(R)-3-苯基环己酮 | 34993-51-6

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-3-苯基环己酮
• 英文名称: (R)-3-phenylcyclohexanone
• 英文别名: 3-phenylcyclohexanone；(R)-3-phenylcyclohexan-1-one；3-phenylcyclohexan-1-one；(3R)-3-phenylcyclohexan-1-one
• CAS: 34993-51-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: CJAUDSQXFVZPTO-LLVKDONJSA-N

物化性质

• 沸点：
  100-102 °C(Press: 0.1 Torr)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

SDS

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Section I.Chemical Product and Company Identification
Chemical Name (R)-3-Phenylcyclohexanone
Portland OR
Not available.
Synonym
C12H14O
Chemical Formula
CAS Number 34993-51-6

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
(R)-3-Phenylcyclohexanone 34993-51-6 Min. 97.0 Not available. Not available.
(GC)

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the
toxic material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Not available.
Auto-Ignition
Flammability May be combustible at high temperature.
Flash Points Flammable Limits Not available.
Not available.
Combustion Products These products are toxic carbon oxides (CO, CO2).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
(R)-3-Phenylcyclohexanone

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Section VI. Accidental Release Measures
Spill Cleanup If the product is in its solid form: Use a shovel to put the material into a convenient waste disposal container. If the
product is in its liquid form: Absorb with an inert material and put the spilled material in an appropriate waste disposal.
Instructions
Finish cleaning the spill by rinsing any contaminated surfaces with copious amounts of water. Consult federal, state,
and/or local authorities for assistance on disposal.

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Section VII. Handling and Storage
Handling and Storage REFRIGERATE. Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and
store in a dry, cool place. Avoid excessive heat and light. Do not breathe gas/fumes/ vapor/spray.
Information
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors below their
respective threshold limit value. Ensure that eyewash station and safety shower is proximal to the work-station location.
Personal Protection Splash goggles. Lab coat. Vapor respirator. Boots. Gloves. Suggested protective clothing might not be sufficient;
consult a specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solubility
Physical state @ 20°C Liquid. (Colorless-Yellow Clear.) Not available.
1.05 (water=1)
Specific Gravity
Molecular Weight 174.24 Partition Coefficient Not available.
Boiling Point Not available. Vapor Pressure Not available.
Melting Point 19°C (66.2°F) (Freezing Point) Vapor Density Not available.
Not available. Volatility Not available.
Refractive Index
Critical Temperature Not available. Odor Not available.
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
Not available.
RTECS Number
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Toxicity Data Not available.
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Continued on Next Page
(R)-3-Phenylcyclohexanone

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Section XII. Ecological Information
Ecotoxicity Not available.
Not available.
Environmental Fate

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
DOT Classification Not a DOT controlled material (United States).
Not applicable.
PIN Number
Proper Shipping Name
Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not available.
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-3-苯基环己酮 在 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 1.0h， 生成 (1R,3R)-3-phenyl-cyclohexanecarboxylic acid amide
  参考文献：
  名称：

  [EN] NEW CCR2 ANTAGONISTS
  [FR] NOUVEAUX ANTAGONISTES DU CCR2

  摘要：

  本发明涉及一种新的CCR2（CC趋化因子受体2）拮抗剂，其化学式为（Ia），并且它们的用途是提供治疗疾病的药物，特别是肺部疾病，如哮喘和慢性阻塞性肺疾病。

  公开号：

  WO2011151251A1
• 作为产物：
  描述：

  苯基三氟甲烷磺酸酯 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 [RhCl((R,R)-Ph-bicyclo[2.2.2]octa-2,5-diene)]₂ 、 N,N-二异丙基乙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (R)-3-苯基环己酮
  参考文献：
  名称：

  通过镍和铑催化的顺序中继反应将芳基卤化物和三氟甲磺酸酯的对映选择性共轭加成至电子缺陷型烯烃。

  摘要：

  通过在一个锅中依次进行Miyaura硼化和Hayashi-Miyaura共轭添加，可以将芳基卤化物或芳基三氟甲磺酸酯不对称共轭添加到缺电子烯烃中。镍催化的芳基卤化物或三氟甲磺酸酯的硼酸酯化和铑-手性二烯配合物催化的对映选择性共轭物的添加作为一对中继反应进行，是一种更有效，更环保的方案。

  DOI：

  10.1021/acs.orglett.9b02940

文献信息

• Synthesis, Characterization, and Application of Segphos Derivative Having Diferrocenylphosphino-Donor Moieties
  作者：Hao Hu、Hiroki Ichiryu、Naoki Seki、Kiyohiko Nakajima、Yasuhiro Ohki、Masamichi Ogasawara

  DOI：10.1021/acs.organomet.9b00865

  日期：2020.3.23

  coordinated to a palladium(II) cation in a bidentate fashion to construct a unique chiral environment at the palladium center due to the sterically demanding ferrocenyl groups. Ligand (R)-1 was applied in the palladium-catalyzed asymmetric synthesis of axially chiral allenes showing good enantioselectivity of up to 92% ee. In general, (R)-1 displayed better enantioselectivity than the parent Segphos in the

  制备具有二铁茂铁基膦酰基供体部分的轴向手性双膦，Fc-Segphos（1），作为外消旋体，并且其光学拆分通过使用手性HPLC来实现。由于空间上需要二茂铁基，配体1以二齿形式与钯（II）阳离子配位以在钯中心构建独特的手性环境。配体（R）-1用于钯催化的轴向手性异戊烯的不对称合成，显示出高达92％ee的良好对映选择性。通常，在钯催化的反应中，（R）-1显示出比母体Segphos更好的对映选择性，而Pd /（R）-与（R）-Segphos衍生的钯催化剂相比，有1个种类的ee增强了18％。
• Low‐Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands
  作者：Durga Prasad Hari、Guillaume Pisella、Matthew D. Wodrich、Artem V. Tsymbal、Farzaneh Fadaei Tirani、Rosario Scopelliti、Jerome Waser

  DOI：10.1002/anie.202012299

  日期：2021.3

  The intramolecular [4+2] cycloaddition between arenes and allenes first reported by Himbert gives rapid access to rigid polycyclic scaffolds. Herein, we report a one‐pot oxyalkynylation/cycloaddition reaction proceeding under mild conditions (23–90 °C) and providing complex polycyclic architectures with high efficiency, and atom and step economy. The bicyclo[2.2.2]octadiene products were obtained with

  辛伯特（Himbert）首次报道，在芳烃和丙二烯之间进行分子内[4 + 2]环加成反应，可以快速获得刚性多环支架。本文中，我们报告了在温和条件下（23–90°C）进行的单锅氧基炔基化/环加成反应，并提供了高效，原子和步骤经济的复杂多环结构。获得具有多种有用官能团的双环[2.2.2]辛二烯产物，并成功地用作金属催化的手性配体。计算研究基于过渡状态中反直觉的有利色散相互作用，首次合理地给出了环加成反应的低活化能。
• Design and Synthesis of Polymeric Chiral Bicyclo[3.3.0] Diene as Reusable Ligand for Rhodium-Catalyzed Asymmetric 1,4-Addition
  作者：Hongyu Yang、Minghua Xu

  DOI：10.1002/cjoc.201201079

  日期：2013.1

  A series of A‐B type sterically regular bicyclio[3.3.0] diene‐based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. With polymeric diene 6b, good to excellent enantioselectivities can be achieved in Rh‐catalyzed asymmetric 1,4‐addition of arylboronic acids to α,β‐unsaturated ketones.

  设计并合成了一系列基于A‐B型空间正则双环[3.3.0]二烯的聚合物，作为固定的手性二烯配体进行不对称催化。使用聚合二烯6b，可以在Rh催化的芳基硼酸的不对称1,4-加成反应中获得出色的对映选择性，对α，β-不饱和酮。
• Asymmetric syntheses of 3-substituted-cyclohexanone derivatives by stereoselective conjugate addition to chiral 2-substituted-2-cyclohexen-1-ones
  作者：Arthur G. Schultz、Roger E. Harrington

  DOI：10.1021/ja00013a031

  日期：1991.6

  Chiral 2-substituted-2-cyclohexen-1-one 2a is prepared. Conjugate additions of organometallic reagents to 2a occur with good to excellent diastereoselectivities. Enone 2b, which contains an additional potentially coordinating oxygen atom on the side chain of the chiral auxiliary, gave about the same stereoselectivity as 2a. The chiral auxiliary (S)-(+)-2-(methoxymethyl)pyrrolidine can be removed from

  制备手性2-取代-2-环己烯-1-酮2a。有机金属试剂与 2a 的共轭加成具有良好到极好的非对映选择性。Enone 2b 在手性助剂的侧链上包含一个额外的潜在配位氧原子，其立体选择性与 2a 大致相同。手性助剂 (S)-(+)-2-(甲氧基甲基)吡咯烷可通过在 60°C 下用盐酸羟胺和醋酸钠在 95% 乙醇中处理从缀合物加成产物中去除，得到 3-取代环己酮
• Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors
  作者：Jeffrey C. Holder、Alexander N. Marziale、Michele Gatti、Bin Mao、Brian M. Stoltz

  DOI：10.1002/chem.201203643

  日期：2013.1.2

  Flava Flavanone: Asymmetric conjugate additions to chromones and 4‐quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF3)2 and (S)‐tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).

  Flava 黄烷酮：据报道，使用由 Pd(OCOCF 3 ) 2和 ( S ) -t BuPyOX原位形成的单一催化剂体系，不对称共轭加成到色酮和 4-喹诺酮。值得注意的是，这些反应是在环境气氛下在湿溶剂中进行的，并使用容易获得的芳基硼酸作为亲核试剂，从而提供了对这些不对称杂环的快速访问（参见方案）。