3-[3,5-双(三氟甲基)苯基]-3-氧丙酸乙酯 | 175278-02-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-[3,5-双(三氟甲基)苯基]-3-氧丙酸乙酯
• 英文名称: 3-(3,5-bis(trifluoromethyl)phenyl)-3-oxopropionic acid ethyl ester
• 英文别名: ethyl 3-(3,5-bis(trifluoromethyl)phenyl)-3-oxopropanoate；3-(3,5-bis-trifluoromethyl-phenyl)-3-oxo-propionic acid ethyl ester；ethyl 3-[3,5-bis(trifluoromethyl)phenyl]-3-oxopropanoate
• CAS: 175278-02-1
• 化学式: C₁₃H₁₀F₆O₃
• 分子量: 328.211
• InChiKey: IBRYPSPFMRZTCX-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 危险类别码：
  R20/21/22
• 海关编码：
  2918300090
• 安全说明：
  S24/25

SDS

Name:	Ethyl 3-[3 5-di(trifluoromethyl)phenyl]-3-oxopropanoate tech Material Safety Data Sheet
Synonym:	Ethyl[3,5-bis(trifluoromethyl)benzoyl]acetat
CAS:	175278-02-1

Section 1 - Chemical Product MSDS Name:Ethyl 3-[3 5-di(trifluoromethyl)phenyl]-3-oxopropanoate tech Material Safety Data Sheet
Synonym:Ethyl[3,5-bis(trifluoromethyl)benzoyl]acetat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175278-02-1	Ethyl 3-[3,5-di(trifluoromethyl)phenyl		unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 175278-02-1: 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: white - pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 80 - 82 deg C @0.4mmHg
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: C13H10F6O3
Molecular Weight: 328

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acids, bases, oxidizing agents, reducing agents, amines.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, acrid smoke and fumes, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175278-02-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 3-[3,5-di(trifluoromethyl)phenyl]-3-oxopropanoate - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 175278-02-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175278-02-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175278-02-1 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

制备方法与用途

简介

3-[3,5-双(三氟甲基)苯基]-3-氧丙酸乙酯是一种有机中间体，可通过3,5-双三氟甲基溴苯与丙二酸单乙酯钾在THF中一步反应制备得到。

制备

将30 mL微波管形瓶中的3,5-双(三氟甲基)溴苯（0.5 mmol）和丙二酸单乙酯钾（0.75 mmol）的THF（10 mL）混合物搅拌均匀，加入Pd(OAc)2（5 mol％）、Xantphos（5 mol％）、MgCl2（0.75 mmol）、Et3N（0.75 mmol）、咪唑（1 mmol），然后添加Co2(CO)8（0.15 mmol）。立即密封瓶口并在90°C微波照射下反应30分钟。将混合物用乙酸乙酯和水稀释，分离乙酸乙酯层并用硫酸钠干燥后浓缩。通过柱色谱法纯化粗产物，并使用0至5％的乙酸乙酯在己烷中的溶液得到纯净的化合物。

反应信息

• 作为反应物：
  描述：

  3-[3,5-双(三氟甲基)苯基]-3-氧丙酸乙酯 在 palladium on activated charcoal 重铬酸吡啶 、 四(三苯基膦)钯 、 氢气 、 三溴化磷 、 溶剂黄146 、 三乙胺 、 copper(I) bromide 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Diaryl substituted pyrazoles as potent CCR2 receptor antagonists

  摘要：

  We have identified and synthesized a series of diaryl substituted pyrazoles as potent antagonists of the chemokine receptor subtype 2. Structure-activity relationship studies directed toward improving the potency led to the discovery of 23 (IC50 = 6 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.060
• 作为产物：
  描述：

  3,5-双三氟甲基苯乙酮 、 碳酸二乙酯 在 sodium hydride 作用下， 以 甲苯 为溶剂， 生成 3-[3,5-双(三氟甲基)苯基]-3-氧丙酸乙酯
  参考文献：
  名称：

  铱催化的外消旋β'-酮-β-氨基酯的对映选择性和非对映选择性氢化通过动态动力学拆分

  摘要：

  报道了一种通过动态动力学拆分对α-取代的β-酮酯进行对映选择性氢化的铱/ f-二磷催化系统。期望的抗β”羟基β在中度至良好的产率（60-95％）与72-99％得到氨基酯EE秒和91：9到99：1个博士秒。该协议可以容忍各种官能团，并且可以轻松地以较低的催化剂负载量（TON 高达 9100）以克规模进行。

  DOI：

  10.1002/adsc.202100929

文献信息

• I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea
  作者：Yan-Ping Zhu、Jing-Jing Yuan、Qin Zhao、Mi Lian、Qing-He Gao、Mei-Cai Liu、Yan Yang、An-Xin Wu

  DOI：10.1016/j.tet.2011.10.074

  日期：2012.1

  A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a–f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds

  开发了一种由易得的甲基酮/不饱和甲基酮和硫脲组成的简洁高效的一锅法，用于在I 2 / CuO介质下合成2-氨基噻唑。该方法可以高度立体选择性地获得4-乙烯基-2-氨基噻唑的电子异构体（5a–f）。所有这些目标分子均通过NMR，HRMS和IR光谱进行了表征。此外，通过X射线晶体学分析进一步确定目标化合物3c和5b。
• Formation of Unsymmetrical 1,4-Enediones via A Focusing Domino Strategy: Cross-Coupling of 1,3-Dicarbonyl Compounds and Methyl Ketones or Terminal Aryl Alkenes
  作者：Meng Gao、Yan Yang、Yan-Dong Wu、Cong Deng、Li-Ping Cao、Xiang-Gao Meng、An-Xin Wu

  DOI：10.1021/ol100473f

  日期：2010.4.16

  A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones

  通过聚焦多米诺骨牌战略已开发出一种由1,3-二羰基化合物和甲基酮或末端芳基烯烃高效合成不对称1,4-二烯键的方法。简单且容易获得的起始原料，温和的反应条件和非常简单的操作是反应的优势，可以直接合成各种不对称的1,4-二烯酮。
• Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation
  作者：Mark Kelada、John M D Walsh、Robert W Devine、Patrick McArdle、John C Stephens

  DOI：10.3762/bjoc.14.104

  日期：——

  A simple one-pot method for the microwave-assisted synthesis of substituted pyrazolo[1,5-a]pyrimidinones, a core scaffold in many bioactive and pharmaceutically relevant compounds, has been established. A variety of substituents was tolerated at the 2 and 5 positions, including functionalized aryls, heterocycles, and alkyl groups.

  建立了一种简单的一锅法，用于微波辅助合成取代的吡唑并[1,5-a]嘧啶酮（一种在许多生物活性和药学相关的化合物中的核心骨架）。在2和5位上可以耐受各种取代基，包括官能化的芳基，杂环和烷基。
• BETA-KETO-AMIDE DERIVATIVES USEFUL AS ION CHANNEL MODULATORS
  申请人：Nardi Antonio

  公开号：US20100137387A1

  公开（公告）日：2010-06-03

  This invention relates to novel β-keto-amide derivatives that are found to be potent modulators of ion channels, and in particular potassium channels and chloride channels, and, as such, are valuable candidates for the treatment of diseases or disorders as diverse as those which are responsive to the modulation of potassium channels.

  本发明涉及一种新型的β-酮酰胺衍生物，发现其是离子通道的有效调节剂，特别是钾通道和氯离子通道，并且因此是治疗各种响应于钾通道调节的疾病或疾病的有价值的候选药物。
• One pot direct synthesis of β-ketoesters via carbonylation of aryl halides using cobalt carbonyl
  作者：Poongavanam Baburajan、Kuppanagounder P. Elango

  DOI：10.1016/j.tetlet.2014.04.087

  日期：2014.6