2-(4-氟苯基)丙二酸二乙酯 | 2965-90-4

• 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: 2-(4-氟苯基)丙二酸二乙酯
• 英文名称: diethyl 2-(4-fluorophenyl)malonate
• 英文别名: 2-(4-fluorophenyl)malonic acid diethyl ester；diethyl (4-fluorophenyl)malonate；diethyl 2-(4-fluorophenyl)propanedioate
• CAS: 2965-90-4
• 化学式: C₁₃H₁₅FO₄
• 分子量: 254.258
• InChiKey: QHPZGTQIXUSMBA-UHFFFAOYSA-N

物化性质

• 沸点：
  161-162 °C(Press: 15 Torr)
• 密度：
  1.173±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2917399090
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Diethyl 2-(4-fluorophenyl)malonate
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: Diethyl 2-(4-fluorophenyl)malonate
CAS number: 2965-90-4

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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.

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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.

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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.

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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.
Store in closed vessels, refrigerated.
Storage:

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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.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H15FO4
Molecular weight: 254.3

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

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(4-氟苯基)丙二酸二乙酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 sodium hydroxide 、 锌 、 2-二环己基磷-2,4,6-三异丙基联苯 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 54.67h， 生成 3-(4-fluorophenyl)-6-(hydroxy(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methyl)-8-methylquinoline-2,4-dicarbonitrile
  参考文献：
  名称：

  HETEROARYL LINKED QUINOLINYL MODULATORS OF RORyt

  摘要：

  本发明涵盖了Formula I的化合物，其中：R1、R2、R3、R4、R5、R6、R7、R8和R9在规范中定义。该发明还涵盖了一种治疗或改善综合征、疾病或疾病的方法，其中所述综合征、疾病或疾病为类风湿性关节炎或银屑病。该发明还涵盖了通过给哺乳动物施用至少一种权利要求1中的化合物的治疗有效量来调节RORγt活性的方法。

  公开号：

  US20140107097A1
• 作为产物：
  描述：

  对氟苯乙酰氯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(4-氟苯基)丙二酸二乙酯
  参考文献：
  名称：

  羟烷基叠氮化物与酮的施密特反应中的异常束缚效应：阳离子-π 和伪轴苯基的空间稳定

  摘要：

  路易斯酸促进的手性 2-芳基-3-叠氮基-1-丙醇与 4-取代环己酮的反应生成亚胺醚并最终生成己内酰胺（在水解步骤之后）。在这项研究中，表明这些反应提供了可变比例的产物，这取决于苯基的电子性质。这些结果在决定产物的反应中间体中阳离子-π 稳定作用的背景下进行解释。值得注意的是，当使用含有季铵盐中心的叠氮基丙醇试剂时，选择性最佳；对照实验表明，在该结果中观察到的高选择性取决于提供主要产物的中间体中假轴芳基的自由旋转。

  DOI：

  10.1021/ja0382361

文献信息

• Air- and Light-Stable <i>S</i>-(Difluoromethyl)sulfonium Salts: <i>C</i>-Selective Electrophilic Difluoromethylation of β-Ketoesters and Malonates
  作者：Sheng-Le Lu、Xin Li、Wen-Bing Qin、Jian-Jian Liu、Yi-Yong Huang、Henry N. C. Wong、Guo-Kai Liu

  DOI：10.1021/acs.orglett.8b03067

  日期：2018.11.2

  Air- and light-stable electrophilic difluoromethylating reagents, S-(difluoromethyl)-S-phenyl-S-(2,4,6-trialkoxyphenyl) sulfonium salts were successfully developed, and the introduction of intramolecular hydrogen bonds plays a crucial role for the stabilities and reactivities of these reagents. C-selective difluoromethylation of a broad range of β-ketoesters and malonates proceeded smoothly under mild

  空气和光稳定的亲电子二氟甲基化试剂，S-（二氟甲基）-S-苯基-S-（2,4,6-三烷氧基苯基）salts盐已成功开发，并且分子内氢键的引入对于该化合物起着至关重要的作用。这些试剂的稳定性和反应性。在温和的反应条件下，各种β-酮酸酯和丙二酸酯的C选择性二氟甲基化反应平稳进行，从而以良好的C / O区域选择性提供了良好至优异的收率。
• Bench‐Stable <i>S</i> ‐(Monofluoromethyl)sulfonium Salts: Highly Efficient <i>C</i> ‐ and <i>O</i> ‐Regioselective Monofluoromethylation of 1,3‐Dicarbonyl Compounds
  作者：Wen‐Bing Qin、Jian‐Jian Liu、Zhongyan Huang、Xin Li、Wei Xiong、Jia‐Yi Chen、Guo‐Kai Liu

  DOI：10.1002/ejoc.202000998

  日期：2020.9.30

  Novel bench‐stable S‐(monofluoromethyl)‐S‐phenyl‐S‐(2,4,6‐trialkoxyphenyl)sulfonium salts were readily prepared for C‐ and O‐regioselective monofluoromethylation of 1,3‐dicarbonyl compounds in good to excellent yields under mild reaction conditions.

  新型稳定的S-（单氟甲基）-S-苯基-S-（2,4,6-三烷氧基苯基）ulf盐易于制备，可用于1,3-二羰基化合物的C和O区域选择性单氟甲基化在温和的反应条件下。
• OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS
  申请人：The Governors of the University of Alberta

  公开号：US20180186721A1

  公开（公告）日：2018-07-05

  Described herein are methods of oxidative coupling of aryl boron reagents with sp 3 -carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

  本文描述了一种利用氧化偶联芳基硼试剂与sp3-碳亲核试剂进行反应的方法，以及通过氧化催化实现马隆酸半酯的环境脱羧芳基化。
• Arylation of diethyl malonate and ethyl cyanoacetate catalyzed by palladium/di-tert-butylneopentylphosphine
  作者：Jeffrey G. Semmes、Stephanie L. Bevans、C. Haddon Mullins、Kevin H. Shaughnessy

  DOI：10.1016/j.tetlet.2015.01.072

  日期：2015.6

  α-Arylated carbonyl derivatives are important structural motifs in many natural products and pharmaceutically active compounds. Although arylation of simple monocarbonyl compounds is a well-established methodology, metal-catalyzed arylation of β-dicarbonyl derivatives is significantly more challenging. The ability of β-dicarbonyl anions to bind to palladium in a κ2-O,O mode, rather than the κ1-C-bound

  在许多天然产物和药物活性化合物中，α-芳基化羰基衍生物是重要的结构基序。尽管简单的单羰基化合物的芳基化是一种公认​​的方法，但金属催化的β-二羰基衍生物的芳基化更具挑战性。β二羰基的阴离子结合至钯在κ的能力2 - ø，ö模式，而不是κ 1 - c ^结合的模式键形成所需的，经常导致催化剂体系的失活。烯醇盐的C-结合形式可通过使用空间需求的配体来促进。在此，我们报告中指出，空间要求的二叔丁基丁基新戊基膦（DTBNpP）配体与Pd（dba）2结合为芳基溴化物和氯化物与丙二酸二乙酯的偶联提供了有效的催化剂。Pd / DTBNpP系统还催化芳基溴化物与氰基乙酸乙酯的偶联。
• First Desymmetrization of 1,3-Propanediamine Derivatives in Organic Solvent. Development of a New Route for the Preparation of Optically Active Amines
  作者：Eduardo Busto、Vicente Gotor-Fernández、Jose Montejo-Bernardo、Santiago García-Granda、Vicente Gotor

  DOI：10.1021/ol701720m

  日期：2007.10.1

  The chemical synthesis and enzymatic desymmetrization of a panel of prochiral diamines have been successfully described for the first time using lipases in organic solvents. A family of 2-aryl-1,3-propanediamines has been obtained with high enantiopurity and good yields in the PSL-catalyzed reaction using diallyl carbonate in 1,4-dioxane.

  首次在有机溶剂中使用脂肪酶成功地描述了一组前手性二胺的化学合成和酶促脱对称。使用碳酸二烯丙酯在1,4-二恶烷中的PSL催化反应中，获得了高对映体纯度和良好收率的2-芳基-1,3-丙二胺家族。