• Bulletin of the Korean Chemical Society
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• 제10권2호
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• pp.151-154
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• 1989

4-Methoxy-4-methylcyclohexa-2,5-dienone 1 in aqueous sulfuric acid underwent the normal dienone-phenol rearrangement with methyl group migration. The fact that methyl is migrating group and methoxy is remaining group can be rationalized by the stabilization of positive charge at C-4 during the transition state. Methoxy methyl dienone 1 $((H_0)_{1/2} = - 4.6)$ is less basic than 4,4-dimethylcyclohexa-2,5-dienone whose half protonation acidity is reported as - 3.15 or - 3.66. This basicity difference comes from the unstabilization of the protonated methoxy methyl dienone 1 due to the electron withdrawing inductive effect of a methoxy group.

• Archives of Pharmacal Research
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• 제15권1호
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• pp.87-90
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• 1992

The syntheses of novel heterocyclic base modified pyrimidine nucleosides are described. 5, 6-dimethyl-4-hydroxy-3-methoxy-1-$(\beta$-D-ribofuranosyl)2(1H)-pyridinone 7 was synthesized by condensation of silylated 5, 6-dimethyl4-hydroxy-3-methoxy-2(1H)-pyridione 7 was synthesized by condensation of silylated 5, 6-dimethyl-4-hydroxy-3-methoxy-2(1H)-pyridinone with $\beta$-D-ribofuranose-1-acetate-2, 3, 5-tribenzoate in dichloroethane in the presence of Lewis acid followed by debenzoylation. The 2, 2'-anhydro-5, 6-dimethyl-2-hydroxy-3-methoxy-1-$\beta$-D-arabinofuranosyl-4-pyridinone 8 was obtained from the reaction of the free ribonucleoside 7 and diphenyl carbonate in DMF. None of these compounds showed any significant antiviral ad antitumor activities in vitro tests.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1994년도 춘계학술대회 and 제3회 신약개발 연구발표회
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• pp.218-218
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• 1994

화합물 9-methoxy-6-oxo-3,4,4a,5-tetrahydro-3-hydroxy-2,2-dimethyl-naphtho[1,2〕pyran(1)의 전구물질인 7-methoxy-4-oxo-2-prenyl-1-tetralol을 다음과 같은 방법으로 합성하였다. 7-Methoxy-$\alpha$-tetralone에 LDA를 처리한 후, prenyl bromide를 반응시켜 7-methoxy-2-prenyl-1-tetralone을 제조했다 (수율 66%). 7-Methyl-2-prenyl-1-tetralone을 L-seleclride로 환원하여 cis-2-prenyl-1-tetralol을98% 수율로 얻었다. cis-2-Prcnyl-1-tetralol을pyridine 존재하에서 acetic anhydride로서acetylation한 다음 PDC로 산화시켜 4-acetoxy-3-prenyl-1-tetralone을 합성하였다 (수율 45%). cis-4-Acetoxy-3-prenyl-1-tetralone을 가수분해하여 cir-7-methoxy-4-oxo-2-prenyl-1-tenalol을 합성하였다. 6,7-Dimethoxy-4-oxo-2-prenyl-1-letralol도 동일한 방법으로 합성하였다.

• 대한화학회지
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• 제39권8호
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• pp.657-665
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• 1995

여러가지 비대칭 벤질 에테르들과 벤질 알킬 에테르들을 $CH_3CO_2Et$-NaOCI수용액(6.6 mol eq.)의 2상 용매계에서 4-methoxy-2, 2, 6, 6,-tetramethylpiperidine-1-oxyl(0.03 mol eq., 4-methoxy-TEMPO)을 이용하여 산화시키면 벤조에이트로 산화가 일어난다. 4-methoxy-TEMPO는 2차 산화제인 NaOCI에 의하여 본반응의 산화제인 N-oxo-4-2, 2, 6, 6, -tetramethyl-piperidium 염(N-oxoammonium 염)으로 변환된다. N-oxoammonium 염은 에테르를 산화시키고 N-hydroxy-4-methoxy-2, 2, 6, 6,-tetramethylpiperidine(hydroxyamine)으로 환원된다. Hydroxy-amine은 NaOCI에 의하여 N-oxoammonium 염으로 순환 재생되므로 4-methoxy-TEMPO는 촉매량 사용하였다. 이 반응은 또한 조촉매인 KBr(0.03 mol eq.)가 필수적이고 반응 중 pH는 8.0 이하로 유지되어야 한다. 0 - 5$^{\circ}C$의 반응 온도로 2.5시간 반응시키면 대부분 벤조에이트로 산화 되었다. 벤질 알킬 에테르들의 선택성 산화는 수소의 산도와 알킬기의 입체효과에 영향을 받음이 고찰되었다.

• Bulletin of the Korean Chemical Society
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• 제33권6호
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• pp.2012-2016
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• 2012

A convenient synthetic route has been developed to synthesize 5-(4-((2-phenylthiazol-4-yl) methoxy)phenyl)-3-(4-sustituted phenyl)pyrazolines (5a-f) and 5-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-3-(4-substituted phenyl)isoxazolines (6a-f) starting from 2-phenyl-4-chloromethylthiazole (1). The chloromethylthiazole (1) was first condensed with 4-hydroxy benzaldehyde (2) for obtaining 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3). Claisen-Smidth condensation of 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3) and acetophenones has been carried in alkaline alcohol and obtained 3-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-1-(4-substituted phenyl)prop-2-en-1-ones (4a-f). The cyclocondensation of 2-propen-1-ones has been first time carried separately with hydrazine hydrate and hydroxylamine hydrochloride in aqueous micellar tetradecyltrimethylammonium bromide (TTAB) medium for getting the titled heterocycles with good to excellent yields.

• 약학회지
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• 제41권6호
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• pp.724-729
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• 1997

New 7-Halo-4-hydroxy-2-allyl-N-3-(4-methoxy-2-carboxylic acid pyrrolidinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide derivatives were synthesized through the condensation of 7-halo-4-hydroxy-2-allyl-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxide with 4-methoxy L-proline.

• 공업화학
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• 제9권3호
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• pp.413-418
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• 1998

Methoxy polyoxyethylene dodecanoate류($C_{11}H_{23}COO(CH_2CH_2O)_nCH_3$)는 고체촉매를 이용하여 지방산 메틸에스테르에 에틸렌옥사이드를 부가시켜 얻어지는 비이온성 계면활성제의 일종이다. 이들은 지방알코올을 이용한 비이온성 계면활성제 polyoxyethylene dodecyl ether류($C_{12}H_{25}O(CH_2CH_2O)nH$)보다 경제성이 높은 이점을 가지고 있다. 이 연구는 이들 두 종류의 비이온성 계면활성제에 대하여 비이온성 계면활성제/물/오일의 3성분계에서 일어나는 상거동에 관련된 오일의 가용화량과 phase inversion temperature(PIT)에서의 계면장력 및 세정성을 비교하여 methoxy polyoxyethylene dodecanoate의 세제용 비이온성 계면활성제로서의 적용 가능성을 확인하기 위해 수행하였다. Methoxy polyoxyethylene dodecanoate는 3성분계의 상거동에서 hexadecane에 대해 10~18%의 오일가용화량을 나타내므로서 polyoxyethylene dodecyl ether보다 약 6%의 높은 가용화력을 보여주었다. 또한, 각각의 PIT 조건에서 methoxy polyoxyethylene dodecanoate는 0.0124~0.0176 dyne/cm, polyoxyethylene dodecyl ether는 0.0130~0.0163 dyne/cm의 계면장력을 나타내었고 세정력에 있어서는 methoxy polyoxyethylene dodecanoate는 82.1~83.2%, 그리고 polyoxyethylene dodecyl ether는 78.5~80.4%로 methoxy polyoxyethylene dodecanoate가 polyoxyethylene dodecyl ether에 비해 높은 세정성을 나타내었다. methoxy polyoxyethylene dode-canoate의 우수한 세정 성능은 polyoxyethylene dodecyl ether에 비해 다소 높은 오일가용화력과 이에 관련된 PIT에서의 계면장력 저하효과에 기인된 것으로 판단된다.

• 대한화학회지
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• 제58권6호
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• pp.569-574
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• 2014

The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using $Pb(OAc)_4/HClO_4$ in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di-2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-${\alpha}$-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.

• Bulletin of the Korean Chemical Society
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• 제16권1호
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• pp.47-52
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• 1995

The mechanism of the photodecomposition of 2-methoxy-1,2-diphenyl diazoethane has been investigated in methanol and isoprene using time-resolved laser flash photolysis techniques. The reaction of triplet carbene which is generated from 2-methoxy-1,2-diphenyl diazoethane with methanol is believed to proceed via thermal excitation to the singlet state. The activation energy and enthalpy are consistent with a mechanism involving thermal equilibrium between the triplet and singlet state followed by the reaction of the singlet with methanol to give ether.

• Archives of Pharmacal Research
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• 제28권7호
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• pp.750-755
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• 2005

A series of 2-arylamino-5-hydroxy-naphthalene-1,4-diones, 3-arylamino-5-methoxy-naphthalene-1,4-diones, and 2-arylamino-3chloro-5-hydroxy-naphthalene-1,4-diones were synthesized and tested for in vitro antifungal activity against the species Candida and Aspergillus niger. Among those tested, 3-arylamino-5-methoxy-naphthalene-1,4-diones exhibited potent antifungal activity. In general, the 3-arylamino-5-methoxy-naphthalene-1,4-diones showed more potent antifungal activity than the 2-arylamino-5-hydroxy-naphthalene-1,4-diones and the 2-arylamino-3-chloro-5-hydroxy-naphthalene-1,4-diones.