• Bulletin of the Korean Chemical Society
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• 제8권3호
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• pp.211-214
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• 1987

Asymmetric reduction of a series of aliphatic ketones and representative other classes of ketones with potassium 9-O-isopinocampheyloxy-9-boratabicyclo[3.3.1]non ane (K 9-O-Ipc-9-BBNH) was studied. All the ketones examined were reduced smoothly to the corresponding alcohols in THF at -$78^{\circ}C$. Thus, the reduction of 2-butanone, 3-methyl-2-butanone, 3,3-dimethyl-2-butanone, 2-octanone, and 4-phenyl-2-butanone provides 51% ee, 61% ee, 44% ee, 35% ee, and 33% ee of optical inductions, respectively. The reduction of other classes of ketones gave 52% ee for 2,2-dimethylcyclopentanone, 47% ee for acetophenone, 23% ee for 3-acetylpyridine, 50% ee for methyl benzoylformate, 4.8% ee for 2-chloroacetophenone, 30% ee for trans-4-phenyl-3-butene-2-one, and 2% ee for 4-phenyl-3-butyn-2-one. Thus, the reagent was found to be most useful in the asymmetric reduction of acyclic and cyclic aliphatic series of ketones.

• Bulletin of the Korean Chemical Society
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• 제8권4호
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• pp.257-260
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• 1987

The asymmetric reduction of representative prochiral ${\alpha},{\beta}$-acetylenic ketones with a new chiral borohydride reducing agent, potassium 9-0-(1,2: 5,6-Di-O-isopropylidene-${\alpha}$ -D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane, 1, in THF at $-78^{\circ}C$ was studied. Structurally different acetylenic ketones such as internal ${\alpha},{\beta}$-acetylenic ketones $RC {\equiv} CCOCH_3$ and terminal ${\alpha},{\beta}$-acetylenic ketones $HC {\equiv} CCOR$ were chosen. Thus, the reduction of internal ${\alpha},{\beta}$-acetylenic ketones yields the corresponding propargyl alcohols, such as 67% ee for 3-hexyn-2-one, 75% ee for 5-methyl-3-hexyn-2-one, 86% ee for 5,5-dimethyl-3-hexyn-2-one, 74% ee for 3-nonyn-2-one and 61% ee for 4-phenyl-3-butyn-2-one. Terminal ${\alpha},{\beta}$-acetylenic ketones, such as 3-butyn-2-one, 1-pentyn-3-one, 4-methyl-1-pentyn-3-one and 1-octyn-3-one, are reduced to the corresponding alcohols with 59% ee, 17% ee, 44% ee and 12% ee of optical induction respectively. With one exception (4-methyl-1-pentyn-3-one), all propargyl alcohols obtained are enriched in R-enantiomers.

• 대한화학회지
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• 제52권4호
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• pp.369-379
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• 2008

• 대한화학회지
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• 제40권6호
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• pp.415-419
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• 1996

수소결합, 유전효과 그리고 입체효과는 케톤의 카르보닐 신축진동을 결정하는 요인이 된다. 케톤의 카르보닐 신축진동은 다양한 용매에서 케톤의 농도변화에 영향을 받는다. 비극성용매에서 카르보닐 신축진동은 케톤의 부피%가 증가함에 따라 낮은 파수로 이동하고 극성용매에서는 높은 파수로 이동한다. 용매 아세토니트릴에서 카르보닐 신축진동은 dimethyl ketone을 제외하고 케톤의 부피%가 증가함에 따라 높은 파수로 이동한다. 용매의 극성이 증가할수록 카르보닐 신축진동은 낮은 파수로 이동하고 혼합용매 $CHCI_3CCI_4$에서 부피%가 증가할수록 낮은 파수로 이동한다.

• Applied Biological Chemistry
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• 제31권3호
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• pp.292-297
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• 1988

토마토 과실의 향기성분을 생체흡착법, 파쇄흡착법 및 연속 수증기증류법으로 추출하고 GC와 GC-MS에 의해 동정하였다. 생체흡착법으로 추출한 향기성분은 80여 종 이상이 분리되었고 그 중 alcohols 10종, aldehydes 6종, ester 3종, ketones 4종, phenol 1종, acid 1종으로 총 25종을 동정하였다. 파쇄흡착법으로 추출한 향기성분은 100여종 이상이 분리되었고 그중 alcohols 12종, aldehydes 6종, Ketones 5종, esters 5종, phenols 2종, hydrocarbon 1종, acid 1종으로 총 32종이 동정되었다. 연속수증기증류법으로는 향기성분 300여종 이상을 분리하였고 그 중 alcohols 19종, ester 9종, hydrocarbons 13종, aldehydes 8종, Ketones 9종, phenols 2종, lactones 2종, furans 2종, acid 1종, oters 2종으로 총 67종이 동정되었다. 연속수증기 증류법에 의해 동정한 성분 중 아직까지 MS에 의해 동정되지 않은 성분들은 hydrocarbons 11종, aldehydes, Ketones 및 other 각각 2종, alcohol, ester, lacton 및 furfural 각각 1종으로 총 21종이었다.

• Archives of Pharmacal Research
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• 제18권5호
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• pp.369-370
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• 1995

• Bulletin of the Korean Chemical Society
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• 제23권7호
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• pp.937-938
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• 2002

• 대한화학회지
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• 제51권2호
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• pp.115-124
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• 2007

α, β-불포화 케톤 유도체를 실리카-황산 촉매 하에서 비용매 교차 알돌 응축 반응법을 이용하여 합성하였다. 합성 수율은 90% 이상이었으며, 사용된 촉매는 회수 가능하였다. 합성돤 화합물들의 물리화학적인 특성은 IR, NMR, Mass 등의 분광학적 분석 방법을 이용하여 결정하였다. 케톤 생성물에 미치는 치환기 효과는 측정된 분광 데이터와 Hammet 치환기 상수간의 상관관계로 표현되는 다중 상관계수 방정식에 의하여 잘 설명될 수 있었다.

• Bulletin of the Korean Chemical Society
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• 제3권3호
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• pp.119-122
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• 1982

Rigid ${\alpha}$-oximino ketones containing two functional groups such as 2-oximino-1-acenaphthenone and 2-oximino-1-indanone were synthesized and the simultaneous reduction of the two functional groups of ${\alpha}$-oximino ketones by $LiAlH_4$ gave the corresponding amino alcohols, 2-amino-1-acenaphthenol and 2-amino-1-indanol. The yields of the reduction products of the ${\alpha}$ -oximino ketones remarkably increased, as the increase of molar ratio of hydride used to the reactant. The use of 24 moles of $LiAlH_4$ was found to afford the best result in the reduction of the rigid ${\alpha}$-oximino ketones to the corresponding amino alcohols. The yields was not affected by the variation of solvents such as ether, THF and diglyme.

• Bulletin of the Korean Chemical Society
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• 제32권1호
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• pp.291-295
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• 2011

The catalytic enantioselective conjugate addition reaction of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones promoted by chiral bifunctional organocatalysts is described. The treatment of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones afforded the corresponding Michael adducts with high enantioselectivity. The conjugate addition adducts are easily converted to chiral $\gamma$-nitro ketones and $\delta$-keto esters.