Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | 유충규 | - |
dc.contributor.author | 宋基春 | - |
dc.creator | 宋基春 | - |
dc.date.accessioned | 2016-08-26T10:08:22Z | - |
dc.date.available | 2016-08-26T10:08:22Z | - |
dc.date.issued | 1991 | - |
dc.identifier.other | OAK-000000017316 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/197290 | - |
dc.identifier.uri | http://dcollection.ewha.ac.kr/jsp/common/DcLoOrgPer.jsp?sItemId=000000017316 | - |
dc.description.abstract | (+)-Dihydrocarvone(p-mentha-8-ene-2-one)을 alkali 촉매하에서 formaldehyde로 hydroxymethylation하여, 1β-hydroxymethy1-p-mentha-8-ene-2-one(Ⅰ)과 lα-hydroxymethy1-p-mentha-8-ene-2-one(Ⅱ)을 합성하였다. 이 반응은 aldol condensation으로 ketone의 α-위치(C-1)에 regiospecific하게 진행하였다. Ⅰ과 Ⅱ를 LiAlH_(4)로 환원하여 1β-hydroxymethy1-p-mentha-8-ene-2β-ol(Ⅲ)과 1α -hydroxymethy1-p-mentha-8-ene-2β-ol(Ⅳ)을 얻었다. 그리고 Ⅰ과 Ⅱ를 CrO_(3)로 Corey oxdation법과 Jones oxidation법에 의해 각각 산화하여 1β-formy1-p-mentha-8-ene-2-one(Ⅴ), 1α-formy1-p-mentha-8-ene-2-one(Ⅵ), 1β-carboxy-p-mentha-8-ene-2-one(Ⅶ), 1α-carboxy-p-mentha-8-ene-2-one(Ⅷ)을 합성하였다. 또한 Ⅰ과 Ⅱ를 tosylester화 하여 LiALH_(4)로 환원하고, 다시 CrO_(3)로 산화하여 1-methy1-p-mentha-8-ene-2-one(Ⅸ)를 얻었다. 새로이 합성된 물질 Ⅰ-Ⅸ 중 Ⅶ,Ⅷ,Ⅸ 등은 carvone, camphor 계열의 항을 지닌다.;The synthetic product of l-hydroxymethyl-p-mentha-8-ene-2-one was afforded by the reaction of dihydrocarvone with formaldehyde, This reaction involves the aldol condensation. The preferential position of formaldehyde is methyl substituted α-carbon atom where the 1.2-enolate of p-mentha-8-ene-2-one is regiospecifically formed. The hydroxymethylation of dihydrocarvone also proved to occur regiospecifically in the position of α-methyl substituted ketone(C-1). When I-hydroxymethyl-p-mentha-8-ene-2-one reacted with LiAlH_(4). l-hydroxymethyl-p-mentha-8-ene-2β-o1 was obtained. l-Hydroxymethyl-p-mentha-8-ene-2-one also reacted with chromic acid to give 1-formyl-p-mentha-8-ene-2-one and l-carboxy-p-mentha-8-ene-2-one. When the hydroxymethyl group of l-hydroxymethyl-p-mentha-8-ene-2-one was reduced to methyl group, l-methyl-p-mentha-8-ene-2-one was obtained. Some of these new compounds have certain odor. | - |
dc.description.tableofcontents | 목차 = ⅲ 논문개요 = ⅴ Ⅰ. 서론 = 1 Ⅱ. 실험재료 및 방법 = 6 1. 시약 및 기기 = 6 2. 실험방법 = 8 1) Dihydrocarvone과 formaldehyde의 반응 (Ⅰ,Ⅱ) = 8 2) 1-Hydroxymethyl-p-mentha-8-ene-2-one의 환원 (Ⅲ,Ⅳ) = 9 3) 1-Formyl-p-mentha-8-ene-2-one의 합성 (Ⅴ,Ⅵ) = 10 4) 1-Carboxy-p-mentha-8-ene-2-one의 합성 (Ⅶ,Ⅷ) = 10 5) 1-Methyl-p-mentha-8-ene-2-one의 합성 (Ⅸ) = 12 Ⅲ. 결과 및 고찰 = 13 1. Dihydrocarvone과 Formaldehyde의 반응 = 13 1.1 Ⅰ과 Ⅱ의 spectral data의 해석 = 14 1.2 Ⅰ과 Ⅱ의 Configuration = 15 2. 1β-Hydroxymethyl-p-mentha-8-ene-2β-ol(Ⅲ)과 1α-Hydroxymethyl-p-mentha-8-ene-2β-ol(Ⅳ)의 합성 = 15 3. 1β-Formyl-p-mentha-8-ene-2-one(Ⅴ)와 1α-Formyl-p-mentha-8-ene-2-one(Ⅵ)의 합성 = 18 4. 1β-Carboxy-p-mentha-8-ene-2-one(Ⅶ)과 1α-Carboxy-p-mentha-8-ene-2-one(Ⅷ)의 합성 = 19 5. 1-Methyl-p-mentha-8-ene-2-one(Ⅸ)의 합성 = 21 6. Hydroxymethylation의 Regiospecificity의 고찰 = 21 Ⅳ. 결론 = 23 참고문헌 = 24 부록 = 27 Abstract = 38 | - |
dc.format | application/pdf | - |
dc.format.extent | 959253 bytes | - |
dc.language | kor | - |
dc.publisher | 이화여자대학교 대학원 | - |
dc.subject | Dihydrocarvone | - |
dc.subject | Formaldehyde | - |
dc.subject | 향료 | - |
dc.subject | 합성 | - |
dc.title | Dihydrocarvone과 Formaldehyde에 의한 향료 합성 | - |
dc.type | Master's Thesis | - |
dc.title.translated | Synthesis of odorants by the reaction of dihydrocarvone with formaldehyde | - |
dc.format.page | 45 p. | - |
dc.identifier.thesisdegree | Master | - |
dc.identifier.major | 대학원 약학과 | - |
dc.date.awarded | 1991. 2 | - |