JP4915019B2 - ビナフトール誘導体並びに光学分割及び変換方法 - Google Patents
ビナフトール誘導体並びに光学分割及び変換方法 Download PDFInfo
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- JP4915019B2 JP4915019B2 JP2008029515A JP2008029515A JP4915019B2 JP 4915019 B2 JP4915019 B2 JP 4915019B2 JP 2008029515 A JP2008029515 A JP 2008029515A JP 2008029515 A JP2008029515 A JP 2008029515A JP 4915019 B2 JP4915019 B2 JP 4915019B2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B55/00—Racemisation; Complete or partial inversion
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
上記化学式1〜化学式6の化合物を合成する方法は、いずれにしてもよいが、一般に下記のスキーム等によって合成されることができる。
上記化学式1の化合物は一般に、下記スキーム1によって合成されることができる。
[スキーム1]
(上記スキーム1において、MOMはメトキシメチル(methoxymethyl)基を示し、Bocはt−ブトキシカルボニル(t−butoxy carbonyl)基を示し、PCCはピリジニウムクロロクロメート(pyridinium chlorochromate)を示し、PPAはポリりん酸(polyphosphoric acid)を示す)
[スキーム5]
を共通に含むビナフトール誘導体であって、上記[化学式1]〜[化学式6](上記化学式1〜6中のR1〜R8は各々、
i)−OH、水素またはハロゲンに置換可能な直鎖または分岐鎖アルキル、
ii)−OH、またはハロゲンに置換可能なシクリックアルキル、アルケニル、アルキニル、または
iii)−OH、またはハロゲンに置換可能なアリールである)
からなる群より選択されることを特徴とするビナフトール誘導体を提供する。
[化学式7]
(上記化学式7中のR9〜R11は水素、または1価の有機基(Organic group)、またはハロゲンであり、R12は2価の有機基(Organic group)である)
のラセミアミノアルコール、または下記[化学式8]
[化学式8]
(上記化学式8中のR13〜R15は水素、または1価の有機基である)
のラセミアミノ酸を光学分割(Optical Resolution)する方法を提供する。
[化学式9]
(前記化学式9中のR13〜R15は水素、または1価の有機基である)
のアミノ酸のD−formをL−formに、またはL−formをD−formに光学変換(Optical Transformation)する光学変換方法を提供する。
以下、添付の図面を参照しながら、本発明の好適な実施形態例を詳記する。下記の実施例は説明の目的のためのもので、本発明を限定するものではない。
(S)−1−メトキシメチル−2−ヒドロキシメチル−ビナフトール(化合物13、0.41mmol)に、NaH(11mg、0.46mmol)及び3−(ブロモメチル)ベンズアルデヒド(82mg、0.42mmol)を添加して、DMFで攪拌して化合物14を得た。
[表1] 実施例8(化合物8及び化合物9)及び比較例1におけるアミノアルコールに対するキラル選択性(KR=R−アミノアルコールによるイミン形成定数;KS=S−アミノアルコールによるイミン形成定数)
本発明のビナフトール誘導体を用いたアミノ酸の光学変換程度は次の通り試験した。
[表2]平衡状態でD−アミノ酸/L−アミノ酸の比率(1H NMRの積分比(integration ratio)で測定した)
Claims (6)
- 前記R9〜R11は1価の有機基・前記R12は2価の有機基であって、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のシクリックアルキル、または置換または非置換のアリールであることを特徴とする請求項2に記載の光学分割方法。
- 前記R13〜R15は1価の有機基であって、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のシクリックアルキル、または置換または非置換のアリールであることを特徴とする請求項2に記載の光学分割方法。
- 前記R13〜R15は1価の有機基であって、置換または非置換のアルキル、置換または非置換のアルケニル、置換または非置換のシクリックアルキル、または置換または非置換のアリールであることを特徴とする請求項5に記載の光学変換方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020070072598A KR100870227B1 (ko) | 2007-07-20 | 2007-07-20 | 강력한 수소결합 제공기를 갖는 알라닌 라스메이즈 모방키랄 바이나프톨 유도체 및 이 유도체를 이용한 광학 분할및 변환 방법 |
KR10-2007-0072598 | 2007-07-20 |
Publications (2)
Publication Number | Publication Date |
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JP2009023989A JP2009023989A (ja) | 2009-02-05 |
JP4915019B2 true JP4915019B2 (ja) | 2012-04-11 |
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JP2008029515A Expired - Fee Related JP4915019B2 (ja) | 2007-07-20 | 2008-02-08 | ビナフトール誘導体並びに光学分割及び変換方法 |
Country Status (4)
Country | Link |
---|---|
US (2) | US7847124B2 (ja) |
EP (4) | EP2189433A1 (ja) |
JP (1) | JP4915019B2 (ja) |
KR (1) | KR100870227B1 (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100870227B1 (ko) * | 2007-07-20 | 2008-11-24 | (주)그린포뮬라 | 강력한 수소결합 제공기를 갖는 알라닌 라스메이즈 모방키랄 바이나프톨 유도체 및 이 유도체를 이용한 광학 분할및 변환 방법 |
KR101087498B1 (ko) * | 2008-11-14 | 2011-11-28 | 주식회사 아미노룩스 | 바이나프톨 알데히드 유도체 및 그의 제조방법 |
US8865933B2 (en) | 2009-03-23 | 2014-10-21 | Aminologics Co., Ltd. | Method for obtaining optically pure amino acids |
WO2010120138A2 (ko) * | 2009-04-15 | 2010-10-21 | 이화여자대학교 산학협력단 | 아미노산의 l/d 광학변환 및, 아미노산 및 아미노알코올의 광학분할을 위한 키랄 살리실 알데히드 화합물 및 키랄 나프톨 알데히드 화합물 |
KR20120067586A (ko) | 2010-12-16 | 2012-06-26 | 주식회사 아미노룩스 | 광학적으로 순수한 바이나프톨 유도체 및 그의 제조 방법 |
KR101374569B1 (ko) | 2012-09-06 | 2014-03-20 | 주식회사 아미노로직스 | 광학 아미노산 분리용 하이드록시페닐 바이나프톨 케톤 유도체 및 그 용도 |
KR101497333B1 (ko) * | 2012-12-13 | 2015-03-05 | 연세대학교 산학협력단 | 탈라세믹화를 이용한 광학 활성 아미노산의 제조방법 |
CA2895334C (en) | 2012-12-17 | 2020-12-29 | Hamari Chemicals, Ltd. | Axially chiral n-(2-acylaryl)-2-[5,7-dihydro-6h-dibenzo[c,e]azepin-6-yl]acetamide compound and chirality interconversion method of .alpha.-amino acid using the same |
US10231497B2 (en) * | 2013-06-10 | 2019-03-19 | Voesh Corporation | Skin care mask glove and mask sock |
CN111018911B (zh) * | 2019-12-19 | 2020-12-08 | 西南大学 | 一种手性1,2-二(杂)芳基乙二胺化合物及其制备方法 |
CN113244951B (zh) * | 2021-02-24 | 2022-04-12 | 天津商业大学 | 介孔分子筛负载的催化剂及其应用 |
Family Cites Families (12)
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JPH0714898B2 (ja) | 1988-07-28 | 1995-02-22 | 高砂香料工業株式会社 | 光学活性α−ヒドロキシカルボン酸エステルの製造法 |
JP2580404B2 (ja) | 1991-04-23 | 1997-02-12 | 株式会社環境科学センター | ビナフトール類のラセミ化および光学分割法 |
DE4341605C2 (de) | 1993-12-07 | 1995-10-05 | Degussa | Verfahren zur Herstellung homochiraler Aminoalkohole |
JP3915140B2 (ja) | 1996-07-08 | 2007-05-16 | 日産化学工業株式会社 | ビナフチル化合物及びその製造法 |
JP2000072728A (ja) * | 1998-08-25 | 2000-03-07 | Mitsui Chemicals Inc | 光学活性α−置換−β−アミノケトン誘導体の製造法 |
JP4725757B2 (ja) | 1999-03-24 | 2011-07-13 | 東ソー株式会社 | ビナフトールリン酸誘導体及びその利用 |
JP3631070B2 (ja) * | 1999-11-17 | 2005-03-23 | 独立行政法人科学技術振興機構 | 光学活性含弗素ビナフトール誘導体 |
KR100547958B1 (ko) | 2003-03-10 | 2006-02-01 | 부산대학교 산학협력단 | 키랄 크라운에테르를 기저로한 lc용 키랄 고정상, 이의키랄 칼럼 및 이의 제조방법 |
EP1623971A4 (en) | 2003-04-25 | 2006-11-08 | Toagosei Co Ltd | ASYMMETRIC SYNTHETIC CATALYST BASED ON BRONSTED CHIRAL ACID AND PROCESS FOR ASYMMETRIC SYNTHESIS THEREOF |
JP2005029538A (ja) * | 2003-07-10 | 2005-02-03 | Tokyo Kasei Kogyo Kk | 光学活性ビナフトールの製造法 |
KR100661280B1 (ko) * | 2005-02-01 | 2006-12-26 | 이화여자대학교 산학협력단 | 바이나프톨 유도체, 및 광학적 분할 또는 광학적 변환을위한 그의 용도 |
KR100870227B1 (ko) * | 2007-07-20 | 2008-11-24 | (주)그린포뮬라 | 강력한 수소결합 제공기를 갖는 알라닌 라스메이즈 모방키랄 바이나프톨 유도체 및 이 유도체를 이용한 광학 분할및 변환 방법 |
-
2007
- 2007-07-20 KR KR1020070072598A patent/KR100870227B1/ko active IP Right Grant
-
2008
- 2008-02-07 EP EP10156417A patent/EP2189433A1/en not_active Withdrawn
- 2008-02-07 EP EP10156419A patent/EP2189434A1/en not_active Withdrawn
- 2008-02-07 EP EP10156418A patent/EP2189444A1/en not_active Withdrawn
- 2008-02-07 EP EP08101348A patent/EP2017244B1/en not_active Not-in-force
- 2008-02-08 JP JP2008029515A patent/JP4915019B2/ja not_active Expired - Fee Related
- 2008-02-08 US US12/028,566 patent/US7847124B2/en not_active Expired - Fee Related
-
2010
- 2010-10-26 US US12/912,431 patent/US8193370B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP2017244B1 (en) | 2013-03-27 |
EP2189433A1 (en) | 2010-05-26 |
EP2189434A1 (en) | 2010-05-26 |
US7847124B2 (en) | 2010-12-07 |
JP2009023989A (ja) | 2009-02-05 |
US20090023931A1 (en) | 2009-01-22 |
US8193370B2 (en) | 2012-06-05 |
EP2189444A1 (en) | 2010-05-26 |
EP2017244A3 (en) | 2009-02-11 |
US20110040101A1 (en) | 2011-02-17 |
EP2017244A2 (en) | 2009-01-21 |
KR100870227B1 (ko) | 2008-11-24 |
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