基溴与酮缩合制备了三十种叔炔丙基甲醇。其中一些表现出比3-甲基戊炔-3-01更好的催眠活性。该系列中最好的化合物是1-氯-2-氯甲基戊-4-yn-2-01，事实证明它是一种非常有效的催眠药，具有良好的治疗指数。

表征谱图