3-环丙基-3-羰基-丙酸乙酯 | 24922-02-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-环丙基-3-羰基-丙酸乙酯
• 中文别名: 3-环丙基-3-氧代丙酸乙酯
• 英文名称: Ethyl 3-cyclopropyl-3-oxopropionate
• 英文别名: ethyl cyclopropanecarbonylacetate；ethyl 3-cyclopropyl-3-oxopropanoate
• CAS: 24922-02-9
• 化学式: C₈H₁₂O₃
• mdl: MFCD00184570
• 分子量: 156.181
• InChiKey: LFSVADABIDBSBV-UHFFFAOYSA-N

物化性质

• 沸点：
  73℃/1mm
• 密度：
  1.058 g/mL at 25 °C
• 闪点：
  >96℃
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2918300090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Ethyl 3-cyclopropyl-3-oxopropanoate
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ethyl 3-cyclopropyl-3-oxopropanoate
Ingredient name:
CAS number: 24922-02-9

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H12O3
Molecular weight: 156.2

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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.

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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

制备方法与用途

用途

3-环丙基-3-羰基-丙酸乙酯主要用作有机合成和医药化学中间体。它可用于药物分子、农药以及染料的合成。

制备

在0℃下，将吡啶（3毫升）、2,2-二甲基-1,3-二氧杂环己烷-4,6-二酮（15.3毫摩尔，1.00当量）和10毫升的二氯甲烷加入到100毫升圆底烧瓶中。得到的混合物搅拌5分钟后，在10分钟内将酰基氯（15.3毫摩尔，1.00当量）溶解在20毫升二氯甲烷中的溶液逐滴加至上述反应体系中。观察到该混合物变为橙色后，继续在0℃下搅拌反应30分钟，随后转移至室温并搅拌1小时。接着向混合物中加入30毫升的二氯甲烷，并用40毫升水洗涤四次。分离出有机层，使用MgSO4干燥后过滤，再将滤液中的溶剂旋干。然后将相应的二酮溶解于乙醇（40毫升）中，在回流下加热反应3小时并蒸发溶剂即可得到3-环丙基-3-羰基-丙酸乙酯。

反应信息

• 作为反应物：
  描述：

  3-环丙基-3-羰基-丙酸乙酯 在 氢氧化钾 、 碘苯二乙酸 、 碘 、 4-甲基苯磺酸吡啶 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 为溶剂， 生成 2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline
  参考文献：
  名称：

  A novel synthetic method of HMG-CoA reductase inhibitor NK-104 via a hydroboration-cross coupling sequence

  摘要：

  The regioselective hydroboration of ethyl (3R, 5S)-3,5-isopropylidenedioxy-6-heptynoate, followed by the cross-coupling reaction with an aryl halide, provides ethyl (3R, 5S, 6E)-7-aryl-3,5-isopropylidenedioxy-6-heptenoate, a precursor of a highly potent HMG-CoA reductase inhibitor NK-104.

  DOI：

  10.1016/s0040-4039(00)61407-7
• 作为产物：
  描述：

  5-(cyclopropylhydroxymethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 以 乙醇 为溶剂， 生成 3-环丙基-3-羰基-丙酸乙酯
  参考文献：
  名称：

  发现新型二氢咪唑并噻唑衍生物作为p53–MDM2蛋白-蛋白相互作用抑制剂：合成，生物学评估和结构-活性关系

  摘要：

  我们从Nutlins作为最初的线索开始，设计并生成了双环支架，旨在将顺式-双氯苯基部分置于与MDM2可能发生疏水相互作用的等效位置。结果，我们发现了具有二氢咪唑并噻唑支架的新型MDM2抑制剂。在分子模型的辅助下，对二氢咪唑并噻唑支架上侧链的进一步研究导致化合物显示出与Nutlin-3a几乎相同的体外效价。

  DOI：

  10.1016/j.bmcl.2012.08.086

文献信息

• Access to Polysubstituted (Furyl)methylthioethers via a Base-Promoted S-H Insertion Reaction of Conjugated Enynones
  作者：Wanqing Wu、Yang Chen、Meng Li、Weigao Hu、Xuemin Lin

  DOI：10.1021/acs.joc.9b02053

  日期：2019.11.15

  diverse functionalized (2-furyl)methylthioether derivatives via base-promoted S-H insertion of conjugated enynones with thiophenols or thiols has been developed. This reaction features readily available starting materials, high atom economy, broad substrate scope, and versatile operation. Moreover, the synthetic utility of this method has been demonstrated by the efficient synthesis of the CNKSPR1 inhibitor

  已经开发了一种方便和适用的方法，该方法通过将共轭烯酮与硫酚或硫醇进行碱促进的S​​H插入来构建多种官能化的（2-呋喃基）甲硫基醚衍生物。该反应具有容易获得的起始原料，高原子经济性，广泛的底物范围和多功能操作的特点。此外，该方法的合成效用已通过CNKSPR1抑制剂前体的有效合成和谷胱甘肽的后期官能化得到了证明。
• NITROGEN-CONTAINING HETEROCYCLIC COMPOUND OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20150322063A1

  公开（公告）日：2015-11-12

  A compound represented by Formula [1] (in the formula, Z 1 represents N, CH, or the like; X 1 represents NH or the like; R 1 represents a heteroaryl group or the like; each of R 2 , R 3 , and R 4 represents a hydrogen atom, a halogen atom, an alkoxy group, or the like; and R 5 represents a heteroaryl group or the like) or salt thereof.

  由式[1]表示的化合物（在该式中，Z表示N、CH或类似物；X表示NH或类似物；R表示杂环烷基或类似物；R2、R3和R4中的每一个表示氢原子、卤原子、烷氧基或类似物；R5表示杂环烷基或类似物）或其盐。
• [EN] cGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU CGAS
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017176812A1

  公开（公告）日：2017-10-12

  Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  揭示了一种新型化合物的化学式（I），这些化合物是cGAS拮抗剂，涉及到这些化合物的制备方法、包含这些化合物的药物组合物，以及它们在医学治疗中的应用。
• Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20140128372A1

  公开（公告）日：2014-05-08

  The present application relates to novel substituted imidazo[1,2-a]pyridine-3-carboxamides, to processes for their preparation, to their use alone or in combinations for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular disorders.

  本申请涉及新型取代咪唑[1,2-a]吡啶-3-羧酰胺，其制备方法，单独或组合使用以治疗和/或预防疾病，以及用于制备治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病。
• Pyridine anchors for HMG-CoA reductase inhibitors
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05506219A1

  公开（公告）日：1996-04-09

  Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesterolemic agents are provided which have a quinoline or a pyridine anchor attached by means of a linker to a binding domain sidechain, which compounds inhibit the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase.

  提供了一些有用的化合物，这些化合物可作为胆固醇生物合成抑制剂，因此可作为降胆固醇药物。这些化合物具有喹啉或吡啶锚点，通过连接剂连接到结合域侧链，这些化合物抑制酶3-羟基-3-甲基戊二酰辅酶A还原酶。