1-(2-羟基-5-甲基)-3-苯基-1,3-丙烷二酮 | 29976-82-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-(2-羟基-5-甲基)-3-苯基-1,3-丙烷二酮
• 中文别名: 1-(2-羟基-5-甲基苯基)-3-苯基-1,3-丙二酮
• 英文名称: 1-(2-hydroxy-5-methylphenyl)-3-phenylpropane-1,3-dione
• 英文别名: 1-(2-hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione
• CAS: 29976-82-7
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: OKAQJPKEOQHKKY-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C(lit.)
• 沸点：
  437.3±35.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在室温下，应保持干燥并密封。

SDS

Name:	1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1 3-propanedione Material Safety Data Sheet
Synonym:	None Known
CAS:	29976-82-7

Section 1 - Chemical Product MSDS Name:1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1 3-propanedione Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
29976-82-7	1-(2-Hydroxy-5-methylphenyl)-3-phenyl-	97	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

---

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. Wash mouth out with 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:
Treat symptomatically and supportively.

---

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 water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 29976-82-7: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 92 - 94 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C16H14O3
Molecular Weight: 254.59

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 29976-82-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 29976-82-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 29976-82-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 29976-82-7 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-(2-羟基-5-甲基)-3-苯基-1,3-丙烷二酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 生成 6-bromomethylflavone
  参考文献：
  名称：

  黄酮类化合物作为有效抗癌药的替代作用研究：结构-活性关系研究

  摘要：

  设计并合成了三个系列的类黄酮类似物，这些类黄酮类似物在C-6，C-7和C-8处被不同的氨甲基取代，作为有效的抗癌药进行结构-活性关系研究。评价了制备的类似物对肝癌细胞HepG2和SMMC-7721生长的体外抑制活性。结构-活性关系表明，不仅具有氨基甲基的化合物比没有相同系列基团的化合物更具活性，而且在C-8位被氨基甲基取代的化合物比在C-6和C-6位的化合物更具活性。 C-7。

  DOI：

  10.1007/s00044-011-9701-6
• 作为产物：
  描述：

  乙酸对甲酚酯 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 1-(2-羟基-5-甲基)-3-苯基-1,3-丙烷二酮
  参考文献：
  名称：

  黄酮类化合物作为有效抗癌药的替代作用研究：结构-活性关系研究

  摘要：

  设计并合成了三个系列的类黄酮类似物，这些类黄酮类似物在C-6，C-7和C-8处被不同的氨甲基取代，作为有效的抗癌药进行结构-活性关系研究。评价了制备的类似物对肝癌细胞HepG2和SMMC-7721生长的体外抑制活性。结构-活性关系表明，不仅具有氨基甲基的化合物比没有相同系列基团的化合物更具活性，而且在C-8位被氨基甲基取代的化合物比在C-6和C-6位的化合物更具活性。 C-7。

  DOI：

  10.1007/s00044-011-9701-6

文献信息

• Synthesis of novel fused chromone–pyrimidine hybrids and 2,4,5-trisubstituted pyrimidine derivatives via ANRORC rearrangement
  作者：M. Sambaiah、K. Raghavulu、K. Shiva Kumar、Satyanarayana Yennam、Manoranjan Behera

  DOI：10.1039/c7nj01839h

  日期：——

  A facile and versatile procedure for the synthesis of functionalized novel 2, 5-diphenyl-5H-chromeno [4, 3-d] pyrimidin-5-ol and (2, 4-diphenylpyrimidin-5-yl) (2-hydroxyphenyl) methanone has been described. The key step in the synthesis involves the ANRORC reaction of 3-benzoyl chromones with benzamidines.

  一种简便且通用的方法，用于合成功能化的新型2，5-二苯基-5H-铬[4，3-d]嘧啶-5-醇和（2，4-二苯基嘧啶-5-基）（2-羟苯基）甲酮已经描述过了。合成中的关键步骤涉及3-苯甲酰色酮与苯甲the的ANRORC反应。
• Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABA_A Receptor
  作者：Pia Kahnberg、Erik Lager、Celia Rosenberg、Jette Schougaard、Linda Camet、Olov Sterner、Elsebet Østergaard Nielsen、Mogens Nielsen、Tommy Liljefors

  DOI：10.1021/jm020839k

  日期：2002.9.1

  develop and evaluate a pharmacophore model previously proposed by Cook and co-workers (Drug Des. Discovery 1995, 12, 193-248) for ligands binding to the benzodiazepine site of the GABA(A) receptor, 40 new flavone derivatives have been synthesized and their affinities for the benzodiazepine site have been determined. Two new regions of steric repulsive interactions between ligand and receptor have been

  为了进一步开发和评估以前由Cook和他的同事提出的药效团模型（Drug Des.Discovery 1995，12，193-248），其用于与GABA（A）受体的苯二氮杂位点结合的配体，已经开发了40种新的黄酮衍生物。已经确定了它们的合成及其对苯并二氮杂site位点的亲和力。表征了配体和受体之间的两个空间排斥相互作用的新区域，并且已绘制出6-和3'-取代基附近的受体区域。显示了2'-羟基取代使亲和力显着增加，这是根据与先前提出的氢键接受位点A2的新型氢键相互作用来解释的。根据这些研究的结果和改进的药效团模型，5'-溴-2'-羟基-6-甲基黄酮，成功设计了迄今为止报道的最高亲和力的黄酮衍生物（K（i）= 0.9 nM）。已经比较了药效团模型与最近提出的替代模型（Marder；等人，Bioorg。Med。Chem。，2001，9，323-335）。
• New Synthesis of 3-Bromoflavones via Bromination of 1-(2-Hydroxyphenyl)-3-arylpropane-1,3-dione by CuBr₂, and Conversion into 3-Aminoflavones
  作者：Hideyoshi Miyake、Shouko Nishino、Akinori Nishimura、Mitsuru Sasaki

  DOI：10.1246/cl.2007.522

  日期：2007.4.5

  A new synthesis of 3-bromoflavones from 1-(2-hydroxyphenyl)-3-arylpropane-1,3-dione using CuBr2 is described. The usefulness of 3-bromoflavone as a precursor of 3-aminoflavone is also described.

  描述了一种使用CuBr2从1-(2-羟基苯基)-3-芳基丙烯-1,3-二酮合成3-溴黄酮的新方法。此外，3-溴黄酮作为3-氨基黄酮前体的有用性也进行了描述。
• A very simple solvent-free method for the synthesis of 2-arylchromones using KHSO4 as a recyclable catalyst
  作者：María Pérez、Diego Ruiz、Juan Autino、Angel Sathicq、Gustavo Romanelli

  DOI：10.1016/j.crci.2016.02.014

  日期：2016.5

  Résumé An efficient and solvent-free procedure for the synthesis of flavones using KHSO4 as a recyclable catalyst is described. The methodology represents an environmentally friendly process in comprehensive consideration compared with other catalytic systems listed in publications. This method provides a clean, simple, solvent-free reaction and useful alternatives to prepare flavones and chromones. The use of KHSO4 catalyst provides excellent yields, also leading to an easy separation and recovery of the catalysts, which allows both low environmental impact and low cost. Other green advantages of the method are the low formation of wastes and the replacement of corrosive, soluble mineral acids. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  摘要 本文描述了一种高效无溶剂的黄酮合成程序，采用KHSO4作为可回收催化剂。这种方法在综合考虑下，与其他文献中列出的催化系统相比，代表了一种环保的过程。该方法提供了一种清洁、简单、无溶剂的反应，并为制备黄酮和色酮提供了有用的替代方案。使用KHSO4催化剂可实现优异的产率，同时便于催化剂的分离和回收，这不仅降低了环境影响，还降低了成本。该方法的其他绿色优势包括废物生成少，以及替代腐蚀性可溶性矿酸。 补充材料： 本文章的补充材料作为单独文件提供：mmc1.doc
• Benzopyrans. Part 41. Reactions of 2-(2-dimethylaminovinyl)-1-benzopyran-4-ones with various dienophiles
  作者：Chandra Kanta Ghosh、Samita Bhattacharyya、Chandreyi Ghosh、Amarendra Patra

  DOI：10.1039/a903145f

  日期：——

  propiolate (EP) ultimately gives xanthenones 33, 34 and 37, respectively, the latter being admixed with flavone 43. Enamine 2, cyclisable to xanthenone 11, gives 33 and 35 with DMAD, and 37 and 44 with EP. Reaction of 3 with DMAD affords 36 exclusively.

  二烯胺1与N-苯基马来酰亚胺和色酮14以及15通过最初的[4 + 2]环加成反应分别产生黄酮酮10和18。最初对色酮14和16的迈克尔加成反应以及乙酰二羧酸二甲酯（DMAD）分别触发了氧杂酮19、4-氮杂蒽酮26和富马酸酯49的形成。二烯胺1–3与亲电子乙炔的初始[2 + 2]环加合物始终会经历进一步的转化。因此，具有DMAD的1，二苯甲酰基乙炔和丙酸乙酯（EP）最终分别产生黄酮酮33、34和37，后者与黄酮43混合。烯胺2，可环化为黄酮酮11，产生33和35的DMAD，以及37和37带EP的44。3与DMAD的反应仅得到36。