• 제목/요약/키워드: Aldol condensation

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산, 염기 이원기능 금속-유기 구조체 촉매를 이용한 알돌 축합반응 (Aldol Condensation over Acid-Base Bifunctional Metal-Organic Framework Catalysts)

  • 정영민
    • 청정기술
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    • 제20권2호
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    • pp.116-122
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    • 2014
  • 수열합성 또는 후처리 방법을 통해 산 또는 염기능을 나타내는 다양한 종류의 이원기능 금속-유기 구조체 물질을 제조하여 대표적인 방향제 원료 중 하나인 자스민알데하이드(jasminaldehyde)를 합성하기 위한 벤즈알데하이드(benzaldehyde, $C_6H_5CHO$)와 헵탄알(heptanal, $C_6H_{13}CHO$)의 알돌 축합반응의 촉매로 활용하였다. 실험 결과, 산 또는 염기점 모두에서 축합반응이 진행되었으며, 촉매 성능은 기능기의 도입 여부 및 종류와 금속-유기 구조체의 물리적인 특성에 크게 의존하였다. Jasminaldehyde 선택도는 황산 기능기를 도입한 경우에는 금속-유기 골격체의 종류에 상관없이 감소하였으나, 아민 기능기를 도입한 경우에는 금속-유기 골격체의 종류에 따라 상반된 경향을 나타내었다. 평가한 촉매 중 MIL-101의 촉매 성능이 가장 우수하였는데, 이러한 결과는 MIL-101이 알돌 축합반응의 촉매로 작용하기에 충분한 산량과 적당한 산세기를 가지고 있으며, 세공 크기가 넓어 크기가 큰 생성물의 물질이동 측면에서 유리하기 때문인 것으로 판단된다.

Stereoselective Crossed-Aldol Condensation of Hetarylmethyl Ketones with Aromatic Aldehydes in Water : Synthesis of (2E)-3-Aryl-1-hetarylprop-2-en-1-ones

  • Basaif, Salem A.;Sobahi, Tatiq R.;Khalil, Ali Kh.;Hassan, Mohamed A.
    • Bulletin of the Korean Chemical Society
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    • 제26권11호
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    • pp.1677-1681
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    • 2005
  • Aldol condensation of 2-acetylthiophene, 2-acetylpyrrole and 2-acetylpyridine with different aromatic aldehydes were carried out in water in heterogeneous phases in the presence of cetyltrimethylammonium bromide as cationic surfactant at room temperature. All the reactions occur in a short time with excellent yields of steroselective hetarylpropanones in water as environmental friendly solvent.

Studies on Triterpenoid Corticomimetics (IV) - E-Ring Opening of Pomolic Acid by Retrograde Aldol Condensation

  • Han, Yong-Nam;Han, Byung-Hoon;Park, Eun-Tae;Kim, Tae-Hee
    • Archives of Pharmacal Research
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    • 제8권4호
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    • pp.221-227
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    • 1985
  • Acetyl-11-ketopomolic acid methyl ester (VI), mp 276-$278^{\circ}$ was synthesized from pomolic acid (III). The mild alkaline treatment of VI induced the opening of ring E on carbone skeleton to yield VII, and then VII was deacetylated to give VIII, mp 82-$84^{\circ}$ Compound VIII was established as 11, 19-diketo-18, 19-secoursolic acid methylester. The E-ring opening was believed to be due to regrograde aidol condensation.

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First Total Synthesis of Prorepensin with a Bis-Geranylated Chalcone

  • Jung, Eun-Mi;Lee, Yong-Rok
    • Bulletin of the Korean Chemical Society
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    • 제30권11호
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    • pp.2563-2566
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    • 2009
  • The first total synthesis of naturally occurring prorepensin with a bis-geranylated chalcone has been achieved by a convergent sequence. The key strategy involved in the synthesis of prorepensin was chalcone formation by aldol condensation of the corresponding geranylated acetophenone with geranylated benzaldehyde.

Synthesis and NMR Studies of (E)-1-Aryl-3-(2-pyrrolyl)-2-propenones and (E)-3-Aryl-1-(2-pyrrolyl)-2-propenones

  • Han Lee, In-Sook;Jeoung, Eun Ji;Lee, Chang Kiu
    • Bulletin of the Korean Chemical Society
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    • 제34권3호
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    • pp.936-942
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    • 2013
  • Series of (E)-1-aryl-3-(2-pyrrolyl)-2-propenones, that were aldol condensation products between pyrrole-2-carbaldehyde and m- and p-substituted acetophenones, were prepared and their $^1H$ and $^{13}C$ NMR spectra were examined to obtain the information on the conformation of the enone system. Similar studies were carried out with (E)-3-aryl-1-(2-pyrrolyl)-2-propenones that were prepared from 2-acetylpyrrole and m- and p-substituted benzaldehydes. The substituent chemical shifts were studied by applying the Hammett relationship.

p-Mentha-8-ene-2-one계 향료합성 (Synthesis of Odorants p-Mentha-8-ene-2-one Derivatives by the Reaction of Dihydrocarvone with Formaldehyde)

  • 유충규;송기춘
    • 약학회지
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    • 제35권4호
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    • pp.335-340
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    • 1991
  • The synthetic product of 1-hydroxymethyl-p-mentha-8-ene-2-one was afforded by the reaction between dihydrocarvone and formaldehyde. This reaction involves the aldol condensation. The preferential position of formaldehyde is methyl substituted .alpha.-carbon atom where these enols are regiospecifically formed. The hydroxymethylation of dihydrocarvone was also proved to happen regiospecifically in the position of .alpha.-methyl substituted ketone. When 1-hydroxymethyl-p-mentha-8-ene-2-one reacted with LiAIH$_{4}$, 1-hydroxymethyl-p-mentha-8-ene-2$\beta$-ol obtained. 1-Hydroxymethyl-p-mentha-8-ene-2-one reacted with PDC and chromic acid to give 1-formyl-p-mentha-8-ene-2-one and 1-carboxy-p-mentha-8-ene-2-one. When the hydroxymethyl group of 1-hydroxymethyl-p-menta-8-ene-2-one was reducted to methyl group, 1-methyl-p-menta-8-ene-2-one was obtained. Some of these new compound have certain odor. I, II have woody aroma and IV, V have camphory odors. IX has flowery minty odor.

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마이크로 반응기를 적용한 알돌 축합반응 생성물 제조연구 (A study of aldol condensation reaction product using a microreactor)

  • 김영준;이상서;손성광;송광호;최재훈
    • 한국정밀공학회:학술대회논문집
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    • 한국정밀공학회 2006년도 춘계학술대회 논문집
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    • pp.543-544
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    • 2006
  • 3-methyl-2-cyclopentenone is a valuable reaction intermediate for various high value added products. 3-methyl-2-cyclopentenone is not only expensive but also difficult to produce. 3-methyl-2-cyclopentenone can be synthesized by base catalyzed intermolecular aldol condensation. In this work, we studied a simple and practical method for synthesizing 3-methyl-2-cyclopentenone. Experimental results showed the advantages of the continuous flow process using a microreactor with kenic mixers for the synthesis of 3-methyl-2-cyclopentenone.

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