公开(公告)号：US07671213B2

公开(公告)日：2010-03-02

申请号：US11860980

申请日：2007-09-25

申请人： Makoto Itagaki ,  Katsuhisa Masumoto

发明人： Makoto Itagaki ,  Katsuhisa Masumoto

IPC分类号： C07D263/12

CPC分类号： C07D263/12 ,  C07B2200/07 ,  C07C67/347 ,  C07C215/28 ,  C07C233/18 ,  C07C2601/02 ,  C07C69/747

摘要： Optically active bisoxazoline compounds represented by the general formula (1), a process for producing the compounds, and a process for producing cyclopropanecarboxylic esters by using the same: wherein R1 and R2 are the same and each represents C1-6 alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted phenyl or R1 and R2 are bonded each other together with the carbon atom of oxazoline ring to which they are bonded to form a ring; R3 is substituted or unsubstituted naphthyl; R4 and R5 are the same and each represent hydrogen or C1-6 alkyl, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.

摘要翻译： 由通式（1）表示的光学活性的双恶唑啉化合物，该化合物的制备方法以及通过使用该化合物制备环丙烷羧酸酯的方法：其中R1和R2相同，各自表示C1-6烷基，取代或未取代的 芳烷基或取代或未取代的苯基或R 1和R 2与它们所键合的恶唑啉环的碳原子一起形成环; R3是取代或未取代的萘基; R 4和R 5相同，各自表示氢或C 1-6烷基，或者R 4和R 5与它们所键合的碳原子一起键合形成具有3〜6个碳原子的环烷基环; *表示非对称中心。

公开(公告)号：US07683215B2

公开(公告)日：2010-03-23

申请号：US11860987

申请日：2007-09-25

申请人： Makoto Itagaki ,  Katsuhisa Masumoto

发明人： Makoto Itagaki ,  Katsuhisa Masumoto

IPC分类号： C07C215/04

CPC分类号： C07D263/12 ,  C07B2200/07 ,  C07C67/347 ,  C07C215/28 ,  C07C233/18 ,  C07C2601/02 ,  C07C69/747

摘要： Optically active bisoxazoline compounds represented by the general formula (1), a process for producing the compounds, and a process for producing cyclopropanecarboxylic esters by using the same: wherein R1 and R2 are the same and each represents C1-6 alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted phenyl or R1 and R2 are bonded each other together with the carbon atom of oxazoline ring to which they are bonded to form a ring; R3 is substituted or unsubstituted naphthyl; R4 and R5 are the same and each represent hydrogen or C1-6 alkyl, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.

公开(公告)号：US07709651B2

公开(公告)日：2010-05-04

申请号：US10572391

申请日：2004-09-17

申请人： Makoto Itagaki ,  Katsuhisa Masumoto ,  Ryo Minamida

发明人： Makoto Itagaki ,  Katsuhisa Masumoto ,  Ryo Minamida

IPC分类号： C07F1/08 ,  C07C69/74

CPC分类号： C07C67/347 ,  C07B2200/07 ,  C07C68/06 ,  C07F1/005 ,  C07C69/757 ,  C07C69/96

摘要： A process for producing an optically active cyclopropane compound represented by the formula (4): wherein R3, R4, R5 and R6 are the same or different, and represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, and so on; and R7 represents a C1-6 alkyl group; and * represents an asymmetric carbon atom, which comprises reacting a prochiral olefin represented by the formula (2): wherein R3, R4, R5, and R6 are as described above, with a diazoacetic acid ester represented by the formula (3): N2CHCO2R7  (3) wherein R7 is as defined above, in the presence of an asymmetric copper complex prepared from an optically active cycloalkylidenebisoxazoline compound represented by the formula (1): wherein R1 represents a hydrogen atom, a C1-6 alkyl group, and so on; R2 represents a C1-6 alkyl group and so on; and n represents an integer of 0 to 3; provided that, two R1s may be bonded each other together with the carbon atom to which they are bonded to form a ring; and * represents an asymmetric carbon atom, and a copper compound, is provided.

摘要翻译： 一种制备由式（4）表示的光学活性环丙烷化合物的方法：其中R3，R4，R5和R6相同或不同，表示氢原子，卤素原子，取代或未取代的烷基等 上; 并且R 7表示C 1-6烷基; 和*表示不对称碳原子，其包括使由式（2）表示的前手性烯烃：其中R3，R4，R5和R6如上所述与由式（3）表示的重氮乙酸酯反应：N 2 CHCO 2 R 7 在由式（1）表示的光学活性亚环烷基双恶唑啉化合物制备的不对称铜络合物存在下，其中R 7如上所定义：其中R 1表示氢原子，C 1-6烷基等 ; R2代表C1-6烷基等; n表示0〜3的整数， 条件是两个R 1可以与它们所键合的碳原子相互键合形成环; 和*表示不对称碳原子，并且提供铜化合物。

公开(公告)号：US07288674B2

公开(公告)日：2007-10-30

申请号：US10544494

申请日：2004-02-04

申请人： Makoto Itagaki ,  Katsuhisa Masumoto

发明人： Makoto Itagaki ,  Katsuhisa Masumoto

IPC分类号： C07C61/04 ,  C07D263/10

CPC分类号： C07D263/12 ,  C07B2200/07 ,  C07C67/347 ,  C07C215/28 ,  C07C233/18 ,  C07C2601/02 ,  C07C69/747

摘要： Optically active bisoxazoline compounds represented by the general formula (1), a process for producing the compounds, and a process for producing cyclopropanecarboxylic esters by using the same: wherein R1 and R2 are the same and each represents C1-6 alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted phenyl or R1 and R2 are bonded each other together with the carbon atom of oxazoline ring to which they are bonded to form a ring; R3 is substituted or unsubstituted naphthyl; R4 and R5 are the same and each represent hydrogen or C1-6 alkyl, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.

摘要翻译： 由通式（1）表示的光学活性的双恶唑啉化合物，该化合物的制备方法以及使用该化合物制备环丙烷羧酸酯的方法：其中R 1和R 2， SUP>相同，各自表示C 1-6烷基，取代或未取代的芳烷基或取代或未取代的苯基或R 1和R 2 O 2 >与它们所键合的恶唑啉环的碳原子一起形成环; R 3是取代或未取代的萘基; R 4和R 5是相同的，并且各自表示氢或C 1-6烷基，或R 4， R 5和它们所连接的碳原子一起形成具有3〜6个碳原子的环烷基环; *表示非对称中心。

公开(公告)号：US07612227B2

公开(公告)日：2009-11-03

申请号：US10590991

申请日：2005-03-22

申请人： Katsuhisa Masumoto ,  Makoto Itagaki

发明人： Katsuhisa Masumoto ,  Makoto Itagaki

IPC分类号： C07C67/02

CPC分类号： C07C67/08 ,  C07C67/58 ,  C07C69/007 ,  C07C69/145

摘要： The present invention relates to a method for producing 3-methyl-2-butenyl acetate which comprises reacting 3-methyl-2-buten-1-ol with acetic anhydride in the presence of an inorganic base catalyst and a method for producing purified 3-methyl-2-butenyl acetate which comprises subjecting crude 3-methyl-2-butenyl acetate to a step (A) of contacting it with an aqueous solution of an alkali metal hydrogen sulfite, or a step (B) of contacting it with an aqueous solution of a base, or both steps (A) and (B).

摘要翻译： 本发明涉及一种在无机碱催化剂存在下使3-甲基-2-丁烯-1-醇与乙酸酐反应的乙酸3-甲基-2-丁烯酯的制备方法， 包括使乙酸3-甲基-2-丁烯酯进行与碱金属亚硫酸氢钠水溶液接触的步骤（A）的步骤（B）或使其与水 碱的溶液，或步骤（A）和（B）两者。

公开(公告)号：US20080275268A1

公开(公告)日：2008-11-06

申请号：US10590991

申请日：2005-03-22

申请人： Katsuhisa Masumoto ,  Makoto Itagaki

发明人： Katsuhisa Masumoto ,  Makoto Itagaki

IPC分类号： C07C67/08

CPC分类号： C07C67/08 ,  C07C67/58 ,  C07C69/007 ,  C07C69/145

摘要： The present invention relates to a method for producing 3-methyl-2-butenyl acetate which comprises reacting 3-methyl-2-buten-1-ol with acetic anhydride in the presence of an inorganic base catalyst and a method for producing purified 3-methyl-2-butenyl acetate which comprises subjecting crude 3-methyl-2-butenyl acetate to a step (A) of contacting it with an aqueous solution of an alkali metal hydrogen sulfite, or a step (B) of contacting it with an aqueous solution of a base, or both steps (A) and (B).

摘要翻译： 本发明涉及一种在无机碱催化剂存在下使3-甲基-2-丁烯-1-醇与乙酸酐反应的乙酸3-甲基-2-丁烯酯的制备方法， 包括使乙酸3-甲基-2-丁烯酯进行与碱金属亚硫酸氢钠水溶液接触的步骤（A）的步骤（B）或使其与水 碱的溶液，或步骤（A）和（B）两者。

公开(公告)号：US20080076941A1

公开(公告)日：2008-03-27

申请号：US11860987

申请日：2007-09-25

申请人： Makoto ITAGAKI ,  Katsuhisa Masumoto

发明人： Makoto ITAGAKI ,  Katsuhisa Masumoto

IPC分类号： C07C215/04

CPC分类号： C07D263/12 ,  C07B2200/07 ,  C07C67/347 ,  C07C215/28 ,  C07C233/18 ,  C07C2601/02 ,  C07C69/747

摘要： Optically active bisoxazoline compounds represented by the general formula (1), a process for producing the compounds, and a process for producing cyclopropanecarboxylic esters by using the same: wherein R1 and R2 are the same and each represents C1-6 alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted phenyl or R1 and R2 are bonded each other together with the carbon atom of oxazoline ring to which they are bonded to form a ring; R3 is substituted or unsubstituted naphthyl; R4 and R5 are the same and each represent hydrogen or C1-6 alkyl, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.

公开(公告)号：US20080076931A1

公开(公告)日：2008-03-27

申请号：US11860980

申请日：2007-09-25

申请人： Makoto ITAGAKI ,  Katsuhisa Masumoto

发明人： Makoto ITAGAKI ,  Katsuhisa Masumoto

IPC分类号： C07D263/12

CPC分类号： C07D263/12 ,  C07B2200/07 ,  C07C67/347 ,  C07C215/28 ,  C07C233/18 ,  C07C2601/02 ,  C07C69/747

摘要： Optically active bisoxazoline compounds represented by the general formula (1), a process for producing the compounds, and a process for producing cyclopropanecarboxylic esters by using the same: wherein R1 and R2 are the same and each represents C1-6 alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted phenyl or R1 and R2 are bonded each other together with the carbon atom of oxazoline ring to which they are bonded to form a ring; R3 is substituted or unsubstituted naphthyl; R4 and R5 are the same and each represent hydrogen or C1-6 alkyl, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.

摘要翻译： 由通式（1）表示的光学活性的双恶唑啉化合物，该化合物的制备方法以及使用该化合物制备环丙烷羧酸酯的方法：其中R 1和R 2， SUP>相同，各自表示C 1-6烷基，取代或未取代的芳烷基或取代或未取代的苯基或R 1和R 2 O 2 >与它们所键合的恶唑啉环的碳原子一起形成环; R 3是取代或未取代的萘基; R 4和R 5是相同的，并且各自表示氢或C 1-6烷基，或R 4， R 5和它们所连接的碳原子一起形成具有3〜6个碳原子的环烷基环; *表示非对称中心。

公开(公告)号：US20070032659A1

公开(公告)日：2007-02-08

申请号：US10572391

申请日：2004-09-17

申请人： Makoto Itagaki ,  Katsuhisa Masumoto ,  Ryo Minamida

发明人： Makoto Itagaki ,  Katsuhisa Masumoto ,  Ryo Minamida

IPC分类号： C07F1/08 ,  C07C69/74

CPC分类号： C07C67/347 ,  C07B2200/07 ,  C07C68/06 ,  C07F1/005 ,  C07C69/757 ,  C07C69/96

摘要： A process for producing an optically active cyclopropane compound represented by the formula (4): wherein R3, R4, R5 and R6 are the same or different, and represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, and so on; and R7 represents a C1-6 alkyl group; and * represents an asymmetric carbon atom, which comprises reacting a prochiral olefin represented by the formula (2): wherein R3, R4, R5, and R6 are as described above, with a diazoacetic acid ester represented by the formula (3): N2CHCO2R7  (3) wherein R7 is as defined above, in the presence of an asymmetric copper complex prepared from an optically active cycloalkylidenebisoxazoline compound represented by the formula (1): wherein R1 represents a hydrogen atom, a C1-6 alkyl group, and so on; R2 represents a C1-6 alkyl group and so on; and n represents an integer of 0 to 3; provided that, two R1s may be bonded each other together with the carbon atom to which they are bonded to form a ring; and * represents an asymmetric carbon atom, and a copper compound, is provided.

摘要翻译： 一种制备由式（4）表示的光学活性环丙烷化合物的方法：其中R 3，R 4，R 5和R 5， SUP> 6相同或不同，表示氢原子，卤素原子，取代或未取代的烷基等; R 7表示C 1-6烷基; 和*表示不对称碳原子，其包括使由式（2）表示的前手性烯烃：其中R 3，R 4，R 5， 和＆lt; 6＆gt;如上所述，用式（3）表示的重氮乙酸酯：<？in-line-formula description =“In-line Formulas”end =“lead （3）<？in-line-formula description =“In-line Formulas”end =“In-line formula”end =“In-line formula”end = 在由式（1）表示的光学活性亚环烷基双恶唑啉化合物制备的不对称铜络合物存在下，其中R 7定义如上所述：其中R 1， / SUP>表示氢原子，C 1-6烷基等; R 2表示C 1-6烷基等; n表示0〜3的整数， 条件是两个R 1可以与它们所键合的碳原子一起形成环; 和*表示不对称碳原子，并且提供铜化合物。

公开(公告)号：US20060149077A1

公开(公告)日：2006-07-06

申请号：US10544494

申请日：2004-02-04

申请人： Makoto Itagaki ,  Katsuhisa Masumoto

发明人： Makoto Itagaki ,  Katsuhisa Masumoto

IPC分类号： C07D413/02

CPC分类号： C07D263/12 ,  C07B2200/07 ,  C07C67/347 ,  C07C215/28 ,  C07C233/18 ,  C07C2601/02 ,  C07C69/747

摘要： Optically active bisoxazoline compounds represented by the general formula (1), a process for producing the compounds, and a process for producing cyclopropanecarboxylic esters by using the same: wherein R1 and R2 are the same and each represents C1-6 alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted phenyl or R1 and R2 are bonded each other together with the carbon atom of oxazoline ring to which they are bonded to form a ring; R3 is substituted or unsubstituted naphthyl; R4 and R5 are the same and each represent hydrogen or C1-6 alkyl, or R4 and R5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.

摘要翻译： 由通式（1）表示的光学活性的双恶唑啉化合物，该化合物的制备方法以及使用该化合物制备环丙烷羧酸酯的方法：其中R 1和R 2， SUP>相同，各自表示C 1-6烷基，取代或未取代的芳烷基或取代或未取代的苯基或R 1和R 2 O 2 >与它们所键合的恶唑啉环的碳原子一起形成环; R 3是取代或未取代的萘基; R 4和R 5是相同的，并且各自表示氢或C 1-6烷基，或R 4， R 5和它们所连接的碳原子一起形成具有3〜6个碳原子的环烷基环; *表示非对称中心。