JP2006265234A5 - - Google Patents

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JP2006265234A5
JP2006265234A5 JP2006045391A JP2006045391A JP2006265234A5 JP 2006265234 A5 JP2006265234 A5 JP 2006265234A5 JP 2006045391 A JP2006045391 A JP 2006045391A JP 2006045391 A JP2006045391 A JP 2006045391A JP 2006265234 A5 JP2006265234 A5 JP 2006265234A5
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lower alkyl
carbon atoms
alkyl group
hydrogen atom
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Claims (9)

一般式（１）で示されるチオフェン化合物：
Figure 2006265234
 〔式中、Ｒ１は水素原子または炭素数１乃至４の低級アルキル基、Ｒ２は水素原子またはアルコール保護基、Ｒ３は−ＣＯＲ４基である（なお、ここで、Ｒ４は炭素数１乃至４の低級アルキル基を示す。）。但し、Ｒ２及びＲ３が水素原子のとき、Ｒ１は水素原子、メチル基、またはｎ−プロピル基のいずれでもない。〕。 Thiophene compound represented by the general formula (1):
Figure 2006265234
 [Wherein, R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R 2 represents a hydrogen atom or an alcohol protecting group, and R 3 represents a —COR 4 group (where R 4 represents a carbon number) 1 to 4 lower alkyl groups). However, when R 2 and R 3 are hydrogen atoms, R 1 is neither a hydrogen atom, a methyl group nor an n-propyl group. ]. 一般式（２）で示されるチオフェン化合物を、遷移金属触媒の存在下、還元および環化する工程を有する、一般式（３ａ）で示されるカフェオフランまたはその類縁体の製造方法：
Figure 2006265234
 （式中、Ｒ１は水素原子または炭素数１乃至４の低級アルキル基、Ｒ４は炭素数１乃至４の低級アルキル基を示す。） A process for producing a caffeophthalan represented by the general formula (3a) or an analog thereof, comprising a step of reducing and cyclizing the thiophene compound represented by the general formula (2) in the presence of a transition metal catalyst:
Figure 2006265234
 (In the formula, R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and R 4 represents a lower alkyl group having 1 to 4 carbon atoms.) 遷移金属触媒がロジウム触媒である、請求項２に記載の製造方法。   The production method according to claim 2, wherein the transition metal catalyst is a rhodium catalyst. 下式で示される工程Ａ〜Ｄ：
工程Ａ：化合物（４）の水酸基を保護する工程
工程Ｂ：工程Ａで得られる化合物（５）をアシル化する工程
工程Ｃ：工程Ｂで得られる化合物（６）を脱保護する工程、及び
工程Ｄ：工程Ｃで得られる化合物（２）を、遷移金属触媒の存在下で、還元および環化する工程
を含む、一般式（３ａ）で示されるカフェオフランまたはその類縁体の製造方法：
Figure 2006265234
 （式中、Ｒ１は水素原子または炭素数１乃至４の低級アルキル基、Ｒ２’はアルコール保護基、Ｒ４は炭素数１乃至４の低級アルキル基を示す。）。 Steps A to D represented by the following formula:
Step A: Step of protecting the hydroxyl group of Compound (4) Step B: Step of acylating Compound (5) obtained in Step A Step C: Step of deprotecting Compound (6) obtained in Step B, and Step D: A process for producing caffeofloran represented by the general formula (3a) or an analog thereof, comprising a step of reducing and cyclizing the compound (2) obtained in Step C in the presence of a transition metal catalyst:
Figure 2006265234
 (Wherein R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R 2 ′ represents an alcohol protecting group, and R 4 represents a lower alkyl group having 1 to 4 carbon atoms). 4-メチル-6-エチル-2,3-ジヒドロチエノ[2,3c]フラン、4-エチル-6-メチル-2,3-ジヒドロチエノ[2,3c]フラン、および4-エチル-2,3-ジヒドロチエノ[2,3c]フランから選択されるカフェオフラン類縁体。   4-methyl-6-ethyl-2,3-dihydrothieno [2,3c] furan, 4-ethyl-6-methyl-2,3-dihydrothieno [2,3c] furan, and 4-ethyl-2,3-dihydrothieno [2,3c] Caffe offran analogs selected from furan. 下記一般式（７）で示されるチオフェン化合物：
Figure 2006265234
 （式中、Ｒ１は水素原子または炭素数１乃至４の低級アルキル基、Ｒ５は炭素数１乃至４の低級アルキル基を示す）。 A thiophene compound represented by the following general formula (7):
Figure 2006265234
 (Wherein R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and R 5 represents a lower alkyl group having 1 to 4 carbon atoms). 下式に示される化合物（８）を環化する工程を有する、請求項６に記載するチオフェン化合物（７）の製造方法：
Figure 2006265234
 （式中、Ｒ１は水素原子または炭素数１乃至４の低級アルキル基、Ｒ５は炭素数１乃至４の低級アルキル基を示す）。 The manufacturing method of the thiophene compound (7) of Claim 6 which has the process of cyclizing the compound (8) shown by the following Formula:
Figure 2006265234
 (Wherein R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and R 5 represents a lower alkyl group having 1 to 4 carbon atoms). 一般式（３）で示されるカフェオフラン若しくはその類縁体：
Figure 2006265234
 （式中、Ｒ１は水素原子または炭素数１乃至４の低級アルキル基、Ｒ４’は水素原子または炭素数１乃至４の低級アルキル基を示す）、
及び請求項６記載のチオフェン化合物（７）よりなる群から選択される少なくとも１種の化合物を、１０−２〜１０６ｐｐｂの割合で含むことを特徴とする香料組成物。 Café off-run represented by the general formula (3) or an analog thereof:
Figure 2006265234
 (Wherein R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R 4 ′ represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms)
And a fragrance composition comprising at least one compound selected from the group consisting of the thiophene compound (7) according to claim 6 in a ratio of 10 −2 to 10 6 ppb. 一般式（３）で示されるカフェオフラン若しくはその類縁体：
Figure 2006265234
 （式中、Ｒ１は水素原子または炭素数１乃至４の低級アルキル基、Ｒ４’は水素原子または炭素数１乃至４の低級アルキル基を示す）、
及び請求項６記載のチオフェン化合物（７）よりなる群から選択される少なくとも１種の化合物を、１０−３〜１０９ｐｐｂの割合で含むことを特徴とする飲食品。 Café off-run represented by the general formula (3) or an analog thereof:
Figure 2006265234
 (Wherein R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R 4 ′ represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms)
And at least one compound selected from the group consisting of the thiophene compound (7) according to claim 6 at a ratio of 10 −3 to 10 9 ppb.
JP2006045391A 2005-02-22 2006-02-22 NOVEL THIOPHENE COMPOUND, AND PROCESS FOR PRODUCING CAFE OFFRAN OR ITS ANALOGUE USING THE SAME Active JP4617446B2 (en)

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JP2005045014 2005-02-22
JP2006045391A JP4617446B2 (en) 2005-02-22 2006-02-22 NOVEL THIOPHENE COMPOUND, AND PROCESS FOR PRODUCING CAFE OFFRAN OR ITS ANALOGUE USING THE SAME

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JP2006265234A5 true JP2006265234A5 (en) 2007-03-08
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JP2007236260A (en) * 2006-03-08 2007-09-20 Sanei Gen Ffi Inc Tea-containing food and drink additive comprising kahweofuran or its relative body
JP7051527B2 (en) * 2018-03-27 2022-04-11 三栄源エフ・エフ・アイ株式会社 Method for producing caffeoflan or its derivative

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CH527571A (en) * 1968-12-27 1972-09-15 Firmenich & Cie Use of bicyclic compounds as flavoring agents

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