WO2021085482A1 - Composé et son procédé de production - Google Patents

Composé et son procédé de production Download PDF

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WO2021085482A1
WO2021085482A1 PCT/JP2020/040461 JP2020040461W WO2021085482A1 WO 2021085482 A1 WO2021085482 A1 WO 2021085482A1 JP 2020040461 W JP2020040461 W JP 2020040461W WO 2021085482 A1 WO2021085482 A1 WO 2021085482A1
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group
compound
carbon atoms
general formula
alkyl group
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PCT/JP2020/040461
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Japanese (ja)
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正安 五十嵐
竹志 野澤
朋浩 松本
不二夫 八木橋
佐藤　一彦
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国立研究開発法人産業技術総合研究所
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Priority to JP2021553657A priority Critical patent/JP7360205B2/ja
Publication of WO2021085482A1 publication Critical patent/WO2021085482A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring

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  • the present invention relates to a compound and a method for producing the same.
  • the present application claims priority based on Japanese Patent Application No. 2019-199334 filed in Japan on October 31, 2019, the contents of which are incorporated herein by reference.
  • a group of siloxane compounds having a cage-shaped skeleton which can be regarded as a condensate of orthosilicic acid or a derivative thereof, are promising in various fields as functional silicon materials. Has been done.
  • a compound represented by the following formula (91) is used as a raw material by a synthetic route shown below, and a compound represented by the following formula (91) (in the present specification). Has been obtained (sometimes referred to as "Compound (91)”) (see Non-Patent Document 1).
  • Non-Patent Document 1 discloses compound (91) as a novel cage-type siloxane compound and a method for producing the compound (91), but at present, it cannot be said that the search for a cage-type siloxane compound has been sufficiently performed. , A new cage-type siloxane compound and a method for producing the same have been desired.
  • An object of the present invention is to provide a novel cage-type siloxane compound and a method for producing the same.
  • the present invention has the following general formula (2):
  • n is an integer of 1 to 4; R 4 is an alkyl group, an alkenyl group or an aryl group which may have a hydrogen atom or a substituent, and n is 2 or more.
  • N R 4s may be the same or different from each other, provided that at least one R 4 is the alkyl group, alkenyl group or aryl group and three or more R 4s are said alkyl groups.
  • R 5 when an alkenyl group or an aryl group, these groups, except at least one mutual coupling to the may form a ring; R 5 also have a hydrogen atom, or a substituent When it is a good alkyl group, alkenyl group or aryl group and n is 2 or less, the 4-n R 5s may be the same or different from each other, and two or more R 5s are the alkyl group, the alkenyl group. When it is a group or an aryl group, these groups may be bonded to each other to form a ring.)
  • Z 4 is a hydrogen atom or a general formula "-Si (OR 4) n-1 (R 5) 4-n " is a group represented by, (2p 1 +6) number of Z 4 are mutually It may be the same or different, provided that one or more Z 4 is a group represented by the general formula "-Si (oR 4) n-1 (R 5) 4-n "; n, p 1 , R 4 and R 5 are the same as above, and when n is 3 or more, n-1 R 4s may be the same or different from each other, and 2 or more R 4s.
  • alkyl group, an alkenyl group or an aryl group these groups may form a ring with each other, when n is 2 or less, the 4-n-number of R 5, identical to each other But it may be different, two or more R 5 is the alkyl group, alkenyl group or if an aryl group, these groups may form a ring with each other.)
  • a method for producing a compound for obtaining the compound represented by is a method for producing a compound for obtaining the compound represented by.
  • Z 40 is a hydrogen atom or a group represented by the general formula "-Si (OR 40 ) m-1 (R 50 ) 4-m". (2p 1 + 6) Z 40s may be the same or different from each other, except that one or more Z 40s are the above general formula "-Si (OR 40 ) m-1 (R 50 ) 4". It is a group represented by "-m "; m is an integer of 2 to 4; R 40 is an alkyl group, an alkenyl group or an aryl group which may have a hydrogen atom or a substituent.
  • the m-1 R 40s may be the same or different from each other, and when two or more R 40s are the alkyl group, alkenyl group or aryl group, these groups are mutual. It may be bonded to to form a ring;
  • R 50 is an alkyl group, an alkenyl group or an aryl group which may have a hydrogen atom or a substituent, and when m is 2, two of them are used.
  • R 50s may be the same or different from each other, and when two R 50s are the alkyl group, alkenyl group or aryl group, these groups may be bonded to each other to form a ring.
  • the R 40 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.
  • the R 50 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms
  • m is 2
  • the above-mentioned formula "-Si (OR 40) m-1 (R 50) 4-m " two R 50 in may be the same or different, may be a compound.
  • the R 40 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
  • the R 50 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms
  • m is 2
  • the above-mentioned formula "-Si (OR 40) m-1 (R 50) 4-m " two R 50 in may be the same or different, may be a compound.
  • the present invention has the following general formula (4021):
  • Z 41 is a hydrogen atom or a group represented by the general formula "-Si (OR 41 ) m-1 (R 51 ) 4-m ", and the eight Z 41s are the same or different from each other.
  • one or more Z 41s are groups represented by the general formula "-Si (OR 41 ) m-1 (R 51 ) 4-m "; m is 2
  • R 41 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and m is 3 or more.
  • M-1 R 41s may be the same or different from each other, and when two or more R 41s are the alkyl group, alkenyl group or aryl group, these groups are bonded to each other to form a ring.
  • R 51 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms, and when m is 2, 2
  • the R 51s may be the same or different from each other, and when the two R 51s are the alkyl group, alkenyl group or aryl group, these groups may be bonded to each other to form a ring.
  • a novel cage-type siloxane compound and a method for producing the same are provided.
  • n is an integer of 1 to 4; R 4 is an alkyl group, an alkenyl group or an aryl group which may have a hydrogen atom or a substituent, and n is 2 or more.
  • N R 4s may be the same or different from each other, provided that at least one R 4 is the alkyl group, alkenyl group or aryl group and three or more R 4s are said alkyl groups.
  • R 5 when an alkenyl group or an aryl group, these groups, except at least one mutual coupling to the may form a ring; R 5 also have a hydrogen atom, or a substituent When it is a good alkyl group, alkenyl group or aryl group and n is 2 or less, the 4-n R 5s may be the same or different from each other, and two or more R 5s are the alkyl group, the alkenyl group. When it is a group or an aryl group, these groups may be bonded to each other to form a ring.)
  • compound (5) By reacting with a compound represented by (in the present specification, it may be referred to as "compound (5)"), the following general formula (4):
  • Z 4 is a hydrogen atom or a general formula "-Si (OR 4) n-1 (R 5) 4-n " is a group represented by, (2p 1 +6) number of Z 4 are mutually It may be the same or different, provided that one or more Z 4 is a group represented by the general formula "-Si (oR 4) n-1 (R 5) 4-n "; n, p 1 , R 4 and R 5 are the same as above, and when n is 3 or more, n-1 R 4s may be the same or different from each other, and 2 or more R 4s.
  • a cage-type siloxane compound can be produced.
  • the target compound (4) will be described.
  • Compound (4) is represented by the general formula (4).
  • p 1 is to define the size of the cage of the compound (4) is 0, 1 or 2. That is, the compound (4) when p 1 is 0 is represented by the following general formula (41) (in the present specification, this compound may be referred to as “compound (41)”), and p 1 Compound (4) when is 1 is represented by the following general formula (42) (in the present specification, this compound may be referred to as “compound (42)”), and p 1 is 2.
  • the compound (4) in the case is represented by the following general formula (43) (in the present specification, this compound may be referred to as "compound (43)").
  • Z 4 is a hydrogen atom (-H) or a group represented by the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n".
  • R 4 is an alkyl group, an alkenyl group or an aryl group which may have a hydrogen atom or a substituent.
  • the alkyl group for R 4 may be any of linear, branched and cyclic.
  • carbon atoms in straight chain or branched chain of the alkyl group is not particularly limited, is preferably 1 to 20.
  • Examples of such a linear or branched alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
  • n-pentyl group isopentyl group, neopentyl group, tert-pentyl group, 1-methylbutyl group, n-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 2,2-dimethylbutyl group, 2,3- Dimethylbutyl group, n-heptyl group, 2-methylhexyl group, 3-methylhexyl group, 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3-dimethyl Pentyl group, 3-ethylpentyl group, 2,2,3-trimethylbutyl group, n-octyl group, isooctyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadec
  • the alkyl group of cyclic may be either monocyclic or polycyclic.
  • the number of carbon atoms of the cyclic alkyl group is not particularly limited as long as it is 3 or more, but it is preferably 3 to 20.
  • Examples of the cyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a norbornyl group, an isobornyl group, a 1-adamantyl group and a 2-.
  • the cyclic alkyl group preferably has 3 to 15 carbon atoms, and may be, for example, any of 3 to 10 and 3 to 6, or 5 to 15 and 5 to 10. There may be.
  • the alkyl group for R 4 is a linear or branched chain structure, or may be a cyclic structure, it is mixed.
  • Examples of the alkyl group in which such a chain structure and a cyclic structure are mixed include the above-mentioned linear or branched chain such as a cyclopentylmethyl group, a 1-cyclopentylethyl group, a cyclohexylmethyl group, and a 1-cyclohexylethyl group.
  • Examples thereof include a group having a structure in which one or more hydrogen atoms in the above-mentioned cyclic alkyl group are substituted with the above-mentioned linear or branched alkyl group.
  • the number of carbon atoms of the alkyl group in which the chain structure and the cyclic structure are mixed is not particularly limited as long as it is 4 or more, but is preferably 4 to 25, and may be, for example, 6 to 15.
  • the alkenyl group for R 4 may be any of linear, branched and cyclic.
  • the position of the double bond between carbon atoms is not particularly limited.
  • carbon atoms in straight chain or branched chain of the alkenyl group is not particularly limited, is preferably 2-20.
  • Examples of such a linear or branched alkenyl group include a vinyl group (ethenyl group), an allyl group (2-propenyl group, allyl group), a 3-butenyl group, a 2-butenyl group, and a pentenyl group. Examples thereof include a hexenyl group, a heptenyl group, and an octenyl group.
  • the linear or branched alkenyl group preferably has 2 to 10 carbon atoms, and may be, for example, any of 2 to 6 and 2 to 3.
  • the alkenyl group of cyclic may be either monocyclic or polycyclic.
  • the number of carbon atoms of the cyclic alkenyl group is not particularly limited as long as it is 3 or more, but it is preferably 3 to 20.
  • Examples of the cyclic alkenyl group include a cyclopropenel group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group and the like.
  • the cyclic alkenyl group preferably has 3 to 15 carbon atoms, and may be, for example, any of 3 to 10 and 3 to 6, or 5 to 15 and 5 to 10. There may be.
  • the alkenyl group for R 4 is a linear or branched chain structure, or may be a cyclic structure, are mixed.
  • the carbon number of the alkenyl group in which the chain structure and the cyclic structure are mixed is not particularly limited as long as it is 4 or more, but is preferably 4 to 25, and may be, for example, 6 to 15.
  • R 4 aryl group may be either monocyclic and polycyclic.
  • the aryl group preferably has 6 to 20 carbon atoms, and examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an o-tolyl group, an m-tolyl group, and p-. tolyl group, xylyl group (dimethylphenyl group) can be mentioned, further, one or more hydrogen atoms of these aryl groups, the aryl group, or a structure substituted with an alkyl group in R 4 A group having is also mentioned.
  • the aryl group having these substituents preferably has 6 to 20 carbon atoms.
  • the aryl group preferably has 6 to 12 carbon atoms.
  • the alkyl group, alkenyl group and aryl group may have a substituent.
  • an alkyl group, an alkenyl group and an aryl group has a substituent, unless otherwise stated, one or more constitute these groups It means that the hydrogen atom of is substituted with a group other than the hydrogen atom.
  • the term "group" includes not only an atomic group formed by bonding a plurality of atoms but also one atom, unless otherwise specified.
  • methylene group, an oxygen atom, an alkyl group having a structure substituted with a carbonyl group, or an oxycarbonyl group alkyl group in, for example, those similar to the aforementioned alkyl group in R 4.
  • substitution of a methylene group with a substituent in the above-mentioned "alkyl group having a structure in which the methylene group is substituted with an oxygen atom, a carbonyloxy group, or an oxycarbonyl group".
  • the position is not particularly limited, and the number of substituents may be 1 or 2 or more. Further, when the number of substituents is 2 or more, these substituents may be the same as each other or may be different from each other.
  • R 5 is a hydrogen atom, or an optionally substituted alkyl group, an alkenyl group or an aryl group.
  • the alkyl group, alkenyl group and aryl group in R 5 are the same as the alkyl group, alkenyl group and aryl group in R 4 described above. However, the alkyl group, alkenyl group and aryl group in R 4 and the alkyl group, alkenyl group and aryl group in R 5 are set independently.
  • n is an integer of 1 to 4 (1, 2, 3 or 4).
  • R 4 of formula "-Si (OR 4) n-1 (R 5) 4-n " (n-1) in (2 or 3) can be the same or different from each other You may be. That, n-1 pieces of R 4 may all be the same, may be different, all may be the same part only.
  • n 2 or more, of the general formula "-Si (OR 4) n-1 (R 5) 4-n " (n-1) R 4 in which at least one (one, two or 3) may be an alkyl group, an alkenyl group or an aryl group which may have a substituent.
  • n 3 or more and is represented by the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n ", two or more (two or three) R 4s are the alkyl.
  • R 4s are the alkyl.
  • these groups alkyl group, alkenyl group or aryl group
  • O oxygen atom
  • a ring may be formed together with the silicon atom (Si).
  • the bonding position of R 4 is not particularly limited.
  • the bond position may be a carbon atom at the end of the chain structure or a non-terminal carbon atom.
  • the alkyl group, alkenyl group or aryl group has the substituent, the substituent does not serve as the bond position when forming a ring.
  • the number of binding sites of R 4 when forming the ring may be a 1, it may be two or more. That is, the ring may be either monocyclic or polycyclic.
  • R 5 is of the general formula 4-n-number of "-Si (OR 4) n-1 (R 5) 4-n " in (2 or 3), are identical to or different from each other You may be. That, 4-n-number of R 5 may all be the same, may be different, all may be the same part only.
  • n 2 or less and is represented by the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n ", two or more (two or three) R 5s are the alkyl.
  • R 5s are the alkyl.
  • these groups alkyl group, alkenyl group or aryl group
  • Si silicon atom
  • the bonding position of R 5 is not particularly limited.
  • the bond position may be a carbon atom at the end of the chain structure or a non-terminal carbon atom.
  • the alkyl group, alkenyl group or aryl group has the substituent, the substituent does not serve as the bond position when forming a ring.
  • the number of binding sites in the case of, R 5 forming the ring may be a 1, it may be two or more. That is, the ring may be either monocyclic or polycyclic.
  • R 4 is a hydrogen atom, (linear or branched alkyl group having 1 to 20 carbon atoms, cyclic alkyl group having 3 to 20 carbon atoms) alkyl groups having 1 to 20 carbon atoms, 20 (A linear or branched alkenyl group having 2 to 20 carbon atoms, a cyclic alkenyl group having 3 to 20 carbon atoms) or an aryl group having 6 to 20 carbon atoms is preferable, and n is 3 In the case of the above (3 or 4), n-1 (2 or 3) R 4 in the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n" is , They may be the same or different from each other. In such R 4, the alkyl, alkenyl or aryl group may have a substituent.
  • R 4 is a hydrogen atom, (linear or branched alkyl group having 1 to 6 carbon atoms, cyclic alkyl group having 3 to 6 carbon atoms) alkyl group having 1 to 6 carbon atoms, 2 to 6 carbon atoms (A linear or branched alkenyl group having 2 to 6 carbon atoms, a cyclic alkenyl group having 3 to 6 carbon atoms) or an aryl group having 6 to 12 carbon atoms is more preferable.
  • n-1 (2 or 3) Rs in the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n" 4 may be the same as or different from each other.
  • the alkyl, alkenyl or aryl group may have a substituent.
  • R 5 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms (a linear or branched alkyl group having 1 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms), and 2 to 20 carbon atoms.
  • a linear or branched alkenyl group having 2 to 20 carbon atoms, a cyclic alkenyl group having 3 to 20 carbon atoms) or an aryl group having 6 to 20 carbon atoms is preferable, and n is 2.
  • R 5 in the general formula "-Si (oR 4) n-1 (R 5) 4-n " 4-n-number in (two or three) of , They may be the same or different from each other.
  • R 5 the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 5 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms (a linear or branched alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms), and an alkyl group having 2 to 6 carbon atoms.
  • a linear or branched alkenyl group having 2 to 6 carbon atoms, a cyclic alkenyl group having 3 to 6 carbon atoms) or an aryl group having 6 to 12 carbon atoms is more preferable. If it is 2 or less (1 or 2), R 5 in the general formula "-Si (oR 4) n-1 (R 5) 4-n " 4-n-number in the (2 or 3) May be the same or different from each other. In such R 5, the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 4 and R 5 are the above-mentioned preferable ones.
  • R 4 has a hydrogen atom, an alkyl group having 1 to 20 carbon atoms (a linear or branched alkyl group having 1 to 20 carbon atoms, and an alkyl group having 3 to 20 carbon atoms). Cyclic alkyl group), alkenyl group having 2 to 20 carbon atoms (linear or branched alkenyl group having 2 to 20 carbon atoms, cyclic alkenyl group having 3 to 20 carbon atoms) or alkenyl group having 6 to 20 carbon atoms.
  • R 4 of (or 3) may be the same as or different from each other, and R 5 is a hydrogen atom and an alkyl group having 1 to 20 carbon atoms (a linear or branched alkyl group having 1 to 20 carbon atoms).
  • Cyclic alkyl group having 3 to 20 carbon atoms Alkyl group having 2 to 20 carbon atoms (Linear or branched alkenyl group having 2 to 20 carbon atoms, Cyclic alkenyl group having 3 to 20 carbon atoms)
  • n is 2 or less (1 or 2)
  • R 5 of the 4-n-number may be the same or different, it can be listed.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 4 has a hydrogen atom, an alkyl group having 1 to 6 carbon atoms (a linear or branched alkyl group having 1 to 6 carbon atoms, and an alkyl group having 3 to 6 carbon atoms). Cyclic alkyl group), alkenyl group having 2 to 6 carbon atoms (linear or branched alkenyl group having 2 to 6 carbon atoms, cyclic alkenyl group having 3 to 6 carbon atoms) or alkenyl group having 6 to 12 carbon atoms. When it is an aryl group and n is 3 or more (3 or 4), n-1 (2) in the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n ".
  • number of R 4 may be the same or different from each other, it is R 5, a hydrogen atom, a linear or branched alkyl of 1-6 alkyl group (having a carbon number of 1 to 6 carbon atoms Group, cyclic alkyl group having 3 to 6 carbon atoms), alkenyl group having 2 to 6 carbon atoms (linear or branched alkenyl group having 2 to 6 carbon atoms, cyclic alkenyl group having 3 to 6 carbon atoms) ) Or an aryl group having 6 to 12 carbon atoms, and n is 2 or less (1 or 2), in the above general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n ". the R 5 of the 4-n-number (two or three) of, or be the same or different, can be listed.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • (2p 1 + 6) that is, 6 when p 1 is 0, 8 when p 1 is 1, and 10 when p 1 is 2).
  • Z 4s may be the same or different from each other. That, (2p 1 +6) number of Z 4 may all be the same, may be different, all may be the same part only.
  • Compound (2) is represented by the general formula (2).
  • P 1 of the general formula (2) in is the same as p 1 in the general formula (4).
  • Compound (2) can be produced, for example, by the method described in International Publication No. 2018/193732.
  • a compound that does not contain hydrated water can be prepared by appropriately selecting the operation (for example, washing conditions, removal conditions, purification conditions, etc.) at the time of its production.
  • the operation for example, washing conditions, removal conditions, purification conditions, etc.
  • Compound (2) may not contain a molecule of a solvent component, or may contain a molecule of a solvent component other than water.
  • the solvent component include N, N-dimethylacetamide (DMAc) and the like.
  • DMAc N, N-dimethylacetamide
  • the compound (2) containing a molecule of DMAc is an example of a preferable compound (2) which is easy to produce and does not contain hydrated water.
  • the number of molecules of the solvent component contained in one molecule of the compound (2) can be adjusted according to the operating conditions at the time of producing the compound (2).
  • the number of molecules of DMAc contained in one molecule of the compound (2) may be, for example, any one of 1 to 20, but this is an example.
  • Compound (5) is represented by the general formula (5).
  • Monovalent group having a compound (5) a group represented by silicon atoms single formula bound to the "R 4 O-'in is removed structure, Z 4 in the compound (4) It is the same as the group represented by the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n" in.
  • R 4 and R 5 are n in the general formula (4), and R 4 and R 5 the same.
  • n pieces R 4 of may be the same or different from each other. Ie, n pieces of R 4 may all be the same, may be different, all may be the same part only. However, in the general formula (5), at least one (1, 2, 3, or 4) R 4 is the alkyl group, alkenyl group, or aryl group.
  • R 4 is the alkyl group, when the alkenyl group or an aryl group, these groups (alkyl group, an alkenyl group or an aryl group) is at least one Except for (1 or 2), they are bonded to each other to form a ring together with the oxygen atom (O) to which these groups are bonded and the silicon atom (Si) to which the oxygen atom is bonded. May be.
  • the three R 4 is the alkyl group, if an alkenyl group or an aryl group, two of these groups may be bonded to each other to form the ring
  • four R 4 is the When it is an alkyl group, an alkenyl group or an aryl group, two or three of these groups may be bonded to each other to form the ring.
  • the general formula in the compound (4) in a "-Si (OR 4) n-1 (R 5) 4-n " group represented by two or more R 4 are bonded to each other It is the same as the ring which may be formed.
  • the silicon atom in the group represented by the above-mentioned general formula “-Si (OR 4 ) n-1 (R 5 ) 4-n ” is an alkoxy group or an alkenyloxy group.
  • a compound having a structure bonded to an aryloxy group can be mentioned.
  • Compound (4) is obtained by reacting compound (2) with compound (5).
  • the compound (5) to be subjected to the reaction may be only one kind or two or more kinds, and may be appropriately selected depending on the structure of the target compound (4). When two or more compounds (5) are used, their combinations and ratios can be appropriately adjusted according to the intended purpose.
  • the amount of compound (5) used can be appropriately adjusted according to the structure of the target compound (4) and the like.
  • the amount of the compound (5) used is the number of groups represented by the general formula "-Si (OR 4 ) n-1 (R 5 ) 4-n" in the target compound (4). It can be adjusted accordingly.
  • the amount of the compound (5) is, when the relative amount of the compound (2) is 1 to 2 times molar quantity, the formula in one molecule " A compound (4) having 1 to 2 groups represented by "-Si (OR 4 ) n-1 (R 5 ) 4-n” is preferably obtained.
  • the amount of the compound (5) is, relative to the amount of the compound (2), when it is 3-4 times the molar amount, the formula in one molecule " A compound (4) having 3 to 4 groups represented by "-Si (OR 4 ) n-1 (R 5 ) 4-n” is preferably obtained.
  • the amount of the compound (5) is, relative to the amount of the compound (2), when it is 5 to 6 times molar amount, the formula in one molecule " A compound (4) having 5 to 6 groups represented by "-Si (OR 4 ) n-1 (R 5 ) 4-n" is preferably obtained.
  • the general formula "-" in one molecule Compound (4) having 6 groups represented by "Si (OR 4 ) n-1 (R 5 ) 4-n” can be obtained in a higher yield.
  • the amount of the compound (5) used so far is an example for efficiently obtaining the target compound (4) in a good yield, and the amount of the compound (5) used is the compound ( It can be adjusted as appropriate in consideration of the overall manufacturing conditions of 4). Further, the amount of the compound (5) used so far means the total amount of all kinds of the compound (5) to be used when two or more kinds of the compound (5) are used.
  • the reaction between the compound (2) and the compound (5) may be carried out without using a solvent, but it is preferably carried out using a solvent.
  • the solvent By using the solvent, the fluidity of the reaction solution is improved, the reaction between the compound (2) and the compound (5) proceeds more smoothly, and the amount of by-products produced can be reduced.
  • the solvent is preferably one that does not have reactivity with the components used in the reaction, such as compound (2) and compound (5).
  • the solvent include ethers (compounds having an ether bond) such as tetrahydrofuran (THF), 1,4-dioxane, tetrahydropyran, dibutyl ether, 1,2-dimethoxyethane; N, N-dimethylformamide (DMF).
  • N, N-Dimethylacetamide (DMAc) and other amides Ethyl acetate, butyl acetate and other esters; 1,2-Dichloroethane, methylene chloride, chlorobenzene and other halogenated hydrocarbons (hydrocarbons having a halogen atom as a substituent) Nitriles such as propionitrile and acetonitrile (compounds having a cyano group); hydrocarbons such as toluene, n-hexane and methylcyclohexane can be mentioned.
  • DMAc N, N-Dimethylacetamide
  • Ethyl acetate, butyl acetate and other esters 1,2-Dichloroethane, methylene chloride, chlorobenzene and other halogenated hydrocarbons (hydrocarbons having a halogen atom as a substituent)
  • Nitriles such as propionitrile and acetonitrile (compounds having
  • one type of the solvent may be used alone, two or more types may be used in combination, and when two or more types are used in combination, the combination and ratio thereof may be appropriately adjusted according to the purpose. Can be adjusted.
  • the amount of the solvent used is not particularly limited, but for example, it is preferably 0 to 100 ml with respect to 1 mmol of the amount of the compound (2) used. When the amount of the solvent used is 100 ml or less, the excessive use of the solvent is suppressed.
  • one type of the other component may be used alone, two or more types may be used in combination, and when two or more types are used in combination, the combination and ratio thereof shall be determined. It can be adjusted as appropriate according to the purpose.
  • the amount of the other component used is not particularly limited and can be arbitrarily selected according to the type of the other component.
  • the reaction temperature at the time of the reaction between the compound (2) and the compound (5) may be appropriately adjusted and is not particularly limited.
  • the reaction temperature may be, for example, any of ⁇ 35 to 70 ° C. and ⁇ 35 to 40 ° C.
  • the reaction time during the reaction between the compound (2) and the compound (5) may be appropriately adjusted according to other conditions such as the reaction temperature so that the amount of the compound (4) produced is increased, and is not particularly limited. ..
  • the reaction time is, for example, preferably 1 to 168 hours, more preferably 1 to 100 hours.
  • post-treatment is carried out by a known method, and then compound (4) can be taken out by a known method.
  • post-treatment operations such as filtration, washing, extraction, pH adjustment, dehydration, and concentration are performed individually or in combination of two or more, as needed, and then concentration, crystallization, and so on.
  • Compound (4) can be extracted by reprecipitation, column chromatography, or the like. Further, the extracted compound (4) can be further subjected to operations such as crystallization, reprecipitation, column chromatography, extraction, and stirring and washing of crystals with a solvent, either alone or in combination of two or more, if necessary.
  • the desired compound (4) can be obtained. Even if a plurality of types of the compound (4) are produced, its characteristics can be inferred from the structure of the compound (4). Therefore, by selecting a post-treatment operation or a purification operation suitable for the characteristics, the target compound ( The yield of 4) can be improved. Further, the yield of the compound (4) can be improved by improving the production rate of the target compound (4) by adjusting the amount of the compound (5) used, other reaction conditions and the like. ..
  • the structure of compound (4) is, for example, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), infrared spectroscopy (IR), ultraviolet / visible spectroscopy (UV-VIS absorption spectrum), elemental analysis. It can be confirmed by a known method such as.
  • Z 40 is a hydrogen atom or a group represented by the general formula "-Si (OR 40 ) m-1 (R 50 ) 4-m". (2p 1 + 6) Z 40s may be the same or different from each other, except that one or more Z 40s are the above general formula "-Si (OR 40 ) m-1 (R 50 ) 4". It is a group represented by "-m "; m is an integer of 2 to 4; R 40 is an alkyl group, an alkenyl group or an aryl group which may have a hydrogen atom or a substituent.
  • the m-1 R 40s may be the same or different from each other, and when two or more R 40s are the alkyl group, alkenyl group or aryl group, these groups are mutual. It may be bonded to to form a ring;
  • R 50 is an alkyl group, an alkenyl group or an aryl group which may have a hydrogen atom or a substituent, and when m is 2, two of them are used.
  • R 50s may be the same or different from each other, and when two R 50s are the alkyl group, alkenyl group or aryl group, these groups may be bonded to each other to form a ring.
  • compound (40) can be used as a functional silicon material and is highly useful.
  • p 1 is to define the size of the cage of the compound (40), is 0, 1 or 2.
  • the p 1 in the general formula (40) is the same as the p 1 in the general formula (4) described above.
  • Compound (40) has a compound (40) in which p 1 is 1 and all eight Z 40s are groups represented by the formula “-Si (OCH 2 CH 3 ) 3 ”, and p 1 is 1 and 8
  • 2 CH 3 ) (CH 3 ) The compound described above (CH 3) except that it does not contain the compound represented by 2 ”and always has a group represented by the general formula“ ⁇ OR 40 ”. Same as 4).
  • the compound (40) when p 1 is 0 is represented by the following general formula (401), and the compound (40) when p 1 is 1 is represented by the following general formula (402).
  • the compound (40) when p 1 is 2 is represented by the following general formula (403).
  • Z 40 in the general formula (40) is "when p 1 is 1, all eight Z 40s are not groups represented by the formula" -Si (OCH 2 CH 3 ) 3 "", "When p 1 is 1, all eight Z 40s are not groups represented by the formula” -Si (OCH 2 CH 3 ) 2 CH 3 "” and "when p 1 is 1. In addition, all eight Z 40s are not the groups represented by the formula "-Si (OCH 2 CH 3 ) (CH 3 ) 2 ", and the groups represented by the general formula "-OR 40 " must be used. It is the same as Z 4 in the general formula (4) described above, except that it satisfies all the conditions of "having".
  • Z 40s may be the same or different from each other, except that one or two or more Z 40s are described in the general formula "-Si (OR 40)”. ) M-1 (R 50 ) 4-m ”.
  • R 40 in the general formula (40) is the same as R 4 in the general formula (4) described above.
  • R 40s are the alkyl group, alkenyl group or aryl group, these groups (alkyl group, alkenyl group or aryl group) are bonded to these groups.
  • a ring may be formed together with the oxygen atom (O) and the silicon atom (Si) to which the oxygen atom is bonded.
  • R 50 in the general formula (40) is the same as R 5 in the general formula (4) described above.
  • the two R 50 are the alkyl groups, when an alkenyl group or an aryl group, these groups (alkyl group, an alkenyl group or an aryl group) is bonded to each other, the silicon atom to which they group is attached ( A ring may be formed together with Si).
  • R 40 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms (a linear or branched alkyl group having 1 to 20 carbon atoms, and a cyclic group having 3 to 20 carbon atoms.
  • Alkyl group alkenyl group having 2 to 20 carbon atoms (linear or branched alkenyl group having 2 to 20 carbon atoms, cyclic alkenyl group having 3 to 20 carbon atoms) or aryl having 6 to 20 carbon atoms.
  • R 40 of the compound (40) When it is a group and m is 3 or more (3 or 4), m-1 (2 or) in the general formula "-Si (OR 40 ) m-1 (R 50 ) 4-m "
  • the R 40s (3) may be the same or different from each other.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 40 has a hydrogen atom, an alkyl group having 1 to 6 carbon atoms (a linear or branched alkyl group having 1 to 6 carbon atoms, and an alkyl group having 3 to 6 carbon atoms). Cyclic alkyl group), alkenyl group having 2 to 6 carbon atoms (linear or branched alkenyl group having 2 to 6 carbon atoms, cyclic alkenyl group having 3 to 6 carbon atoms) or alkenyl group having 6 to 12 carbon atoms.
  • R 40 When it is an aryl group and m is 3 or more (3 or 4), m-1 (2) in the general formula "-Si (OR 40 ) m-1 (R 50 ) 4-m " Or 3) R 40s may be the same or different from each other.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 50 is a hydrogen atom, a linear or branched alkyl group of the alkyl group (having 1 to 20 carbon atoms having 1 to 20 carbon atoms, 3 to 20 carbon atoms (Cyclic alkyl group), alkenyl group having 2 to 20 carbon atoms (linear or branched alkenyl group having 2 to 20 carbon atoms, cyclic alkenyl group having 3 to 20 carbon atoms) or 6 to 20 carbon atoms.
  • the aryl group if m is 2, the formula "-Si (OR 40) m-1 (R 50) 4-m " two R 50 in the mutually the same or different May be mentioned.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 50 is a hydrogen atom, a linear or branched alkyl group of the alkyl group (1-6 carbon atoms having 1 to 6 carbon atoms, having a carbon number of 3 to 6 cyclic alkyl group), alkenyl group having 2 to 6 carbon atoms (linear or branched alkenyl group having 2 to 6 carbon atoms, cyclic alkenyl group having 3 to 6 carbon atoms) or 6 to 6 carbon atoms a 12 aryl group, when m is 2, the formula "-Si (OR 40) m-1 (R 50) 4-m " two R 50 in the mutually the same or different There are things that may be.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 40 and R 50 are the above-mentioned preferable ones.
  • R 40 has a hydrogen atom, an alkyl group having 1 to 20 carbon atoms (a linear or branched alkyl group having 1 to 20 carbon atoms, and an alkyl group having 3 to 20 carbon atoms). Cyclic alkyl group), alkenyl group having 2 to 20 carbon atoms (linear or branched alkenyl group having 2 to 20 carbon atoms, cyclic alkenyl group having 3 to 20 carbon atoms) or alkenyl group having 6 to 20 carbon atoms.
  • R 40s may be the same or different from each other, and R 50 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms (a linear or branched alkyl group having 1 to 20 carbon atoms).
  • Cyclic alkyl group having 3 to 20 carbon atoms Cyclic alkyl group having 3 to 20 carbon atoms
  • Alkyl group having 2 to 20 carbon atoms Linear or branched alkenyl group having 2 to 20 carbon atoms, Cyclic alkenyl group having 3 to 20 carbon atoms
  • an aryl group having 6 to 20 carbon atoms when m is 2, the formula "-Si (oR 40) m-1 (R 50) 4-m " two R 50 in the , which may be the same or different from each other.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • R 40 has a hydrogen atom, an alkyl group having 1 to 6 carbon atoms (a linear or branched alkyl group having 1 to 6 carbon atoms, and an alkyl group having 3 to 6 carbon atoms). Cyclic alkyl group), alkenyl group having 2 to 6 carbon atoms (linear or branched alkenyl group having 2 to 6 carbon atoms, cyclic alkenyl group having 3 to 6 carbon atoms) or alkenyl group having 6 to 12 carbon atoms.
  • R 40s may be the same or different from each other, and R 50 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms (a linear or branched alkyl having 1 to 6 carbon atoms).
  • alkyl group having 3 to 6 carbon atoms cyclic alkyl group having 3 to 6 carbon atoms
  • alkenyl group having 2 to 6 carbon atoms linear or branched alkenyl group having 2 to 6 carbon atoms, cyclic alkenyl group having 3 to 6 carbon atoms)
  • aryl group having 6 to 12 carbon atoms when m is 2, the formula "-Si (oR 40) m-1 (R 50) 4-m " two R 50 in Can be the same or different from each other.
  • the alkyl group, alkenyl group or aryl group may have a substituent.
  • Z 41 is a hydrogen atom or a group represented by the general formula "-Si (OR 41 ) m-1 (R 51 ) 4-m ", and the six Z 41s are the same or different from each other.
  • one or more Z 41s are groups represented by the general formula "-Si (OR 41 ) m-1 (R 51 ) 4-m "; m is 2
  • R 41 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and m is 3 or more.
  • M-1 R 41s may be the same or different from each other, and when two or more R 41s are the alkyl group, alkenyl group or aryl group, these groups are bonded to each other to form a ring.
  • R 51 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms, and when m is 2, 2
  • the R 51s may be the same or different from each other, and when the two R 51s are the alkyl group, alkenyl group or aryl group, these groups may be bonded to each other to form a ring. .) Examples thereof include compounds represented by.
  • R 41 in the general formula (4011) is the general described above except that the alkyl group, the alkenyl group and the aryl group each have a limited number of carbon atoms and each has no substituent. It is the same as R 4 in the formula (4).
  • R 41s are the alkyl group, alkenyl group or aryl group, these groups (alkyl group, alkenyl group or aryl group) are bonded to these groups.
  • a ring may be formed together with the oxygen atom (O) and the silicon atom (Si) to which the oxygen atom is bonded.
  • R 51 in the general formula (4011) is the general described above, except that the alkyl group, the alkenyl group, and the aryl group each have a limited number of carbon atoms and each has no substituent. It is the same as R 5 in the formula (4).
  • R 51s are the alkyl group, alkenyl group or aryl group, these groups (alkyl group, alkenyl group or aryl group) are bonded to each other and the silicon atom to which these groups are bonded ( A ring may be formed together with Si).
  • Z 41 in the general formula (4011) is the general described above except that the alkyl group, the alkenyl group and the aryl group each have a limited number of carbon atoms and each has no substituent. It is the same as Z 4 in the formula (4).
  • Z 41 is the same as above, and eight Z 41s may be the same or different from each other, except that one or more Z 41s are the above general formula "-Si (OR). 41 ) It is a group represented by " m-1 (R 51 ) 4-m”.) Compounds represented by (however, all eight Z 41s have the formula "-Si (OCH 2 CH 3 ) 3 ", the formula “-Si (OCH 2 CH 3 ) 2 CH 3 ", or the formula "-Si (OCH 2 CH 3)". 2 CH 3 ) (excluding the compound which is the group represented by CH 3 ) 2 ”).
  • Z 41 is the same as above, and 10 Z 41 may be the same or different from each other, except that one or two or more Z 41 are the above general formula "-Si (OR). 41 ) It is a group represented by " m-1 (R 51 ) 4-m".) Examples thereof include compounds represented by.
  • Examples of the preferred compound (40) include the same as the preferred compound (4) listed above.
  • Compound (40) can be produced by the method for producing a compound according to an embodiment of the present invention, which has been described above. However, as the compound (5), a compound in which n is an integer of 2 to 4 is used.
  • Compound (4021) -1 (composition formula: Si 16 O 36 C 32 H 88 , "Si 8 O 12 [OSI (OEt) 2 H] 8 ") is produced from various NMR spectra of this colorless and transparent solution. It was confirmed. By concentrating this colorless transparent solution until its volume was reduced to about half (weight 1 g), an excess amount of the raw material was removed to obtain a DMF solution of compound (4021) -1 containing DMAc (yield 69%). ). The NMR data of the obtained compound (4021) -1 is shown below.
  • Example 2 Compound (22) -5, which is a mixed crystal containing DMAc, was used as compound (2), and compound (4021) -2 was produced as compound (4). More specifically, it is as follows. Compound (22) -5 (0.01 mmol, 16.6 mg) was dissolved in DMF (0.3 ml) at room temperature. Tetramethoxysilane (152 mg, 1.00 mmol) was added dropwise to the DMF solution of compound (22) -5 obtained above at room temperature, and then the mixture was stirred as it was at room temperature.
  • FIG. 1 shows NMR data at the stage of stirring time of 6 hours, 1 day, 2 days, 3 days and 4 days.
  • Example 3 Compound (22) -4, which is a mixed crystal containing DMAc, was used as compound (2), and compound (4021) -3 was produced as compound (4). More specifically, it is as follows. Compound (22) -4 (0.025 mmol, 37.6 mg) was dissolved in DMF (1 ml) and the resulting solution was cooled at ⁇ 30 ° C. for 90 minutes. A solution in which diethoxymethylsilane (269 mg, 2.00 mmol) was dissolved in DMF (1 ml) was prepared, and the DMF solution of this diethoxymethylsilane was used as the cooling compound (22) -1 obtained above. A colorless transparent solution was obtained by adding dropwise to the DMF solution at room temperature and then stirring for 2 hours.
  • Example 4 Compound (22) -6, which is a mixed crystal containing DMAc, was used as compound (2), and compound (4021) -4 was produced as compound (4). More specifically, it is as follows. Compound (22) -6 (1.00 mmol, 1.73 g) was dissolved in DMF (10 ml) at room temperature. Vinyl trimethoxysilane (4.86 g, 32.8 mmol) was added dropwise to the DMF solution of compound (22) -6 obtained above at room temperature, and the mixture was stirred at 60 ° C. for 6 hours to be colorless and transparent. A solution was obtained.
  • the present invention can be used as a functional silicon material or an intermediate thereof, and further as a method for producing these.

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Abstract

L'invention concerne un procédé de production d'un composé, selon lequel un composé représenté par la formule générale (2) (dans laquelle p1 vaut 0, 1 ou 2) est mis à réagir avec un composé représenté par la formule générale (5) (dans laquelle n est un nombre entier de 1 à 4 ; R4 représente soit un atome d'hydrogène, soit un groupe alkyle, un groupe alcényle, soit un groupe aryle qui peuvent chacun avoir un substituant, à condition qu'au moins un R4 représente un groupe alkyle, un groupe alcényle ou un groupe aryle ; et R5 représente soit un atome d'hydrogène, soit un groupe alkyle, un groupe alcényle, soit un groupe aryle qui peuvent chacun avoir un substituant) de manière à obtenir un composé représenté par la formule générale (4) (dans laquelle : Z4 représente un atome d'hydrogène ou un groupe représenté par la formule générale "-Si(OR4)n-1(R5)4-n", à condition qu'un ou plusieurs de Z4 soit un groupe représenté par la formule générale "-Si(OR4)n-1(R5)4-n" ; et n, p1, R4 et R5 sont tels que définis ci-dessus).
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