3-甲基-4-氧代-2-丁烯酸乙酯 | 41891-38-7

• 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-甲基-4-氧代-2-丁烯酸乙酯
• 英文名称: 3-formyl crotonic acid ethyl ester
• 英文别名: ethyl 3-methyl-4-oxocrotonate；ethyl formylcrotonate；3-formyl-2-butenoic acid ethyl ester；ethyl 4-oxo-3-methylcrotonate；Ethyl 3-methyl-4-oxobut-2-enoate
• CAS: 41891-38-7
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: YLFXEUMFBVGYEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

SDS

Name:	Ethyl 3-formylcrotonate Material Safety Data Sheet
Synonym:
CAS:	41891-38-7

Section 1 - Chemical Product MSDS Name:Ethyl 3-formylcrotonate Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
41891-38-7	Ethyl 3-formylcrotonate		255-575-2

Hazard Symbols: F C
Risk Phrases: 11 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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. Will burn if involved in a fire. Flammable liquid and vapor.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Remove all sources of ignition.
Use a spark-proof tool.

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Section 7 - HANDLING and STORAGE
Handling:
Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Keep away from sources of ignition. Store in a cool, dry place.
Store in a tightly closed container. Flammables-area. Corrosives area.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 41891-38-7: 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: Clear liquid
Color: yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 188 - 190 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 2 deg C (> 35.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.045
Molecular Formula: C7H10O3
Molecular Weight: 142.15

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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, strong reducing agents, bases, acids.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 41891-38-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 3-formylcrotonate - 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
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.*
Hazard Class: 3 (8)
UN Number: 2924
Packing Group: II
IMO
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.
Hazard Class: 3 (8)
UN Number: 2924
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.
Hazard Class: 3 (8)
UN Number: 2924
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F C
Risk Phrases:
R 11 Highly flammable.
R 34 Causes burns.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 41891-38-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 41891-38-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 41891-38-7 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：

  3-甲基-4-氧代-2-丁烯酸乙酯 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 3-甲基-4-氧代丁酸乙酯
  参考文献：
  名称：

  All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use

  摘要：

  提供了全反式视黄醇的组合物：全反式-13,14-二氢视黄醛饱和酶及其使用方法。

  公开号：

  US20080249042A1
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 1,1-二甲氧基丙酮 在 potassium carbonate 、 盐酸 作用下， 以 水 、 二氯甲烷 为溶剂， 生成 3-甲基-4-氧代-2-丁烯酸乙酯
  参考文献：
  名称：

  多取代的无环二烯与Enals几何异构体的分子间Diels-Alder反应中的反常反应性和选择性

  摘要：

  研究了路易斯酸催化的多取代无环二烯与α，β-烯醛的E和Z异构体之间的分子间Diels-Alder反应。发现二烯与α，β-烯醛的Z-异构体选择性地反应。

  DOI：

  10.1021/acs.orglett.6b00783

文献信息

• Development of Non-<i>C</i>2-symmetric ProPhenol Ligands. The Asymmetric Vinylation of <i>N</i>-Boc Imines
  作者：Barry M. Trost、Chao-I (Joey) Hung、Dennis C. Koester、Yan Miller

  DOI：10.1021/acs.orglett.5b01755

  日期：2015.8.7

  The development and application of a new generation of non-C2-symmetric ProPhenol ligands is reported herein. Rational design of the ProPhenol ligand paved the way to the first catalytic and asymmetric vinylation of N-Boc imines via hydrozirconation giving rise to valuable allylic amines in excellent yields and enantioselectivities. The utility of this method was demonstrated by developing the shortest

  本文报道了新一代的非C 2-对称的ProPhenol配体的开发和应用。ProPhenol配体的合理设计为N- Boc亚胺通过氢化锆的首次催化和不对称乙烯基化铺平了道路，从而以极高的收率和对映选择性产生了有价值的烯丙基胺。通过开发最短的报道的选择性5-羟色胺再摄取抑制剂（SSRI）（-）-多巴西汀的不对称合成证明了该方法的实用性。
• Synthesis of the C(18)−C(34) Fragment of Amphidinolide C and the C(18)−C(29) Fragment of Amphidinolide F
  作者：Sudeshna Roy、Christopher D. Spilling

  DOI：10.1021/ol102345v

  日期：2010.11.19

  A convergent synthesis of the C(18)−C(34) fragment of amphidinolide C and the C(18)−C(29) fragment of amphidinolide F is reported. The approach involves the synthesis of the common intermediate tetrahydrofuranyl-β-ketophosphonate via cross metathesis, Pd(0)-catalyzed cyclization, and hydroboration−oxidation. The β-ketophosphonate was coupled to three side chain aldehydes using a Horner−Wadsworth−Emmons

  报道了amphidinolide C的C(18)-C(34)片段和amphidinolide F的C(18)-C(29)片段的收敛合成。该方法涉及通过交叉复分解、Pd(0)-催化环化和硼氢化-氧化合成常见的中间体四氢呋喃基-β-酮膦酸酯。使用 Horner-Wadsworth-Emmons (HWE) 烯化反应将 β-酮膦酸酯偶联到三个侧链醛上，得到二烯酮，然后用l- selectride还原得到双环内酯 C 和 F 的片段。
• Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions
  作者：Xingxing Wu、Bin Liu、Yuexia Zhang、Martin Jeret、Honglin Wang、Pengcheng Zheng、Song Yang、Bao-An Song、Yonggui Robin Chi

  DOI：10.1002/anie.201606571

  日期：2016.9.26

  enantioselective β‐carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N‐heterocyclic‐carbene‐bound α,β‐unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic

  公开了对映体的对映体选择性β-碳胺化反应。来自具有适当电子性质的受保护肼的氮原子很容易表现出亲核试剂的作用。将氮亲核试剂加到催化生成的N-杂环-卡宾键合的α，β-不饱和酰基偶氮中间体上，可不对称地构建新的碳-氮键。从我们的催化反应的吡唑烷酮产品是生物活性分子共同支架，并且可以容易地转化为诸如β有用的化合物3 -氨基-酸衍生物。
• Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
  作者：Franz-Lucas Haut、Christoph Habiger、Klaus Speck、Klaus Wurst、Peter Mayer、Johannes Nepomuk Korber、Thomas Müller、Thomas Magauer

  DOI：10.1021/jacs.9b07729

  日期：2019.8.28

  Here we present a comprehensive study on the [3+2]-cycloaddition of thiocarbonyl ylides with a wide variety of alkenes and alkynes. The obtained dihydro- and tetrahydrothiophenes products serve as exceptionally versatile intermediates providing access to thiophenes, dienes, dendralenes, and vic-quarternary carbon centers. The use of high-pressure conditions enables thermally unstable, sterically encumbered

  在这里，我们对硫代羰基叶立德与各种烯烃和炔烃的[3+2]-环加成进行了全面的研究。所获得的二氢和四氢噻吩产品作为用途极其广泛的中间体，提供了获得噻吩、二烯、树枝烯和八元碳中心的途径。高压条件的使用使得热不稳定、空间阻碍或中等反应性的底物能够在温和条件下进行环加成，从而将产率提高高达 58%。此外，我们还通过药物 NGB 4420 和替尼拉平的正式合成展示了其实用性。
• Modular Approaches to Lankacidin Antibiotics
  作者：Lingchao Cai、Yanmin Yao、Seul Ki Yeon、Ian B. Seiple

  DOI：10.1021/jacs.0c06648

  日期：2020.9.2

  Lankacidins are a class of polyketide natural products isolated from Streptomyces spp. that show promising antimicrobial activity. Owing to their complex molecular architectures and chemical instability, structural assignment and derivatization of lankacidins is challenging. Herein we describe three fully synthetic approaches to lankacidins that enable access to new structural variability within the

  兰卡西丁是从链霉菌属中分离出来的一类聚酮化合物天然产物。显示出有希望的抗菌活性。由于其复杂的分子结构和化学不稳定性，lankacidins 的结构分配和衍生化具有挑战性。在此，我们描述了三种完全合成的 lankacidins 方法，这些方法能够获得该类中新的结构变异性。我们使用这些路线系统地生成环状和非环状 lankacidins 的立体化学衍生物。此外，我们获得了在 C4 位带有甲基的新系列 lankacidin，这是一种旨在提高化学稳定性的修饰。在这项工作的过程中，我们发现 lankacidin 类的两种天然产物的报告结构是不正确的，我们确定了 2 的正确结构，18-seco-lankacidinol B 和iso-lankacidinol。我们还评估了几种 iso- 和 seco-lankacidin 抑制细菌生长和体外翻译的能力。这项工作有助于深入了解此类抗生素的丰富化学复杂性，并为进一步结构衍生化提供了途径。