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Sunscreen and Knoevenagel condensation_Ethyl trans-4-methoxycinnamate

"Sunscreen and Knoevenagel condensation_Ethyl trans-4-methoxycinnamate"에 대한 내용입니다.
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최초등록일 2024.08.22 최종저작일 2024.05
유기화학실험 유기화학 실험레포트 화학과
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Sunscreen and Knoevenagel condensation_Ethyl trans-4-methoxycinnamate
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    • 🔬 유기화학 실험의 상세한 실험 절차와 메커니즘 설명
    • 🧪 Sunscreen 합성 과정의 전문적이고 체계적인 접근 방법 제공
    • 📊 NMR, UV 분광법 등 다양한 분석 기법의 실제 적용 사례 소개
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    "Sunscreen and Knoevenagel condensation_Ethyl trans-4-methoxycinnamate"에 대한 내용입니다.

    목차

    1. Title
    2. Purpose
    3. Theory
    4. Chemical and Apparatus
    5. Procedure
    6. 실험 시 주의해야 할 사항
    7. Data& Result
    8. Discussion
    9. Conclusion
    10. Reference

    본문내용

    1. Title: Sunscreen and Knoevenagel condensation: Ethyl trans-4-methoxycinnamat

    2. Purpose: 화장품의 차광제로 쓰이는 쓰이는 ethyl trans-4-methoxycinnamate를 합성한다.
    1) To synthesize a stereoisomer of 4-methoxycinnamic acid (3-(4-methoxyphenyl)-2-propenoic acid) via a Verley-Doebner reaction.
    2) To characterize the reaction product by 1H NMR, IR and UV spectroscopy.
    3) To deduce whether the product is the cis or trans stereoisomer.
    4) To synthesize and characterize a sunscreen analog, ethyl trans-4-methoxycinnamate ((E)-ethyl 3-(4-methoxyphenyl)-2-propenate) by an esterification reaction.
    5) To learn about the “cesium effect” in organic synthesis.
    To appreciate the relationship between the structure of UV light absorbers and their physical properties.

    3. Theory
    i. Knoevenagel condensation
    유기 화학에서 Knoevenagel condensation은 1890년대 Emil knoevenagel에 의해서 설명된 aldol reaction의 변형 형태로, 활성화된 수소 화합물이 carbonyl compound에 Nucleophilic addition되는 메커니즘을 거친다.

    참고자료

    · Fulmer, G. R., Miller, A. J., Sherden, N. H., Gottlieb, H. E., Nudelman, A., Stoltz, B. M., ... & Goldberg,
    · K. I. (2010). NMR chemical shifts of trace impurities: common laboratory solvents, organics, and
    · gases in deuterated solvents relevant to the organometallic chemist. Organometallics, 29(9), 2176- 2179.
    · Koen van Beurden, Steffijn de Koning, Dennis Molendijk & Jack van Schijndel (2020) The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds, Green Chemistry Letters and Reviews, 13:4, 349-364, DOI: 10.1080/17518253.2020.1851398
    · L.G wade, organic chemistry 8th ed, 자유아카데미, 2015, pp641-647

  • AI와 토픽 톺아보기

    • 1. Knoevenagel condensation
      The Knoevenagel condensation is an important organic reaction that involves the condensation of an active hydrogen compound, such as a malonic ester or a malononitrile, with an aldehyde or ketone in the presence of a base catalyst. This reaction is widely used in the synthesis of various heterocyclic compounds, α,β-unsaturated carbonyl compounds, and other important organic molecules. The mechanism of the Knoevenagel condensation involves the initial formation of an enolate intermediate, which then reacts with the carbonyl compound to form the desired product. The reaction is typically carried out under mild conditions and can be used to synthesize a wide range of compounds with diverse functional groups. Overall, the Knoevenagel condensation is a versatile and powerful tool in organic synthesis, and its applications continue to be explored in various fields of chemistry.
    • 2. Verley-Doebner reaction
      The Verley-Doebner reaction is a useful organic transformation that involves the condensation of an aldehyde with a malonic acid derivative, such as diethyl malonate or malononitrile, in the presence of a base catalyst. This reaction is particularly useful for the synthesis of α,β-unsaturated carbonyl compounds, which are important building blocks in organic synthesis. The mechanism of the Verley-Doebner reaction is similar to the Knoevenagel condensation, with the initial formation of an enolate intermediate that then reacts with the aldehyde. However, the Verley-Doebner reaction typically requires more forcing conditions, such as higher temperatures and longer reaction times, compared to the Knoevenagel condensation. Despite these challenges, the Verley-Doebner reaction remains a valuable tool in the synthetic chemist's toolbox, and its applications continue to be explored in various areas of organic chemistry.
    • 3. Cesium effect
      The Cesium effect, also known as the Cesium anomaly, is a phenomenon observed in organic chemistry where the presence of cesium cations (Cs+) can significantly enhance the reactivity and selectivity of certain organic reactions. This effect is particularly pronounced in reactions involving carbanions, such as alkylations, acylations, and condensations. The Cesium effect is believed to be due to the unique properties of the cesium cation, which has a large ionic radius and low electronegativity, leading to a high degree of polarization and increased ionic character in the resulting cesium-containing intermediates. This, in turn, can stabilize the carbanion intermediates and facilitate the desired reaction pathway. The Cesium effect has been exploited in various organic transformations, including the Reformatsky reaction, the Grignard reaction, and the Knoevenagel condensation, among others. Understanding and harnessing the Cesium effect can be a valuable tool in the synthetic chemist's arsenal, allowing for the development of more efficient and selective organic reactions.
    • 4. Ethyl trans-4-methoxycinnamate 합성
      Ethyl trans-4-methoxycinnamate is an important organic compound that has various applications, particularly in the cosmetics and personal care industries. The synthesis of this compound typically involves a Knoevenagel condensation reaction between 4-methoxybenzaldehyde and ethyl cyanoacetate, followed by a decarboxylation step to yield the desired trans-4-methoxycinnamate product. The Knoevenagel condensation step is crucial, as it allows for the introduction of the α,β-unsaturated carbonyl moiety, which is responsible for the UV-absorbing properties of the compound. The decarboxylation step then removes the ethyl ester group, leaving the trans-4-methoxycinnamate as the final product. The synthesis of this compound requires careful control of reaction conditions, such as temperature, solvent, and catalyst, to ensure high yields and selectivity. The purification of the final product may also involve techniques like recrystallization or column chromatography. Overall, the synthesis of ethyl trans-4-methoxycinnamate is an important process in the production of UV-absorbing compounds for use in sunscreens and other cosmetic applications.
    • 5. Sunscreen
      Sunscreens are an essential personal care product that play a crucial role in protecting the skin from the harmful effects of ultraviolet (UV) radiation. The active ingredients in sunscreens can be broadly classified into two categories: organic (chemical) filters and inorganic (physical) filters. Organic filters, such as ethyl trans-4-methoxycinnamate, work by absorbing UV radiation and converting it into heat energy, which is then dissipated. Inorganic filters, such as titanium dioxide and zinc oxide, work by reflecting and scattering the UV radiation away from the skin. The effectiveness of a sunscreen is measured by its sun protection factor (SPF), which indicates the degree of protection it provides against UVB radiation. In addition to SPF, sunscreens should also provide protection against UVA radiation, which can cause long-term skin damage and premature aging. Proper application and reapplication of sunscreen, along with other sun-safe behaviors, are crucial for maintaining skin health and reducing the risk of skin cancer and other UV-related skin conditions. As research continues to advance in the field of sunscreen technology, the development of more effective and cosmetically elegant sunscreen formulations will be an important area of focus.
    • 6. UV spectroscopy
      UV spectroscopy is a powerful analytical technique that is widely used in various fields of chemistry, including organic, inorganic, and biochemistry. This technique relies on the absorption of ultraviolet (UV) or visible light by molecules, which can provide valuable information about the structure and properties of the analyzed compounds. In organic chemistry, UV spectroscopy is particularly useful for the identification and characterization of conjugated systems, such as aromatic compounds and α,β-unsaturated carbonyl compounds. The absorption spectra of these compounds can provide insights into their electronic structure, the nature of their chromophores, and the extent of conjugation. Additionally, UV spectroscopy can be used to quantify the concentration of specific compounds in a sample, making it a valuable tool for analytical and preparative applications. The development of more advanced UV spectroscopic techniques, such as UV-Vis-NIR and two-dimensional UV spectroscopy, has further expanded the capabilities of this analytical method, allowing for the study of more complex molecular systems and the investigation of dynamic processes. Overall, UV spectroscopy remains an indispensable tool in the arsenal of modern analytical chemistry, with a wide range of applications in both research and industrial settings.
    • 7. NMR spectroscopy of stereoisomers
      Nuclear Magnetic Resonance (NMR) spectroscopy is a powerful analytical technique that is widely used in organic chemistry for the structural elucidation and characterization of organic compounds, including stereoisomers. The ability of NMR spectroscopy to distinguish between different stereoisomers, such as cis/trans or E/Z isomers, is particularly valuable in organic synthesis and natural product research. By analyzing the chemical shifts, coupling patterns, and other NMR parameters of the signals corresponding to the various protons and carbon atoms in a molecule, organic chemists can gain insights into the spatial arrangement of the atoms and the overall stereochemistry of the compound. This information is crucial for understanding the reactivity, stability, and biological properties of organic molecules, especially in the context of drug discovery and development. Furthermore, the advancement of NMR techniques, such as 2D NMR experiments (e.g., COSY, HSQC, HMBC), has significantly enhanced the ability to elucidate the stereochemistry of complex organic molecules, even in the presence of multiple stereogenic centers. As the field of organic chemistry continues to evolve, the role of NMR spectroscopy in the characterization and understanding of stereoisomeric compounds will remain essential for the advancement of both fundamental research and practical applications.

  • 자료후기

      Ai 리뷰
      제시된 실험 절차와 분석 결과를 통해 Verley-Doebner 반응과 Sn2 알킬화 반응을 이용해 sunscreen 물질을 성공적으로 합성하였으며, NMR과 UV 분광분석을 통해 생성물의 구조와 광학적 특성을 확인하였다.

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