1-苯基-2-丙烯基-1-酮 | 768-03-6

• 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: 1-苯基-2-丙烯基-1-酮
• 中文别名: 苯基丙烯基酮
• 英文名称: PVK
• 英文别名: Phenyl vinyl ketone；1-phenylprop-2-en-1-one；acrylophenone；vinyl phenyl ketone；1-phenyl-2-propenyl-1-one
• CAS: 768-03-6
• 化学式: C₉H₈O
• mdl: MFCD00457275
• 分子量: 132.162
• InChiKey: KUIZKZHDMPERHR-UHFFFAOYSA-N

物化性质

• 沸点：
  204.08°C (rough estimate)
• 密度：
  1.0270 (rough estimate)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 保留指数：
  1138;1147

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H227,H302,H315,H319,H332,H335
• 储存条件：
  -20°C，保存在惰性气体中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Acrylophenone
Synonyms: 1-phenylprop-2-en-1-one

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Acrylophenone
CAS number: 768-03-6

---

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.

---

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.

---

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.

---

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.
Storage: Store in closed vessels, under −20◦C.

---

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.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H8O
Molecular weight: 132.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

3-氧化-3-苯基丙烯是一种针对活性位点的不可逆羟基硝基酮裂解酶抑制剂。该裂解酶为FAD蛋白。底物和竞争性抑制剂（如苯甲酸）能够减缓抑制剂介导的酶失活过程。

反应信息

• 作为反应物：
  描述：

  1-苯基-2-丙烯基-1-酮 在 盐酸 、 amalgamated zinc 、 sodium methylate 作用下， 生成 2-苯基吡咯烷
  参考文献：
  名称：

  Über die Umwandlung von 1,3-Amino-ketonen in 1,4-Nitro-ketone

  摘要：

  DOI：

  10.1002/ardp.19372750203
• 作为产物：
  描述：

  alpha-氯乙酰苯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到1-苯基-2-丙烯基-1-酮
  参考文献：
  名称：

  使用 Brønsted 碱/硫脲双功能催化剂对映选择性合成 2,3-二取代反式-2,3-二氢苯并呋喃†

  摘要：

  2,3-二取代的反式-2,3-二氢苯并呋喃衍生物（15个例子，高达96：4 dr，95：5 er）通过分子内迈克尔加成的非对映选择性和对映选择性合成已经使用酮-烯酮底物和双功能叔胺-硫脲催化剂。该方法扩展到包括用于合成 2,3-二取代茚满和 3,4-二取代四氢呋喃衍生物的非活化酮亲核试剂。

  DOI：

  10.1039/c6ob01326k

文献信息

• Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group
  作者：Li Yan Chan、Sunggak Kim、Taekyu Ryu、Phil Ho Lee

  DOI：10.1039/c3cc41107a

  日期：——

  A highly efficient Pd-catalyzed ortho-alkenylation is reported using a mono-phosphoric acid-directing group for the first time. This phosphoric acid-directing group is successfully utilized for the synthesis of various alkenylated products and offers a new approach to transition-metal-catalyzed C-H activation.

  首次报道了使用单磷酸定向基团的高效Pd催化的邻链烯基化反应。该磷酸导向基团已成功用于各种烯基化产物的合成，并为过渡金属催化的CH活化提供了一种新方法。
• Cyanomethyl anion transfer reagents for diastereoselective Corey–Chaykovsky cyclopropanation reactions
  作者：Renè Hommelsheim、Katharina J. Hock、Christian Schumacher、Mohanad A. Hussein、Thanh V. Nguyen、Rene M. Koenigs

  DOI：10.1039/c8cc05602a

  日期：——

  A readily available and bench-stable cyanomethyl sulfonium salt was used in highly diastereoselective Corey–Chaykovsky cyclopropanation reactions of electron-poor olefins. This efficient method provides a rapid route to access densely functionalized cyclopropyl nitriles.

  一种易于获得且稳定的氰基甲基methyl盐被用于高度非对映选择性的电子贫烯烃的Corey-Chaykovsky环丙烷化反应中。这种有效的方法提供了一种快速途径来获取致密的官能化环丙基腈。
• Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- and α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol
  作者：Xiao-Yu Zhan、Hua Zhang、Yu Dong、Jian Yang、Shuai He、Zhi-Chuan Shi、Lei Tang、Ji-Yu Wang

  DOI：10.1021/acs.joc.0c00568

  日期：2020.5.15

  The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies

  在温和的反应条件下，由B（C6F5）3催化的α，β-和α，β，γ，δ-不饱和酮的化学选择性氢化硅烷化为相应的不对称酮。将近55种底物，包括带有可还原官能团（例如炔基，烯基，氰基和芳香族杂环）的底物，以良好或优异的产率进行化学选择性氢化硅烷化。同位素标记研究表明，六氟-2-丙醇在该过程中也用作氢源。
• Mild Chemoenzymatic Oxidation of Allylic <i>sec</i>-Alcohols. Application to Biocatalytic Stereoselective Redox Isomerizations
  作者：Lía Martínez-Montero、Vicente Gotor、Vicente Gotor-Fernández、Iván Lavandera

  DOI：10.1021/acscatal.7b03293

  日期：2018.3.2

  β-unsaturated ketones. Afterward, these compounds react with different commercially available ene-reductases to afford the corresponding saturated ketones. Remarkably, in the case of trisubstituted alkenes, the bioreduction reaction occurred with high stereoselectivity. Overall, a bienzymatic one-pot two-step sequential strategy has been described with respect to the synthesis of saturated ketones starting

  在温和的反应条件下，在水性介质中设计催化氧化方法，并使用分子氧作为最终电子受体，是传统氧化转化的合适替代方法。如果在同一分子内存在其他可氧化的官能团（如烯丙醇的情况），则这些方法尤为重要。本文我们应用漆酶组成的简单化学酶促系统从云芝和2,2,6,6-四甲基自由基（TEMPO），以氧化一系列外消旋烯丙基的秒-醇转化为相应的α，β-不饱和酮。然后，这些化合物与不同的市售烯还原酶反应，得到相应的饱和酮。显着地，在三取代的烯烃的情况下，生物还原反应以高的立体选择性发生。总的来说，关于从外消旋烯丙基醇开始的饱和酮的合成，已经描述了双酶一锅两步顺序策略，因此类似于先前在文献中报道的这些衍生物的金属催化的氧化还原异构化。
• Preparation of α-Sulfonylethanone Oximes from Oxidized Hydroxylamine
  作者：Nan Liu、Ping Yin、Yue Chen、Yong Deng、Ling He

  DOI：10.1002/ejoc.201200133

  日期：2012.5

  Alkenes react with substituted N-hydroxysulfonamides and tetrabutylammonium periodate under metal catalyst free conditions to give oximes in good to high yields. The reaction proceeds in a one-pot manner, giving rise to the formation of intermolecular C–N and C–S bonds simultaneously. The method is mild, highly efficient, and convenient.

  烯烃与取代的 N-羟基磺酰胺和高碘酸四丁基铵在无金属催化剂的条件下反应，以良好或高产率得到肟。该反应以一锅法进行，同时形成分子间 C-N 和 C-S 键。该方法温和、高效、方便。