2-溴-1-环己基乙酮 | 56077-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-1-环己基乙酮
• 中文别名: 2-溴-1-环已基乙酮
• 英文名称: Bromomethyl cyclohexyl ketone
• 英文别名: 2-bromo-1-cyclohexylethanone
• CAS: 56077-28-2
• 化学式: C₈H₁₃BrO
• mdl: MFCD08444491
• 分子量: 205.095
• InChiKey: ADLIDZNESKOPIP-UHFFFAOYSA-N

物化性质

• 熔点：
  -3.5-2 °C
• 沸点：
  124-125 °C(Press: 25 Torr)
• 密度：
  1.359

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-1-cyclohexylethanone
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: 2-Bromo-1-cyclohexylethanone
CAS number: 56077-28-2

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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, refrigerated.
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: C8H13BrO
Molecular weight: 205.1

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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, hydrogen bromide.

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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：

  2-溴-1-环己基乙酮 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 甲醇 、 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以55%的产率得到2-环己基环氧乙烷
  参考文献：
  名称：

  通过将锂化的环氧化合物插入硼酸酯中来迭代合成烯烃。

  摘要：

  锂化的环氧化物的插入硼酸酯，随后通过热合成在剔除提供立体有择的条目为烯烃。该过程避免了过渡金属，并且易于迭代以提供更高的取代模式。

  DOI：

  10.1021/acs.orglett.9b00517
• 作为产物：
  描述：

  乙酰基环己烷 在 溴 作用下， 以 甲醇 为溶剂， 以90%的产率得到2-溴-1-环己基乙酮
  参考文献：
  名称：

  A focused structure–activity relationship study of psoralen-based immunoproteasome inhibitors

  摘要：

  在紫草素环的单个位置进行结构活性关系（SAR）探索，导致对免疫蛋白酶体的胰蛋白酶样（β5i）亚基的选择性提高。

  DOI：

  10.1039/c9md00365g
• 作为试剂：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile 在 lithium hexamethyldisilazane 2-溴-1-环己基乙酮 、 碳酸氢钠 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 78.0h， 生成 5-(4-Chloro-phenyl)-3-(5-cyclohexyl-1H-imidazol-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole
  参考文献：
  名称：

  Cannabinoid receptor ligands and uses thereof

  摘要：

  本文描述了作为大麻素受体配体的化合物（I）及其在治疗与动物体内大麻素受体调节相关疾病中的用途。

  公开号：

  US20040077650A1

文献信息

• Catalytic dehydrogenative dual functionalization of ethers: dealkylation–oxidation–bromination accompanied by C–O bond cleavage via aerobic oxidation of bromide
  作者：Katsuhiko Moriyama、Tsukasa Hamada、Yu Nakamura、Hideo Togo

  DOI：10.1039/c7cc02166f

  日期：——

  A catalytic dehydrogenative dual functionalization (DDF) of ethers via oxidation, dealkylation, and α-bromination by the aerobic oxidation of bromide was developed to obtain the corresponding α-bromo ketones in high yields. In particular, the reaction of substituted tetrahydrofurans as cyclic ethers provided 3,3-dibromo tetrahydrofuran-2-ols in high yields selectively through the double α-bromination

  通过溴的需氧氧化，通过氧化，脱烷基和α-溴化反应，开发了醚的催化脱氢双官能化（DDF），以高收率获得了相应的α-溴代酮。特别地，取代的四氢呋喃作为环醚的反应通过双α-溴化选择性地以高收率提供了3,3-二溴四氢呋喃-2-醇。
• Palladium‐Catalyzed Decarboxylative Alkynylation of α‐Acyloxyketones by C(sp ³ )−O Bond Cleavage
  作者：Ryohei Doi、Akimasa Yabuta、Yoshihiro Sato

  DOI：10.1002/chem.201900582

  日期：2019.4.23

  Palladium‐catalyzed decarboxylative alkynylation of α‐acyloxyketones triggered by C(sp3)−O bond cleavage is disclosed. The decarboxylation strategy featuring a neutral reaction condition enabled an unprecedent catalytic alkynylation of a ketone enolate. The reaction was applied to a variety of substrates, giving desired products in good yields. We successfully obtained X‐ray crystallography of a new

  公开了由C（sp 3）-O键断裂引发的钯催化的α-酰氧基酮的脱羧烷基化反应。具有中性反应条件的脱羧策略可以使酮烯醇酸酯发生前所未有的催化炔基化反应。该反应被应用于多种底物，以高收率得到期望的产物。我们成功地通过[Pd（cod）（CH 2 TMS）2 ]与XPhos和α-酰氧基酮在室温下的反应合成了一种新的钯-烯酸酯中间体的X射线晶体学，表明C（sp 3）很容易−O键断开。
• Novel Tricyclic Compounds
  申请人：Wishart Neil

  公开号：US20090312338A1

  公开（公告）日：2009-12-17

  The invention provides a compound of Formula (I) pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variable are defined herein. The compounds of the invention are useful for treating immunological and oncological conditions.

  这项发明提供了一个符合Formula (I)的化合物，其中包括药用盐、前药、生物活性代谢物、立体异构体和同分异构体，其中变量在此处定义。该发明的化合物对治疗免疫和肿瘤疾病有用。
• Facile and efficient preparation of α-halomethyl ketones from α-diazo ketones catalyzed by iron(III) halides and silica gel
  作者：Xinxia Shi、Lingqiong Zhang、Pengfei Yang、Han Sun、Yilan Zhang、Chunsong Xie、Zhen Ou-yang、Min Wang

  DOI：10.1016/j.tetlet.2018.02.024

  日期：2018.3

  An efficient and mild method for the synthesis of α-halomethyl ketones from α-diazo ketones was developed using ferric chloride or bromide as the halogen source and silica gel as the hydrogen source, with good to excellent yields.

  以氯化铁或溴​​化物为卤素源，硅胶为氢源，开发了一种由α-重氮酮合成α-卤代甲基酮的高效温和方法。
• First Catalyzed Hydration of Halo­alkynes by a Recyclable Catalytic ­System
  作者：Huaxu Zou、Weibao He、Qizhi Dong、Ruijia Wang、Niannian Yi、Jun Jiang、Dongming Pen、Weimin He

  DOI：10.1002/ejoc.201501198

  日期：2016.1

  The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also

  基于 Cu(OAc)2 催化剂和 TFA（三氟乙酸）促进剂的组合，卤代炔烃水合生成 α-卤代甲基酮。这是首次通过可回收催化系统催化的水合反应合成氯/溴/碘甲基酮。该催化体系具有广泛的底物范围和优异的化学选择性，并且该程序还可以按比例放大。