1-[2-羟基-6-(异戊基氧基)苯基]-1-乙酮 | 249278-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[2-羟基-6-(异戊基氧基)苯基]-1-乙酮
• 英文名称: 1-(2-hydroxy-6-(isopentyloxy)phenyl)ethanone
• 英文别名: 1-[2-hydroxy-6-(3-methylbutoxy)phenyl]ethanone
• CAS: 249278-25-9
• 化学式: C₁₃H₁₈O₃
• mdl: MFCD00100622
• 分子量: 222.284
• InChiKey: KFBRVHJODGMLFK-UHFFFAOYSA-N

物化性质

• 熔点：
  25-27°C
• 沸点：
  328.0±22.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38

SDS

Name:	1-[2-Hydroxy-6-(isopentyloxy)phenyl]ethan-1-one 97% Material Safety Data Sheet
Synonym:
CAS:	249278-25-9

Section 1 - Chemical Product MSDS Name:1-[2-Hydroxy-6-(isopentyloxy)phenyl]ethan-1-one 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
249278-25-9	1-[2-Hydroxy-6-(isopentyloxy)phenyl]et	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
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:
Not available.

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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.
Ingestion:
Get medical aid. 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.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 249278-25-9: Personal Protective Equipment Eyes: Not available.
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: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 25 - 27 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:
Specific Gravity/Density:
Molecular Formula: C13H18O3
Molecular Weight: 222

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acid chlorides.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 249278-25-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-[2-Hydroxy-6-(isopentyloxy)phenyl]ethan-1-one - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 249278-25-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 249278-25-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 249278-25-9 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：

  1-[2-羟基-6-(异戊基氧基)苯基]-1-乙酮 在 sodium tetrahydroborate 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.67h， 生成 phenyl 2-hydroxyethyl((5-(isopentyloxy)-4-oxo-4H-chromen-3-yl)methyl)carbamate
  参考文献：
  名称：

  N-酰基羟乙基氨基甲基-4 H - chromen-4 -one支架的新型类似物作为IL-5抑制剂

  摘要：

  制备了许多N-酰基取代的羟乙基氨基甲基-4 H-铬基-4-酮6a – u并评估了其对IL-5的抑制活性。其中，化合物6r（在30 µM时抑制率为95.0％，IC 50  = 10.0 µM，C log P = 4.1549）显示出最有效的抑制活性。结构活性关系表明，尿素，氨基甲酸酯或酰胺基团上较大或疏水的取代基对IL-5具有良好的抑制活性。此外，苯环上的给电子基团（6g和6s）比吸电子基团（6f）更具活性）。最后，用大的脂族取代基取代环A第5位的环己基甲氧基导致活性丧失。

  DOI：

  10.1016/j.bmc.2017.06.018
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 、 1-溴代异戊烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.0h， 以70%的产率得到1-[2-羟基-6-(异戊基氧基)苯基]-1-乙酮
  参考文献：
  名称：

  发现新的3-（羟基烷氧基）-2-烷基铬-4-酮类似物作为白介素5抑制剂

  摘要：

  设计，合成并评估了一系列新颖的chromen-4-one类似物9a-d和10a-u，并评估了它们对IL-5的抑制活性。大多数chromen-4-one类似物在低微摩尔效价下显示出强大的抑制活性。其中，5-（环己基甲氧基）-3-（3-羟基丙氧基）-2-异丙基-4 H- 铬-4--4-酮（10t，在30μM时抑制率为90.0％，IC 50 = 5.5μM，CLogP = 4.76887）和2-cyclohexyl-5-（cyclohexylmethoxy）-3-（3-hydroxypropoxy）-4 H -chromen-4-one（10u，在30μM下的抑制率为95.5％，IC 50 = 3.0μM，CLogP = 5.96187）表现出最好的抑制作用。结构活性关系表明，在色环-4-1环A的5位上的疏水环己基甲氧基比在位置6更优选，并且在色环-4-1环上的双氢键键合受体性质对于抑制具有重要

  DOI：

  10.1016/j.ejmech.2017.07.069

文献信息

• Synthesis and evaluation of novel chromone analogs for their inhibitory activity against interleukin-5
  作者：Pillaiyar Thanigaimalai、Tuan Anh Le Hoang、Ki-Cheul Lee、Vinay K. Sharma、Seong-Cheol Bang、Jun Ho Yun、Eunmiri Roh、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2010.02.041

  日期：2010.6

  A novel series of chromone analogs were synthesized and evaluated for their inhibitory activity against interleukin-5. Among them compounds 5-Cyclohexylmethoxy-3-(4-hydroxybenzyl)-4H-chromen-4-one (6a, 98% inhibition at 30 μM, IC50 < 3.0 μM) and 5-Cyclohyxylmethoxy-3-(hydroxymethyl)-4H-chromen-4-one (8a, 84% inhibition at 30 μM, IC50 = 7.6 μM) showed most potent activity. The structural requirement

  合成了一系列新的色酮类似物，并评估了其对白介素5的抑制活性。其中化合物5-环己基甲氧基-3-（4-羟基苄基）-4 H- 铬-4--4-酮（6a，在30μM时抑制率为98％，IC 50 <3.0μM）和5-环己基甲氧基-3-（羟甲基）- 4 H -chromen-4-one（8a，30μM时抑制84％，IC 50 = 7.6μM）表现出最强的活性。具有抑制IL-5抑制活性的色酮类似物的结构要求可以概括为：（i）疏水基团（在环A的第5位的环己基甲氧基）的重要性，（ii）具有较小氢键基团的环B的要求具有给电子性，例如在第4位的酚羟基和（iii）1-4n铬烯环的平面性。
• Anti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells
  作者：Eeda Venkateswararao、Vinay K. Sharma、Jieun Yun、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmc.2014.04.045

  日期：2014.7

  To investigate the anti-proliferative effect of NF-kappa B inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5a) were prepared and evaluated for their NE-kappa B inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5e) and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide (5p) showed good NF-kappa B inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-kappa B inhibition displayed good anti-proliferative activity. All the analogs (5b-r) maintained a good correlation between their NE-kappa B inhibition and anti-proliferative activity though the extent is not directly proportional to each other. (C) 2014 Elsevier Ltd. All rights reserved.
• Novel analogs of N-acylhydroxyethylaminomethyl-4H-chromen-4-one scaffold as IL-5 inhibitors
  作者：Hyun-Sun Yang、Eeda Venkateswararao、Pulla Reddy Boggu、Vinay K. Sharma、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmc.2017.06.018

  日期：2017.8

  A number of N-acyl substituted hydroxyethylaminomethyl-4H-chromen-4-ones 6a–u were prepared and evaluated for their IL-5 inhibitory activity. Among them, the compound 6r (95.0% inhibition at 30 µM, IC50 = 10.0 µM, C log P = 4.1549) showed most potent inhibitory activity. The structure activity relationship revealed that the bulkier or hydrophobic substituents at urea, carbamate or amide group resulted

  制备了许多N-酰基取代的羟乙基氨基甲基-4 H-铬基-4-酮6a – u并评估了其对IL-5的抑制活性。其中，化合物6r（在30 µM时抑制率为95.0％，IC 50  = 10.0 µM，C log P = 4.1549）显示出最有效的抑制活性。结构活性关系表明，尿素，氨基甲酸酯或酰胺基团上较大或疏水的取代基对IL-5具有良好的抑制活性。此外，苯环上的给电子基团（6g和6s）比吸电子基团（6f）更具活性）。最后，用大的脂族取代基取代环A第5位的环己基甲氧基导致活性丧失。
• Discovery of novel 3-(hydroxyalkoxy)-2-alkylchromen-4-one analogs as interleukin-5 inhibitors
  作者：Pulla Reddy Boggu、Eeda Venkateswararao、Manoj Manickam、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2017.07.069

  日期：2017.10

  the hydrophobic cyclohexylmethoxy group at the position 5 of the chromen-4-one ring A is preferable than at position 6 and the dual hydrogen bonding acceptor property on the chromen-4-one ring should be important for the inhibitory activity. In addition, the optimum length of the side chain at position 3 of chromen-4-one ring is critical for the donation of hydrogen to the binding site and the 3-hydroxypropoxy

  设计，合成并评估了一系列新颖的chromen-4-one类似物9a-d和10a-u，并评估了它们对IL-5的抑制活性。大多数chromen-4-one类似物在低微摩尔效价下显示出强大的抑制活性。其中，5-（环己基甲氧基）-3-（3-羟基丙氧基）-2-异丙基-4 H- 铬-4--4-酮（10t，在30μM时抑制率为90.0％，IC 50 = 5.5μM，CLogP = 4.76887）和2-cyclohexyl-5-（cyclohexylmethoxy）-3-（3-hydroxypropoxy）-4 H -chromen-4-one（10u，在30μM下的抑制率为95.5％，IC 50 = 3.0μM，CLogP = 5.96187）表现出最好的抑制作用。结构活性关系表明，在色环-4-1环A的5位上的疏水环己基甲氧基比在位置6更优选，并且在色环-4-1环上的双氢键键合受体性质对于抑制具有重要