对叔丁基苯基环丙基甲酮 | 38675-79-5

• 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 - 有机氧化合物
• 中文名称: 对叔丁基苯基环丙基甲酮
• 中文别名: 4-叔丁基苯基环丙基甲基酮
• 英文名称: (4-(tert-butyl)phenyl)(cyclopropyl)methanone
• 英文别名: 4-tert-Butylphenyl cyclopropyl ketone；(4-tert-butylphenyl)-cyclopropylmethanone
• CAS: 38675-79-5
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: XVDLXILLBPXUPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  56-60 °C
• 沸点：
  303.6±21.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2914399090
• 储存条件：
  请将密闭保存在阴凉干燥的环境中。

SDS

Name:	Cyclopropyl [4-(1 1-Dimethylethyl)Phenyl]- Methanone Material Safety Data Sheet
Synonym:	None
CAS:	38675-79-5

Section 1 - Chemical Product MSDS Name:Cyclopropyl [4-(1 1-Dimethylethyl)Phenyl]- Methanone Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
38675-79-5	Cyclopropyl [4-(1,1-Dimethylethyl)Phen	ca 100	254-078-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 38675-79-5: 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:
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: Not available.
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: C14H18O
Molecular Weight: 202.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 38675-79-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cyclopropyl [4-(1,1-Dimethylethyl)Phenyl]- Methanone - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 38675-79-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 38675-79-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 38675-79-5 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：

  对叔丁基苯基环丙基甲酮 在 sodium hexamethyldisilazane 、 三苯碳四(五氟苯基)硼酸盐 作用下， 以 四氢呋喃 、 氯苯 为溶剂， 反应 0.67h， 生成 4-(4-(tert-butyl)phenyl)-1,1-diethylsilinane
  参考文献：
  名称：

  芳基取代的乙烯基环丙烷和涉及芳基迁移的氢硅烷的硅离子促进的（5 + 1）环加成反应。

  摘要：

  据报道，芳基取代的乙烯基环丙烷（VCP）和氢硅烷可进行无过渡金属（5 + 1）环加成反应，得到硅环己烷。催化量的三苯甲基阳离子通过从氢化硅烷中夺取氢化物来引发反应，并通过硅离子的自我再生来保持反应的进一步进展。新的反应涉及芳基的[1,2]迁移，最终提供4取代3取代的芳基硅烷环己烷衍生物作为主要产物。各种控制实验和量子化学计算都支持了一种机理图，其中通过环丙烷环分子内稳定的甲硅烷基离子可以进行动力学上有利的协同[1,2]芳基迁移/环扩展或参与环丙烷-环丙烷重排。

  DOI：

  10.1002/anie.202004320
• 作为产物：
  描述：

  4-叔丁基苯基溴化镁 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 对叔丁基苯基环丙基甲酮
  参考文献：
  名称：

  通过高价碘氧化环丁醇向环丙基酮的轻度环收缩

  摘要：

  已经开发出碘介导的环丁醇的氧化环收缩。该反应可以在温和且环保的条件下合成各种芳基环丙基酮。反应中可以很好地耐受各种官能团，包括芳族或烷基卤化物，醚，酯，酮，烯烃，甚至醛。这与传统的合成方法相反，在传统的合成方法中，官能团的耐受性通常很差。碘氧化系统的可调性也突出了该方法的实用性。具体而言，将碘（III）试剂与适当的碱结合使用可使反应适应一系列富挑战性的富电子芳烃底物。在此也显示了该反应的简便可扩展性。

  DOI：

  10.1002/adsc.201701237

文献信息

• Copper−Carbene Complexes as Catalysts in the Synthesis of Functionalized Styrenes and Aliphatic Alkenes
  作者：Hélène Lebel、Michaël Davi、Silvia Díez-González、Steven P. Nolan

  DOI：10.1021/jo061781a

  日期：2007.1.1

  2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.

  （NHC）-Cu（NHC = N-杂环卡宾）配合物在三甲基甲硅烷基重氮甲烷，三苯基膦和2-丙醇的存在下有效催化了各种脂肪族和芳香族醛和酮的甲基化反应。与铑配合物相比，铜催化剂不仅价格便宜，而且与芳族醛和酮的官能团相容性也更好。实际上，对于形成含有硝基，三氟甲基，氨基和酯基的苯乙烯，以及吡啶，吡咯和吲哚取代的烯烃，都获得了很高的产率。
• Palladium-Catalyzed Carbonylative Cross-Coupling Reaction between Aryl(Heteroaryl) Iodides and Tricyclopropylbismuth: Expedient Access to Aryl Cyclopropylketones
  作者：Emeline Benoit、Julien Dansereau、Alexandre Gagnon

  DOI：10.1055/s-0036-1590832

  日期：2017.12

  The carbonylative cross-coupling reaction between aryl and heteroaryl iodides and tricyclopropylbismuth is reported. The reaction is catalyzed by (SIPr)Pd(allyl)Cl, a NHC-palladium(II) catalyst, operates under 1 atm of carbon monoxide and tolerates a wide range of functional groups. The use of lithium chloride was found to provide higher yields of the desired aryl cyclopropylketones. The conditions

  报道了芳基和杂芳基碘化物与三环丙基铋之间的羰基化交叉偶联反应。该反应由 (SIPr)Pd(烯丙基)Cl 催化，这是一种 NHC-钯 (II) 催化剂，在 1 个大气压的一氧化碳下运行，并能耐受多种官能团。发现使用氯化锂可提供更高产率的所需芳基环丙基酮。该条件也适用于碘代烯烃的羰基化交叉偶联，以提供相应的烯基环丙基酮。
• Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines
  作者：Julia R. Dorsheimer、Melissa A. Ashley、Tomislav Rovis

  DOI：10.1021/jacs.1c10150

  日期：2021.11.24

  activate α-3° amines for deaminative arylation via condensation with an electron-rich aldehyde and merge this reactivity with nickel metallaphotoredox to generate benzylic quaternary centers, a common motif in pharmaceuticals and natural products. The reaction is accelerated by added ammonium salts. Evidence is provided in support of two roles for the additive: inhibition of nickel black formation and acceleration

  我们报告了一种通过与富电子醛缩合来激活 α-3° 胺以进行脱氨芳基化的方法，并将这种反应性与镍金属光氧化还原结合以生成苄基季铵中心，这是药物和天然产物中的常见基序。加入铵盐可加速反应。提供的证据支持添加剂的两个作用：抑制镍黑形成和加速总反应速率。我们展示了广泛的胺和卤代芳烃偶联伙伴，并展示了 ALK2 抑制剂的加速合成。
• B(C₆F₅)₃-Catalyzed Hydrosilylation of Vinylcyclopropanes
  作者：Peng-Wei Long、Tao He、Martin Oestreich

  DOI：10.1021/acs.orglett.0c02751

  日期：2020.9.18

  reported. For the majority of VCPs, little or no ring opening of the cyclopropyl unit is observed. Conversely, for VCPs with bulky R groups, such as ortho-substituted aryl rings or branched alkyl residues, ring opening is the exclusive reaction pathway. This finding is explained by the thwarted hydride delivery to a sterically shielded, β-silicon-stabilized cyclopropylcarbinyl cation intermediate.

  据报道，强硼路易斯酸B（C 6 F 5）3催化乙烯基环丙烷（VCP）的硅氢化。对于大多数VCP，观察到很少或没有环丙基单元的开环。相反，对于具有庞大R基团的VCP，例如邻位取代的芳基环或支链烷基残基，开环是唯一的反应途径。这一发现可以通过阻止氢化物向空间屏蔽的，β-硅稳定的环丙基羰基阳离子中间物的传递来解释。
• Samarium Diiodide Induced Reactions of Cyclopropyl Ketones: Reductive Ring Cleavage and Dimerization Leading to 1,8-Diketones – Scope, Limitations, Mechanisms
  作者：Francesca Aulenta、Alexandra Hölemann、Hans-Ulrich Reißig

  DOI：10.1002/ejoc.200500945

  日期：2006.4

  cleaved, whereas the second one is still present. The reductive dimerization of cyclopropyl 2-thienyl ketone (21) furnished the product 22, which still contains two cyclopropyl groups. Further examples demonstrate the diversity of samarium diiodide induced reductions of cyclopropyl ketones. Plausible reaction mechanisms involving samarium ketyl intermediates are presented.(© Wiley-VCH Verlag GmbH & Co

  二碘化钐/HMPA 复合物与烷基环丙基酮如 3、5 和 7 的反应提供了包含 1,8-二酮部分的二聚体。产物 4、6 和 8 以中等至良好的产率分离。芳基取代的环丙基酮提供了更广泛的产物谱，这是由于钐中间体对芳基的攻击。环丙基苯基酮 (13) 得到二聚体 14，其中一个环丙烷环被还原裂解，而第二个环仍然存在。环丙基 2-噻吩基酮 (21) 的还原二聚得到产物 22，其仍含有两个环丙基。进一步的例子证明了二碘化钐诱导环丙基酮还原的多样性。介绍了涉及钐羰基中间体的合理反应机制。