Classifications

• • 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

Definitions

• 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. 2019-199348 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.
• Non-Patent Document 1 it is necessary to use a large excess amount of chlorodimethylsilane ((CH 3 ) 2 HSiCl) with respect to the raw material compound (90) in order to obtain the compound (91). There was a problem that there was. This is because compound (90), which is a silicate compound, contains a large amount of hydrated water.
• 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):
• R 1 , R 2 and R 3 are alkyl groups or aryl groups which may independently have a hydrogen atom or a substituent, respectively, and are among R 1 , R 2 and R 3. When two or more are the alkyl or aryl groups, these groups may be bonded to each other to form a ring; X is a halogen atom.
• Z 1 is a group represented by hydrogen atom or formula "-SiR 1 R 2 R 3" may be the same or different from each other (2p 1 +6) number of Z 1, provided that , one or more Z 1, the general formula is a group represented by "-SiR 1 R 2 R 3"; p 1, R 1, R 2 and R 3 are the same as above .)
• a method for producing a compound for obtaining the compound represented by is provided.
• Z 10 is a hydrogen atom or a group represented by the general formula "-SiR 10 R 20 R 30 ", and (2p 1 + 6) Z 10s. May be the same or different from each other, except that one or more Z 10s are groups represented by the general formula "-SiR 10 R 20 R 30 "; R 10 , R 20 and R.
• Reference numeral 30 denotes an alkyl group or an aryl group which may independently have a hydrogen atom or a substituent, and two or more of R 10 , R 20 and R 30 are the alkyl group or the aryl group.
• the R 10 , R 20 and R 30 are independently hydrogen atoms, alkyl groups having 1 to 20 carbon atoms or aryls having 6 to 20 carbon atoms. It may be a group.
• the R 10 , R 20 and R 30 are independently hydrogen atoms, alkyl groups having 1 to 6 carbon atoms or aryls having 6 to 12 carbon atoms, respectively. It may be a group.
• the present invention has the following general formula (1021):
• Z 11 is a hydrogen atom or a group represented by the general formula "-SiR 11 R 21 R 31 ", and eight Z 11s may be the same or different from each other, but one or one.
• R 11 , R 21 and R 31 are the alkyl groups or aryl groups of the above alkyl groups or aryl groups having 6 to 12 carbon atoms, these groups are bonded to each other to form a ring.
• the Z 11 is a group represented by the formula "-Si (CH 3) 3", and one of Z 11 is a hydrogen atom compound, 6 Z 11 is the formula "-Si (CH 3) 3 a group represented by "and two Z 11 compound is a hydrogen atom, a group five Z 11 represented by the formula" -Si (CH 3) 3 ', 3 Z 11 is a hydrogen atom, except for compounds).
• a novel cage-type siloxane compound and a method for producing the same are provided.
• R 1 , R 2 and R 3 are alkyl groups or aryl groups which may independently have a hydrogen atom or a substituent, respectively, and are among R 1 , R 2 and R 3. When two or more are the alkyl or aryl groups, these groups may be bonded to each other to form a ring; X is a halogen atom.
• Z 1 is a group represented by hydrogen atom or formula "-SiR 1 R 2 R 3" may be the same or different from each other (2p 1 +6) number of Z 1, provided that , one or more Z 1, the general formula is a group represented by "-SiR 1 R 2 R 3"; p 1, R 1, R 2 and R 3 are the same as above .
• This is a method for producing a compound (1), which obtains a compound represented by (in the present specification, may be referred to as "compound (1)").
• a cage-type siloxane compound can be produced by a practical method without using a large excess amount of the raw material compound.
• the target compound (1) will be described.
• Compound (1) is represented by the general formula (1).
• p 1 is to define the size of the cage of the compound (1) is 0, 1 or 2. That is, the compound (1) when p 1 is 0 is represented by the following general formula (11) (in the present specification, this compound may be referred to as “compound (11)”), and p 1
• the compound (1) when is 1 is represented by the following general formula (12) (in the present specification, this compound may be referred to as “compound (12)”), and p 1 is 2.
• the compound (1) in the case is represented by the following general formula (13) (in the present specification, this compound may be referred to as "compound (13)").
• Z 1 is a hydrogen atom (-H) or a group represented by the general formula "-SiR 1 R 2 R 3".
• R 1 , R 2 and R 3 are each independently an alkyl group or an aryl group which may have a hydrogen atom or a substituent.
• the alkyl group in R 1 , R 2 and R 3 may be linear, branched or cyclic.
• the number of carbon atoms of the linear or branched alkyl group in R 1 , R 2 and R 3 is not particularly limited, but 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 cyclic alkyl group in R 1 , R 2 and R 3 may be 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 in R 1 , R 2 and R 3 may be a mixture of a linear or branched chain structure and a cyclic structure.
• 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 aryl group in R 1 , R 2 and R 3 may be monocyclic or 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 is substituted with the alkyl group in R 1 ⁇ R 3 A group having a similar structure 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 and aryl group in R 1 , R 2 and R 3 may have a substituent.
• the fact that an alkyl group and an aryl group have a substituent is one or one of these groups. It means that two or more hydrogen atoms are 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.
• Examples of the substituent in R 1 , R 2 and R 3 include halogen atoms such as chlorine atom, bromine atom and iodine atom; hydroxyl group; carboxy group; one methylene group (-CH 2- ), or two.
• Substituted alkyl groups, aryl groups and the like can be mentioned.
• alkyl group in "a methylene group, an oxygen atom, a carbonyl group, or an alkyl group substituted oxycarbonyl group" for example, the same ones as the alkyl group in R 1, R 2 and R 3 Can be mentioned.
• alkyl group in which the methylene group is substituted with an oxygen atom, a carbonyloxy group, or an oxycarbonyl group the position of substitution of the methylene group by the substituent (oxygen atom, carbonyloxy group, or oxycarbonyl group) is
• the number of substituents is not particularly limited and 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 1 , R 2 and R 3 are independently hydrogen atoms, alkyl groups having 1 to 20 carbon atoms (linear or branched alkyl groups having 1 to 20 carbon atoms, cyclic groups having 3 to 20 carbon atoms, respectively). Alkyl group) or an aryl group having 6 to 20 carbon atoms, each independently having a hydrogen atom and an alkyl group having 1 to 6 carbon atoms (a linear or branched alkyl having 1 to 6 carbon atoms). A group, a cyclic alkyl group having 3 to 6 carbon atoms) or an aryl group having 6 to 12 carbon atoms is more preferable. In such R 1 , R 2 and R 3 , the alkyl group or aryl group may have a substituent.
• the ring formed by bonding two or more of R 1 , R 2 and R 3 to each other is a silicon-containing aliphatic ring or silicon-containing ring containing a silicon atom as an atom forming a ring skeleton. It is an aromatic ring.
• the bonding position of R 1 , R 2 or R 3 when forming the ring 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 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 1 , R 2 or R 3 when forming the ring may be 1 or 2 or more. That is, the ring may be either monocyclic or polycyclic.
• Z 1 may be the same or different from each other. That, (2p 1 +6) number of Z 1 may all be the same, may be different, all may be the same part only.
• Z 1 is a hydrogen atom
• one or more Z 1 is a group represented by the general formula "-SiR 1 R 2 R 3"
• the may be a group represented by (2p 1 +6) number of Z 1 are all the general formula "-SiR 1 R 2 R 3".
• a trialkylsilyl group for example, a trialkylsilyl group, a dialkylsilyl group, a monoalkylsilyl group, a triarylsilyl group, a diarylsilyl group, a mono Examples thereof include an arylsilyl group, a dialkyl monoarylsilyl group, a monoalkyldiarylsilyl group, a monoalkyl monoarylsilyl group, and a silyl group (-SiH 3 ).
• Compound (2) is represented by the general formula (2).
• P 1 in the general formula (2) is the same as p 1 in the general formula (1).
• 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.
• a compound (2) for example, a crystal
• 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 (3) is represented by the general formula (3).
• the monovalent group having the structure in which X in the compound (3) is removed is the same as the group represented by the general formula “ ⁇ SiR 1 R 2 R 3 ” in Z 1 in the compound (1). ..
• R 1 in the general formula (3), R 2 and R 3 are the same as R 1, R 2 and R 3 in the general formula (1).
• X is a halogen atom.
• the halogen atom include a chlorine atom, a bromine atom, an iodine atom and the like.
• the compound (3) when X is a chlorine atom more specifically, for example, trialkylsilyl chloride, dialkylsilyl chloride, monoalkylsilyl chloride, triarylsilyl chloride, diarylsilyl chloride, monoarylsilyl.
• examples thereof include chloride, dialkyl monoarylsilyl chloride, monoalkyldiarylsilyl chloride, monoalkyl monoarylsilyl chloride and the like.
• Compound (1) is obtained by reacting compound (2) with compound (3).
• the compound (3) 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 (1). When two or more compounds (3) are used, their combinations and ratios can be appropriately adjusted according to the intended purpose.
• the amount of compound (3) used can be appropriately adjusted according to the structure of the target compound (1) and the like.
• the amount of compound (3) used can be adjusted according to the number of groups represented by the general formula "-SiR 1 R 2 R 3" in the target compound (1).
• the amount of the compound (3) is, when the relative amount of the compound (2) is 1 to 2 times molar quantity, the formula in one molecule " A compound (1) having 1 to 2 groups represented by " -SiR 1 R 2 R 3" is preferably obtained.
• the amount of the compound (3) is, relative to the amount of the compound (2), when it is 3 to 4 times the molar amount of the general formula in a molecule " A compound (1) having 3 to 4 groups represented by " -SiR 1 R 2 R 3" is preferably obtained.
• the amount of the compound (3) is, relative to the amount of the compound (2), when it is 5-6 times the molar amount of the general formula in a molecule "
• a compound (1) having 5 to 6 groups represented by " -SiR 1 R 2 R 3" is preferably obtained.
• the general formula "-" in one molecule The compound (1) having 6 groups represented by " SiR 1 R 2 R 3" can be obtained in a higher yield. In this case, for example, when the amount of the compound (3) used is 10 times the molar amount or less, the excessive use of the compound (3) is suppressed.
• the general amount in one molecule when p 1 is 1 or 2, and the amount of compound (3) used is 7 to 8 times the molar amount of compound (2) used, the general amount in one molecule.
• a compound (1) having 7 to 8 groups represented by the formula “ ⁇ SiR 1 R 2 R 3” is preferably obtained.
• the general formula "-" in one molecule when p 1 is 1, and the amount of compound (3) used is 8 times the molar amount or more of the amount of compound (2) used, the general formula "-" in one molecule.
• the compound (1) having 8 groups represented by " SiR 1 R 2 R 3" can be obtained in a higher yield.
• the amount of the compound (3) used is preferably 17 times the molar amount or less, more preferably 12 times the molar amount or less, the overuse of the compound (3) is suppressed.
• the amount of compound (3) used is 9 to 10 times the molar amount of compound (2) used
• the above general formula "in one molecule" A compound (1) having 9 to 10 groups represented by " -SiR 1 R 2 R 3" is preferably obtained.
• the amount of compound (3) used is 10 times the molar amount or more of the amount of compound (2) used, the general formula "-" in one molecule.
• the compound (1) having 10 groups represented by " SiR 1 R 2 R 3" can be obtained in a higher yield. In this case, for example, when the amount of the compound (3) used is 14 times the molar amount or less, the excessive use of the compound (3) is suppressed.
• the amount of the compound (3) used so far is an example for efficiently obtaining the target compound (1) in a good yield, and the amount of the compound (3) used is the compound (3). It can be adjusted as appropriate in consideration of the overall manufacturing conditions of 1). In addition, the amount of the compound (3) used so far means the total amount of all kinds of the compound (3) used when two or more kinds of the compound (3) are used.
• the base is preferably an organic base.
• organic base include aromatic amines such as aniline, pyridine and piperidine; and aliphatic amines such as triethylamine and diisopropylethylamine.
• one type of base 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 base used can be adjusted, for example, according to the amount of the compound (3) used.
• the amount of the base used is preferably 1 to 2 times the molar amount of the compound (3), and may be, for example, 1 to 1.5 times the molar amount.
• the amount of the base used is 1 times the molar amount or more, the amount of the compound (1) produced is further increased.
• the amount of the base used is twice the molar amount or less, the excessive use of the base is suppressed.
• the reaction between the compound (2) and the compound (3) 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 (3) 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 (3).
• 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, more preferably 10 to 50 ml, with respect to 1 mmol of the compound (2) used.
• the amount of the solvent used is 10 ml or more, the effect of using the solvent can be obtained more remarkably.
• 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 (3) may be appropriately adjusted and is not particularly limited.
• the reaction temperature is preferably 10 to 40 ° C, and may be room temperature such as 18 to 30 ° C.
• the reaction time during the reaction between the compound (2) and the compound (3) may be appropriately adjusted according to other conditions such as the reaction temperature so that the amount of the compound (1) produced is increased, and is not particularly limited. ..
• the reaction time is, for example, preferably 1 to 72 hours, more preferably 1 to 60 hours.
• compound (1) 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 (1) can be extracted by reprecipitation, column chromatography, or the like. Further, the extracted compound (1) 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. It may be purified by performing it once or twice or more.
• post-treatment is carried out by a known method as necessary, and then the compound (1) is not taken out. Other steps may be performed.
• the desired compound (1) can be obtained. Even if a plurality of types of the compound (1) are produced, its characteristics can be inferred from the structure of the compound (1). Therefore, by selecting a post-treatment operation or a purification operation suitable for the characteristics, the target compound ( The yield of 1) can be improved. Further, the yield of the compound (1) can be improved by improving the production rate of the target compound (1) by adjusting the amount of the compound (3) used, other reaction conditions and the like. ..
• the structure of compound (1) 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.
• NMR nuclear magnetic resonance
• MS mass spectrometry
• IR infrared spectroscopy
• UV-VIS absorption spectrum ultraviolet / visible spectroscopy
• Z 10 is a hydrogen atom or a group represented by the general formula "-SiR 10 R 20 R 30 ", and (2p 1 + 6) Z 10s. May be the same or different from each other, except that one or more Z 10s are groups represented by the general formula "-SiR 10 R 20 R 30 "; R 10 , R 20 and R.
• Reference numeral 30 denotes an alkyl group or an aryl group which may independently have a hydrogen atom or a substituent, and two or more of R 10 , R 20 and R 30 are the alkyl group or the aryl group.
• these groups may be bonded to each other to form a ring.
• p 1 is 1, and all eight Z 10s are represented by the formula "-Si (CH 3 ) 3 ", the formula “-Si (CH 3 ) 2 H”, and the formula "-Si ((((CH 3) 3) 3".
• compound (10) 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 (10), is 0, 1 or 2.
• the p 1 in the general formula (10) is the same as the p 1 in the general formula (1) described above.
• Compound (10) has a compound (10) in which p 1 is 1 and all eight Z 10s are groups represented by the formula “-Si (CH 3 ) 3 ”, and compound (10) has p 1 in 1 and eight.
• Z 10 in the general formula (10) is "when p 1 is 1, all eight Z 10s are not groups represented by the formula" -Si (CH 3 ) 3 "", "p. When 1 is 1, all 8 Z 10s are not groups represented by the formula "-Si (CH 3 ) 2 H”"," 8 Z when p 1 is 1.
• All 10 are not groups represented by the formula "-Si ((4-CH 3 ) C 6 H 4 ) (CH 3 ) 2 " (dimethyl (4-methylphenyl) silyl group) "," p 1 is When 1, all eight Z 10s are groups represented by the formula “-Si ((4-CBr 3 ) C 6 H 4 ) (CH 3 ) 2 " (4-tribromomethylphenyl (dimethyl)). It does not become a silyl group) ",” When p 1 is 1, all eight Z 10s are represented by the formula "-Si ((4-COOH) C 6 H 4 ) (CH 3 ) 2 ".
• all eight Z 10s are not groups represented by the formula "-Si (CH 3 ) 2 CH 2 Cl”"
• p 1 When p 1 is 1, eight Z 10s are All are not groups represented by the formula "-Si (CH 3 ) 2 (OSi (CH 3 ) 3 )""
• p 1 When p 1 is 1, seven Z 10s are the formula" -Si ( CH 3 ) It is a group represented by " 3 ", and one Z 10 is not a hydrogen atom.
• Z 10s are of the formula "-Si.” (CH 3 ) 3 "is a group represented by” and two Z 10s are not hydrogen atoms ", and" when p 1 is 1, five Z 10s are of the formula " -Si (CH 3 ) 3 "is a group represented by”, and three Z 10s are not hydrogen atoms ", except that the general formula described above is satisfied. It is the same as Z 1 in (1).
• Z 10s may be the same or different from each other, except that one or two or more Z 10s are described in the general formula “ ⁇ SiR 10 R 20”. It is a group represented by "R 30".
• R 10 , R 20 and R 30 in the general formula (10) are the same as R 1 , R 2 and R 3 in the general formula (1) described above, respectively.
• R 10 , R 20 and R 30 are the above-mentioned alkyl group or aryl group, these groups (alkyl group or aryl group) are bonded to these groups.
• a ring may be formed together with the silicon atom (Si).
• R 10 , R 20 and R 30 are independently hydrogen atoms and alkyl groups having 1 to 20 carbon atoms (linear or branched chains having 1 to 20 carbon atoms). Alkyl groups (cyclic alkyl groups having 3 to 20 carbon atoms) or aryl groups having 6 to 20 carbon atoms can be mentioned. In R 10 , R 20 and R 30 of such compound (10), the alkyl group or aryl group may have a substituent.
• R 10 , R 20 and R 30 are independently hydrogen atoms and alkyl groups having 1 to 6 carbon atoms (linear or branched chains having 1 to 6 carbon atoms, respectively). , A cyclic alkyl group having 3 to 6 carbon atoms) or an aryl group having 6 to 12 carbon atoms.
• the alkyl group or aryl group may have a substituent.
• Z 11 is a hydrogen atom or a group represented by the general formula "-SiR 11 R 21 R 31 ", and the six Z 11s may be the same or different from each other, but one or one.
• the two or more Z 11, formula "-SiR 11 R 21 R 31" in be a group represented by; R 11, R 21 and R 31 are independently a hydrogen atom, 6
• R 11 , R 21 and R 31 are the alkyl groups or aryl groups of the above alkyl groups or aryl groups having 6 to 12 carbon atoms, these groups are bonded to each other to form a ring. It may be formed.
• Examples thereof include compounds represented by.
• R 11 , R 21 and R 31 in the general formula (1011) are first described except that the alkyl group and the aryl group each have a limited number of carbon atoms and do not have a substituent. It is the same as R 1 , R 2 and R 3 in the general formula (1) described.
• R 11 , R 21 and R 31 are the above-mentioned alkyl group or aryl group, these groups (alkyl group or aryl group) are bonded to these groups.
• a ring may be formed together with the silicon atom (Si).
• Z 11 in the general formula (1011) has the above-described general formula (1) except that the alkyl group and the aryl group each have a limited number of carbon atoms and each has no substituent. ) Is the same as Z 1 in.
• Z 11 are the same as described above, may be the same or different from each other 8 Z 11, provided that one or more of Z 11, the formula "-SiR 11 R It is a group represented by " 21 R 31".
• the Z 11 is a group represented by the formula "-Si (CH 3) 3", and one of Z 11 is a hydrogen atom compound, 6 Z 11 is the formula "-Si (CH 3) 3 a group represented by "and two Z 11 compound is a hydrogen atom, a group five Z 11 represented by the formula" -Si (CH 3) 3 ', 3 Z ( Excluding compounds in which 11 is a hydrogen atom).
• Z 11 is the same as above, 10 Z 11 may be the same or different, provided that one or more of Z 11, the formula "-SiR 11 R It is a group represented by " 21 R 31".) Examples thereof include compounds represented by.
• Examples of the preferred compound (10) are the same as those of the preferred compound (1) listed above (however, in the general formula (10), p 1 is 1 and all eight Z 10s are of the formula "-”.
• p 1 is 1, five Z 10s are groups represented by the formula "-Si (CH 3 ) 3 ", and three Z 10s are hydrogen atoms. (Except for compounds that are used).
• Compound (10) can be produced by the method for producing a compound according to an embodiment of the present invention, which has been described above.
• Example 1 Compound (22) -1, which is a mixed crystal containing DMAc, was used as compound (2), and compound (1021) -1 was produced as compound (1). More specifically, it is as follows. Compound (22) -1 (311 mg, 0.20 mmol) was dissolved in THF (6 ml), and aniline (176 mg, 2.4 mmol) and phenyldihydrochlorosilane (285 mg, 2.0 mmol) were added to the obtained solution. , Stirred at room temperature for 2 hours to obtain a suspended solution.
• Example 2 Compound (22) -2, which is a mixed crystal containing DMAc, was used as compound (2), and compound (1021) -2 was produced as compound (1). More specifically, it is as follows. Compound (22) -2 (106 mg, 0.10 mmol) was dissolved in THF (3 ml), and aniline (78.5 mg, 0.84 mmol) and chlorodimethylsilane (79.6 mg, 0.84 mmol) were added to the obtained solution. ) was added, and the mixture was stirred at room temperature for 90 minutes to obtain a suspended solution. From various NMR spectra of this suspension solution, it was confirmed that compound (1021) -2 ("Si 8 O 12 [OSiMe 2 H] 8 ”) was produced.
• Example 3 Compound (22) -3, which is a mixed crystal containing DMAc, was used as compound (2), and compound (1021) -3 and compound (1021) -4 were produced as compound (1). More specifically, it is as follows. Aniline (140 mg, 1.5 mmol) and THF (2 ml) were mixed to prepare an aniline solution having a concentration of 0.70 mmol / ml. Separately, chlorotrimethylsilane (163 mg, 1.5 mmol) and THF (2 ml) were mixed to prepare a chlorotrimethylsilane solution having a concentration of 0.68 mmol / ml.
• reaction solution was further added with the above-mentioned aniline solution (14 ⁇ l, 0.9 mg as aniline, 0.01 mmol) and the above-mentioned chlorotrimethylsilane solution (16 ⁇ l, chlorotrimethylsilane).
• aniline solution 14 ⁇ l, 0.9 mg as aniline, 0.01 mmol
• chlorotrimethylsilane solution 16 ⁇ l, chlorotrimethylsilane.
• a mixture of compound (1021) -3 and compound (1021) -4 was obtained by adding 1.1 mg (0.01 mmol) and reacting at room temperature for another 23 hours.
• the NMR data of the obtained compounds (1021) -3 and compound (1021) -4 are shown below.
• Example 4 Compound (22) -3, which is a mixed crystal containing DMAc, was used as compound (2), and compound (1021) -5 was produced as compound (1). More specifically, it is as follows. Compound (22) -3 (1.55 g, 1.00 mmol) was dissolved in THF (30 ml), and aniline (724 mg, 9.90 mmol) and n-butylchlorodimethylsilane (1.49 g, 9.90 mmol) was added and the mixture was stirred at room temperature for 3 hours to obtain a suspended solution.
• 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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