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1.发明授权이미다졸리움염에 고정화된 오스뮴 촉매와 키랄 리간드를 이용한 이웃한 키랄 다이올 화합물의 제조 방법 및 촉매회수 방법 失效使用锇催化剂和固定在咪唑鎓盐上的手性配体制备邻位手性二醇化合物的方法，并回收锇催化剂和手性配体
公开(公告)号：KR100528175B1
公开(公告)日：2005-11-15
申请号：KR1020030024334
申请日：2003-04-17
Applicant: 한국과학기술연구원
IPC: C07C29/74
CPC classification number: Y02P20/584
Abstract: 본 발명은 오스뮴 촉매를 사용하는 비대칭 다이히드록시화반응 (asymmetric dihydroxylation, AD라 약칭함)을 이용하여 올레핀 화합물로부터 이웃한 키랄 다이올(vicinal chiral diol)화합물을 제조하는 방법에 관한 것으로서, 1) 용매에 하기 화학식 1 또는 화학식 2의 키랄 리간드, 하기 화학식 3의 이미다졸리움염, 오스뮴 촉매를 넣고 교반한 후 여기에 보조산화제와 올레핀 화합물을 가하고 교반하는 단계(단계 1); 2) 모든 휘발성 물질을 감압하에서 제거하는 단계(단계 2); 3) 휘발성 물질이 제거된 잔류물을 유기용매로 추출하는 단계(단계 3); 및 4) 추출된 유기 용매층으로부터 이웃한 키랄 다이올 화합물을 분리하는 단계(단계 4)로 이루어지는 오스뮴 촉매를 이용하여 올레핀 화합물로부터 이웃한 키랄 다이올 화합물을 제조하는 방법에 관한 것이다. 본 발명은 오스뮴 촉매와 키랄 리간드를 이미다졸리움염에 고정시킴으로써 고가의 오스뮴 촉매 및 키랄 리간드를 용이하게 회수하고 재사용할 수 있어 매우 경제적이고 유용하며, 광학 순도가 높은 광학활성을 지닌 이웃한 키랄 다이올 화합물을 고수율로 제조할 수 있다.
[화학식 1]
[화학식 2]
(상기 화학식 1과 화학식 2는 각각 퀴니딘과 퀴닌의 히드록시기의 수소원자가 치환된 유도체로서 서로 유사 거울상 이성질체임)
[화학식 3]
(상기 식에서, R
1 , R
2 , R
3 , R
4 , R
5 , n 및 A는 명세서 내에서 정의한 바와 같음)-
公开(公告)号：KR1020050028392A
公开(公告)日：2005-03-23
申请号：KR1020030064579
申请日：2003-09-17
Applicant: 한국과학기술연구원
IPC: C07C2/22
Abstract: A process is provided to produce alkenylated aromatic compounds at a rapid velocity in a high selectivity and a high yield by a Friedel-Crafts alkenylation using a Lewis acid catalyst in the presence of an imidazolium salt. The used Lewis acid catalyst can be separated easily from the produced alkenylated aromatic compounds. The alkenylated aromatic compounds are represented by the formula 1 and are produced by the process containing the steps of: stirring an aromatic compound, an alkyne compound, the imidazolium salt represented by the formula 2, and the Lewis acid catalyst represented by the formula 3: M^n+(B^-)n; separating an organic layer containing the alkenylated aromatic compounds from the imidazolium salt layer containing the Lewis acid catalyst; separating the alkenylated aromatic compounds from the organic layer and refining. In the formula 1, each of R1 and R2 is hydrogen, an alkyl, an aryl and arene is an aromatic compound containing a heteroaromatic compound. In the formula 2, R1 is a C1-C18 alkyl, R2 to R5 are hydrogen or C1-C18 alkyl groups, n is an integer of 1-3, and A is a salt-formable anion. In the formula 3, M is a 3 group, 4 group, 11 group, 12 group, 13 group, 14 group, 15 group element or a lanthanide metal, n is an integer of 2-5, and B is X^-, R6O^- or R7R8N^-.
Abstract translation: 提供了一种通过使用路易斯酸催化剂在咪唑鎓盐存在下，通过Friedel-Crafts烯化反应以快速速度以高选择性和高产率制备烯基化芳族化合物的方法。 使用的路易斯酸催化剂可以容易地从所制备的链烯基芳族化合物中分离出来。 链烯基芳族化合物由式1表示，并通过包括以下步骤的方法制备：将芳族化合物，炔化合物，式2所示的咪唑盐和由式3表示的路易斯酸催化剂： M 1的n +（B ^ - ）n表示 从含有路易斯酸催化剂的咪唑盐层中分离含有烯基化芳族化合物的有机层; 将烯基化芳族化合物与有机层分离并精制。 在式1中，R 1和R 2各自为氢，烷基，芳基和芳烃为含有杂芳族化合物的芳族化合物。 在式2中，R 1为C 1 -C 18烷基，R 2至R 5为氢或C 1 -C 18烷基，n为1-3的整数，A为可成盐阴离子。 式3中，M为3组，4组，11组，12组，13组，14组，15组或镧系金属，n为2-5的整数，B为X ^ - ， R6O - 或R7R8N - 。
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公开(公告)号：KR100476584B1
公开(公告)日：2005-03-17
申请号：KR1020020038928
申请日：2002-07-05
Applicant: 한국과학기술연구원
IPC: C07D207/09
Abstract: 본 발명은 하기 화학식 1로 표시되는 고분자에 결합된 키랄 피롤리디닐(비스포스피노다이아미드) 유도체, 그의 제조방법 및 용도에 관한 것으로, 하기 화합물은 팔라듐과 킬레이트화 반응을 통하여 비대칭 알릴 치환반응 (asymmetric allylic substitution reaction)의 키랄 촉매로 사용되어 광학적 순도가 높은 화합물을 고수율로 제조할 수 있고, 반응 후 용이하게 회수가 가능한 특징이 있다.
화학식 1
(상기식에서,
ⓟ는 모두 명세서내 기재된 바와 같으며, 수소원자(1)과 수소원자(2)는 서로 트랜스의 위치에 있다.)-
公开(公告)号：KR1020040004861A
公开(公告)日：2004-01-16
申请号：KR1020020038928
申请日：2002-07-05
Applicant: 한국과학기술연구원
IPC: C07D207/09
Abstract: PURPOSE: A chiral pyrolidinyl(bisphosphinodiamide) derivative useful for asymmetric allylic substitution reaction is provided. The compound is used as a chiral catalyst in asymmetric allylic substitution reaction to produce a high optical purity compound in higher yield and is easily recovered after the reaction. CONSTITUTION: A chiral pyrolidinyl(bisphosphinodiamide) derivative of the formula(1) useful for asymmetric allylic substitution reaction is provided, wherein P is polystyrene, JANDAJEL(TM) polymer; hydrogen(1) and hydrogen(2) are positioned at a trans position each other; and the compound of the formula(1) comprises mirror image isomers represented by formulas(1a and 1b). A method for preparing the chiral pyrolidinyl(bisphosphinodiamide) derivative of the formula(1) comprises reacting a compound of the formula(2) with a compound of the formula(3), wherein Z is halogen.
Abstract translation: 目的：提供可用于不对称烯丙基取代反应的手性吡咯烷基（二膦基二酰胺）衍生物。 该化合物用作不对称烯丙基取代反应中的手性催化剂以产生更高收率的高光学纯度化合物，并且在反应后容易回收。 构成：提供了可用于不对称烯丙基取代反应的式（1）的手性吡咯烷基（二膦基二酰胺）衍生物，其中P是聚苯乙烯，JANDAJEL TM聚合物; 氢（1）和氢（2）彼此位于反位; 并且式（1）的化合物包括由式（1a和1b）表示的镜像异构体。 制备式（1）的手性吡咯烷基（二膦基二酰胺）衍生物的方法包括使式（2）的化合物与式（3）的化合物反应，其中Z是卤素。
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公开(公告)号：KR100275786B1
公开(公告)日：2001-02-01
申请号：KR1019980008512
申请日：1998-03-13
Applicant: 한국과학기술연구원
IPC: C07G5/00
Abstract: PURPOSE: Provided is a bis-cinchona alkaloid derivative bonded to silicagel support as a useful catalyst for producing vicinal diols by means of asymmetric dihydroxylation with olefin compound. CONSTITUTION: The derivative represented by the formula 3 is prepared by reacting a bis-cinchona alkaloid derivative represented by the formula 1 as a chiral monomer with a mercapto propyl silanized silica gel of the formula 2 under a presence of 2,2'-azobis isobutyronitrile as a radical reaction initiator. In formula 3, Y is quininyl or quinidinyl; X is not existing or represents unsaturated cyclic compound having 4 carbon atoms; when X is not existing, the derivative is coupled to pyridazine as a heterocyclic compound while X is an unsaturated cyclic compound having 4 carbon atoms it is coupled to phthalazine, and R is methoxy, ethoxy or methyl group.
Abstract translation: 目的：提供了与硅胶载体结合的双螯合生物碱衍生物，作为通过用烯烃化合物的不对称二羟基化产生连环二醇的有用催化剂。 构成：由式3表示的衍生物通过在式2,2的偶氮二异丁腈存在下，将式1的双 - 焦虑激素生物碱衍生物作为手性单体与式2巯基丙基硅烷化硅胶反应来制备 作为自由基反应引发剂。 在式3中，Y是奎宁基或奎宁基; X不存在或表示具有4个碳原子的不饱和环状化合物; 当X不存在时，衍生物作为杂环化合物与哒嗪偶联，而X是具有4个碳原子的不饱和环状化合物，其与酞嗪偶合，R是甲氧基，乙氧基或甲基。
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Patent Agency Ranking
公开(公告)号：KR100275785B1
公开(公告)日：2001-02-01
申请号：KR1019980003408
申请日：1998-02-06
Applicant: 한국과학기술연구원
IPC: C07D205/08
Abstract: PURPOSE: Provided are a preparation method of (3R,4S)-hydroxy-4-phenylazetidine-2-one and its intermediate, represented by formula(1), wherein the intermediate is a vital intermediate in the synthesis of taxane based anti-cancer agents. The method provides optically pure compound of the formula(1) in high yield. CONSTITUTION: The method of preparation comprises: reacting trans-cinnamamide derivatives(formula 5) with unsymmetric dihydroxy catalyst to obtain (2R,2S)-2,3-dihydroxy-3-phenylpropionamide derivative(formula 6); halocarboxylating the above compound(formula 6) to prepare (2R,2S)-2-carboxy-3-halo-3-phenylpropionamide derivative(formula 8); reacting the above compound(formula 8) with base in a non protonic solvent to manufacture (3R,4S)-3-carboxy-4-phenylazetidine-2-one derivative(formula 10); reacting the above compound(formula 10) with oxidant in the organic solvent to manufacture (3R,4S)-3-carboxy-4-phenylazetidine-2-one derivative(formula 11); and hydrolyzing number 3 carbon atom of the above compound(formula 11) to manufacture the title compound(formula 1).
Abstract translation: 目的：提供式（1）表示的（3R，4S） - 羟基-4-苯基氮杂环丁烷-2-酮及其中间体的制备方法，其中中间体是合成基于紫杉烷的抗癌药物中的重要中间体 代理商。 该方法以高产率提供式（1）的光学纯的化合物。 构成：制备方法包括：使反式肉桂酰胺衍生物（式5）与不对称二羟基催化剂反应，得到（2R，2S）-2,3-二羟基-3-苯基丙酰胺衍生物（式6）; 卤代羧化上述化合物（式6）以制备（2R，2S）-2-羧基-3-卤代-3-苯基丙酰胺衍生物（式8）; 使上述化合物（式8）与非质子溶剂中的碱反应制备（3R，4S）-3-羧基-4-苯基氮杂环丁烷-2-酮衍生物（式10）。 将上述化合物（式10）与氧化剂在有机溶剂中反应制备（3R，4S）-3-羧基-4-苯基氮杂环丁烷-2-酮衍生物（式11）; 并水解上述化合物（式11）的3个碳原子以制备标题化合物（式1）。
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公开(公告)号：KR100250957B1
公开(公告)日：2000-05-01
申请号：KR1019970080691
申请日：1997-12-31
Applicant: 한국과학기술연구원
IPC: C07D263/10 , C07C227/30
CPC classification number: C07F9/653 , C07B2200/07 , C07C29/143 , C07C33/22
Abstract: PURPOSE: Provided is a bis (ortho-diarylphosphinophenyl)-tetrahydro-bi(1,3-oxazole) compound represented by the formula (1) which is optically pure and can be useful in various reactions including asymmetric hydrosilylation, hydrogenation, cyclopropanation, and alkylation. Also, its preparation method is also provided. CONSTITUTION: A compound represented by the general formula (I) contains (4S, 4'S)2 ,2'-bis(ortho-diarylphosphinophenyl)-4,4',5,5'-tetrahydro-4,4'-bi(1,3-oxazole) compound represented by the formula (Ia) and (4R, 4'R)2 ,2'-bis(ortho-diarylphosphinophenyl)-4,4',5,5'-tetrahydro-4,4'-bi(1,3-oxazole) compound represented by the formula (Ib) that is an optical compound of the compound (Ia), wherein R is aromatic ring such as phenyl or naphthyl.
Abstract translation: 目的：提供由光学纯的式（1）表示的双（邻 - 二芳基膦基苯基） - 四氢 - 双（1,3-恶唑）化合物，可用于各种反应，包括不对称氢化硅烷化，氢化，环丙烷化和 烷基化。 此外，还提供了其制备方法。 构成：由通式（I）表示的化合物含有（4S，4'S）2，2'-双（邻 - 二芳基膦基苯基）-4,4'，5,5'-四氢-4,4'-双（1 （Ⅰa）和（4R，4'R）2,2'-双（邻 - 二芳基膦基苯基）-4,4'，5,5'-四氢-4,4' 由式（Ib）表示的作为化合物（Ia）的光学化合物的双（1,3-恶唑）化合物，其中R是芳环如苯基或萘基。
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8.发明公开
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公开(公告)号：KR1019930003864B1
公开(公告)日：1993-05-14
申请号：KR1019900016699
申请日：1990-10-19
Applicant: 한국과학기술연구원
IPC: C07C53/122 , C07C59/64
CPC classification number: C07D263/22 , C07C51/00 , C07C59/68
Abstract: A process for preparing d-2-(6-methoxy-2-naphthyl)-propionic acid of formula (I) comprises (a) reacting a metal salt of oxazolidinone of formula (II) with 6-methoxy-2-naphthyl acetchloride of formula (III) in THF under nitrogen gas flow; (b) methylating the obtd. [N-(6-methoxy-2-naphthyl)acetyl -oxazolidinone; and (c) reacting the obtd. [N-(2S)-2-(6-methoxy-2-naphthayl-propionyl -oxazolidinone with alkali metal hydroxide in alc. soln. In the formulas, R1= methyl, isopropyl, sec.-butyl, tert,-butyl, benzyl or phenyl; R2=H or phenyl. The cpd. (I) is useful as a nonsteroidal antipyretic analgesic.
Abstract translation: 将式（I）的d-2-（6-甲氧基-2-萘基） - 丙酸制备的方法包括：（a）使式（II）的恶唑烷酮的金属盐与6-（甲氧基-2-萘基） 式（III）的THF溶液; （b）甲基化该药物。 [N-（6-甲氧基-2-萘基）乙酰基 - 恶唑烷酮; 和（c）反应。 [N-（2S）-2-（6-甲氧基-2-萘甲酰基 - 丙酰基 - 恶唑烷酮与碱金属氢氧化物）在式中，R1 =甲基，异丙基，仲丁基，叔丁基， 苄基或苯基; R2 = H或苯基，cpd（I）可用作非甾体解热镇痛药。
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