WO2021085535A1 - Compound and production method therefor - Google Patents

Abstract

A method for producing a compound represented by general formula (1) by reacting a compound represented by general formula (2) (wherein p₁ is 0, 1, or 2) with a compound represented by general formula (3) (wherein R¹, R², and R³ are each independently a hydrogen atom, an alkyl group, or an aryl group and in the case where two or all of the R¹, R², and R³ are each the alkyl or aryl group, these groups may be bonded to each other to form a ring; and X is a halogen atom). (In general formula (1), Z¹ is a hydrogen atom or a group represented by the general formula -SiR¹R²R³, and the (2p₁+6) Z¹ moieties may be the same or different but one or more of the Z¹ moieties are each the group of the general formula -SiR¹R²R³; and p₁, R¹, R², and R³ are the same as defined above.)

Description

Compounds and methods for producing them

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.

For example, as one of such cage-type siloxane compounds, a compound represented by the following formula (90) by the synthetic route shown below (in this specification, it may be referred to as "compound (90)"). It is disclosed that a compound represented by the following formula (91) (in this specification, it may be referred to as “compound (91)”) was obtained using the above as a raw material (see Non-Patent Document 1).

However, in the method described in 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.

As described above, some conventional cage-type siloxane compounds cannot be produced by a practical method, and improvement of the production method has been desired.
Further, at present, it cannot be said that the search for a cage-type siloxane compound has been sufficiently performed, and the search for a new cage-type siloxane compound has also 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):

(In the formula, p ₁ is 0, 1 or 2.)
The compound represented by and the following general formula (3):

(In the formula, 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.)
By reacting with the compound represented by, the following general formula (1):

(Wherein, ^{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 .)
Provided is a method for producing a compound for obtaining the compound represented by.

Further, the present invention has the following general formula (10):

(In the formula, p ₁ is 0, 1 or 2; 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. In some cases, these groups may be bonded to each other to form a ring.)
Compounds represented by (where p ₁ is 1 and ^{all eight Z 10s} are of the formula "-Si (CH ₃ ) ₃ ", of the formula "-Si (CH ₃ ) ₂ H", of the formula "-Si ( (4-CH ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ", formula" -Si ((4-CBr ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ", formula" -Si ((4-COOH) ) C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ ) ”, formula“ -Si (CH ₃ ) ₂ (CH = CH ₂ ) ”, formula A group represented by "-Si (CH = CH ₂ ) ₃ ", the formula "-Si (CH ₃ ) ₂ CH ₂ Cl", or the formula "-Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ )". A compound in which p ₁ is 1, seven Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ", and one Z ¹⁰ is a hydrogen atom, and p. ₁ is 1, 6 Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ^{", 2 Z 10s} are hydrogen atoms, and p ₁ is 1. (Excluding compounds in which 5 Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ^{" and 3 Z 10s} are hydrogen atoms).

In the compound represented by the general formula (10) of the present invention, 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.
In the compound represented by the general formula (10) of the present invention, 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.
Further, the present invention has the following general formula (1021):

(In the formula, 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. 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 ^{When two or more of 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.)
Compound represented by (where eight ^{Z 11} are all expressions "-Si _{(CH 3) 3",} the formula "-Si _{(CH 3) 2} H", the formula _{"-Si ((4-CH 3)} C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si ((4-CBr ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si ((4-COOH) C ₆ H ₄ ) ( CH ₃ ) ₂ ”, formula“ -Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ ) ”, formula“ -Si (CH ₃ ) ₂ (CH = CH ₂ ) ”, formula“ -Si (CH = CH) ₂ ) ₃ ", the compound which is the group represented by the formula" -Si (CH ₃ ) ₂ CH ₂ Cl ", or the formula" -Si (CH ₃ ) ₂ (OSi (CH ₃ ) _{3) ", and 7 pieces.} 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).

According to the present invention, a novel cage-type siloxane compound and a method for producing the same are provided.

<< Compound manufacturing method >>
A method for producing a compound according to an embodiment of the present invention is described in the following general formula (2):

(In the formula, p ₁ is 0, 1 or 2.)
(In the present specification, it may be referred to as "Compound (2)") and the following general formula (3):

(In the formula, 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.)
By reacting with a compound represented by (in the present specification, it may be referred to as "compound (3)"), the following general formula (1):

(Wherein, ^{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)").

According to the production method of the present embodiment, unlike the conventional method for producing the compound (91), a cage-type siloxane compound can be produced by a practical method without using a large excess amount of the raw material compound.
Hereinafter, first, the target compound (1) will be described.

<Compound (1)>
Compound (1) is represented by the general formula (1).
In 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)").

(In the formula, Z ¹ is the same as above.)

That is, the method for producing the compound (1) (compound (11)) when _{p 1 is 0 is described in the following formula (21):}

The compound represented by and the following general formula (3):

(In the formula, R ¹ , R ² , R ³ and X are the same as above.)
By reacting with the compound represented by (compound (3)), the following general formula (11):

(In the formula, Z ¹ is the same as above.)
This is a method for producing the compound (11), which obtains the compound represented by (compound (11)).

The method for producing the compound (1) (compound (12)) when _{p 1 is 1 is described in the following formula (22):}

Compounds represented by (2,4,6,8,10,12,14,16,17,18,19,20-dodecaoxa 1,3,5,7,9,11,13,15-octacilapenta cyclo ^{[9.5.1.1 3,9 .1 5,15 .1 7,13.} ] icosane 1,3,5,7,9,11,13,15- octanol (CAS No. 119558-12-2 ), In the present specification, it may be referred to as “compound (22)”) and the following general formula (3):

(In the formula, R ¹ , R ² , R ³ and X are the same as above.)
By reacting with the compound represented by (compound (3)), the following general formula (12):

(In the formula, Z ¹ is the same as above.)
This is a method for producing the compound (12), which obtains the compound represented by (compound (12)).

Further, the method for producing the compound (1) (compound (13)) when _{p 1 is 2 is described in the following formula (23):}

The compound represented by and the following general formula (3):

(In the formula, R ¹ , R ² , R ³ and X are the same as above.)
By reacting with the compound represented by (compound (3)), the following general formula (13):

(In the formula, Z ¹ is the same as above.)
This is a method for producing the compound (13), which obtains the compound represented by (compound (13)).

In the general formula (1), Z ¹ is a hydrogen atom (-H) or a group represented by the ^{general formula "-SiR 1} R ² R ^3". And 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, hexadecyl group , Heptadecyl group, octadecyl group, nonadecil group, icosyl group and the like.
The linear or branched alkyl group preferably has 1 to 10 carbon atoms, and may be, for example, any of 1 to 6 and 1 to 3.

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-. Examples thereof include an adamantyl group and a tricyclodecyl group.
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. A group having a structure in which one or more hydrogen atoms in the alkyl group in the form are substituted with the above-mentioned cyclic alkyl group; methylcyclopentyl group, ethylcyclopentyl group, methylcyclohexyl group, ethylcyclohexyl group, dimethylcyclohexyl 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.}
In the present specification, ^{not only in the case of R 1} , R ² and R ³ , but unless otherwise specified, 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. In the present specification, 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. The above non-adjacent methylene groups are oxygen atoms (-O-), carbonyloxy groups (-C (= O) -O-), or oxycarbonyl groups (-OC (= O)-). Substituted alkyl groups, aryl groups and the like can be mentioned.

Above The 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.

In the above-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.

In the group represented by the general formula "-SiR ¹ R ² R ³ ", when two or more (two or three) of ^{R 1} , R ² and R ^{3 are the alkyl group or the aryl group.} These groups (alkyl groups or aryl groups) may be bonded to each other to form a ring together with the silicon atom (Si) to which these groups are bonded.

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. For example, when R ¹ , R ² or R ³ has a chain structure, the bond position may be a carbon atom at the end of the chain structure or a non-terminal carbon atom. Good. However, when 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.

In the general formula (1), (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 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.

However, in the general formula (1) is not that all of ^{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" , and 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".

Table In the general formula (1), if one or more ^{Z 1} is a hydrogen atom (i.e., Compound (1), all of ^{Z 1} is the general formula "-SiR ¹ R ² R ^3" The bonding position of the group represented by the general formula "-SiR ¹ R ² R ^{3" is not particularly limited.}

More specifically, as the group represented by the general formula "-SiR ¹ R ² R ³ ", 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 ).

Examples of the preferred compound (1) are listed below. However, compound (1) is not limited to these.

As another example of the preferred compound (1), in the alkyl group or aryl group in the compound (1) listed so far, one or two or more hydrogen atoms are substituted with the substituent described above. Some are also listed.

Next, the raw materials, compound (2) and compound (3), will be described in order.

<Compound (2)>
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.

As the compound (2), 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. By using such a compound (2) (for example, a crystal) that does not contain hydrated water, it is possible to avoid using a large excess amount of the raw material for producing the compound (1) such as the compound (3), and the compound (for example). 1) can be produced efficiently and in a good yield.

Compound (2) may not contain a molecule of a solvent component, or may contain a molecule of a solvent component other than water. Examples of the solvent component include N, N-dimethylacetamide (DMAc) and the like. 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).
For example, in the compound (2) containing a molecule of DMAc, 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)>
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).

In the general formula (3), X is a halogen atom.
Examples of the halogen atom include a chlorine atom, a bromine atom, an iodine atom and the like.

For example, as 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.
Next, a general method for reacting the compound (2) with the compound (3) will be described.

<Reaction conditions between compound (2) and compound (3)>
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.

In this specification, the description of the number of types of compounds (1), (2) and (3) does not consider the stereoisomers unless otherwise specified.

The amount of compound (3) used can be appropriately adjusted according to the structure of the target compound (1) and the like.
For example, 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).}

For example, regardless of the value of p _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.}
For example, regardless of the value of p _1, 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.}
For example, regardless of the value of p _1, 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.}
For example, when p ₁ is 0 and the amount of compound (3) used is 6 times the molar amount or more of the amount of compound (2) used, 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.
For example, 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.}
For example, 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.} In this case, for example, when 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.
For example, when p ₁ is 2, and 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.}
For example, when p ₁ is 2, and 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.

[base]
When the compound (2) and the compound (3) are reacted, it is preferable to use a base. By using a base, the amount of compound (1) produced is significantly increased.

The base is preferably an organic base.
Examples of the organic base include aromatic amines such as aniline, pyridine and piperidine; and aliphatic amines such as triethylamine and diisopropylethylamine.

When the above bases are used, 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.

When the base is used, the amount of the base used can be adjusted, for example, according to the amount of the compound (3) used.
In that case, 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. When the amount of the base used is 1 times the molar amount or more, the amount of the compound (1) produced is further increased. When the amount of the base used is twice the molar amount or less, the excessive use of the base is suppressed.

[solvent]
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. 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).
Examples of 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.

When a solvent is used, 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. When the amount of the solvent used is 10 ml or more, the effect of using the solvent can be obtained more remarkably. When the amount of the solvent used is 100 ml or less, the excessive use of the solvent is suppressed.

[Other ingredients]
When the compound (2) and the compound (3) are reacted, the compound (2), the compound (3), the base, and the solvent are all applicable as long as the effects of the present invention are not impaired. Other ingredients may be used.
The type of the other component is not particularly limited and can be arbitrarily selected depending on the intended purpose.

When the other component is used, 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.

When the other component is used, the amount of the other component used is not particularly limited and can be arbitrarily selected according to the type of the other component.

[Other reaction conditions]
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.

In the present embodiment, after completion of the reaction, if necessary, post-treatment is carried out by a known method, and then compound (1) can be taken out by a known method.
For example, after completion of the reaction, 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.
When another step using compound (1) is to be continued after the reaction is completed, after the reaction is completed, 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.

When a plurality of types of the compound (1) are produced by the reaction of the compound (2) and the compound (3), one or both of the above-mentioned post-treatment operation and purification operation should be appropriately selected and 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.

<< Compound >>
The compound according to one embodiment of the present invention has the following general formula (10):

(In the formula, p ₁ is 0, 1 or 2; 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. In some cases, these groups may be bonded to each other to form a ring.)
(However, 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". 4-CH ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ", formula" -Si ((4-CBr ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ", formula" -Si ((4-COOH)) C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ ) ”, formula“ -Si (CH ₃ ) ₂ (CH = CH ₂ ) ”, formula“ -Si (CH = CH ₂ ) ₃ ", the formula" -Si (CH ₃ ) ₂ CH ₂ Cl ", or the group represented by the _{formula" -Si (CH 3} ) ₂ (OSi (CH ₃ ) _{3) "} A compound, a compound in which p ₁ is 1, seven Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ", and one Z ¹⁰ is a hydrogen atom, and p ₁ Is 1, 6 Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ^{", 2 Z 10s} are hydrogen atoms, and p ₁ is 1 and 5 number of ^{Z 10} is the formula "-Si _{(CH 3) 3"} is a group represented by, except three ^{Z 10} is a compound which is a hydrogen atom, a).

The compound of the present embodiment (in this specification, may be referred to as "compound (10)") can be used as a functional silicon material and is highly useful.

In the general formula (10), _{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. A ^{compound in which all Z 10s} are groups represented by the formula "-Si (CH ₃ ) _{2 H" and p 1} is 1, and ^{all eight Z 10s} are all represented by the formula "-Si ((4-CH ₃ )). The compound which is the group represented by " _{C 6} H ₄ ) (CH ₃ ) _{2 ", p 1} is 1, and ^{all eight Z 10s} are of the formula "-Si ((4-CBr ₃ ) C ₆ H _4". ) (CH ₃ ) ₂ ”, p ₁ is 1, and ^{all eight Z 10s} are of the formula“ −Si ((4-COOH) C ₆ H ₄ ) (CH ₃ ). It is the same as the compound (1) described above except that it does not contain the compound which is the group represented by "_2".
That is, _{the compound (10) when p 1} is 0 is represented by the following general formula (101), and _{the compound (10) when p 1} is 1 is represented by the following general formula (102). The compound (10) when p ₁ is 2 is represented by the following general formula (103).

(In the formula, Z ¹⁰ is the same as above.)

^{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 ". It does not form a group (4-carboxyphenyl (dimethyl) silyl group) "," When p ₁ is 1, ^{all eight Z 10s} are of the formula "-Si (CH ₃ ) ₂ (OSi (CH _{3 ) 3} ). ) ”,“ When p ₁ is 1, ^{all eight Z 10s} are groups represented by the formula “−Si (CH ₃ ) ₂ (CH = CH _2)”. "When p ₁ is 1, ^{all eight Z 10s} are not groups represented by the formula" -Si (CH = CH ₂ ) _{3 "", "p 1} is 1. In some cases, ^{all eight Z 10s} are not groups represented by the formula "-Si (CH ₃ ) ₂ CH ₂ Cl""," 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 )"", "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. "," When p ₁ is 1, six 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).
For example, in the general formula (10), (2p ₁ + 6) 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.
For example, when ^{two or more (two or three) of 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).

As an example of the preferred compound (10), 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.

As an example of the more preferable compound (10), 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. ^{In R 10} , R ²⁰ and R ³⁰ of such compound (10), the alkyl group or aryl group may have a substituent.

As an example of a particularly preferable compound (10), the following general formula (1011): When _{p 1 is 0:}

(In the formula, 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 ^{When two or more of 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.
For example, when ^{two or more (two or three) of 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.

Further, as another example of the particularly preferable compound (10), when p ₁ is 1, the following general formula (1021):

^{(Wherein, 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".)
Compound represented by (where eight ^{Z 11} are all expressions "-Si _{(CH 3) 3",} the formula "-Si _{(CH 3) 2} H", the formula _{"-Si ((4-CH 3)} C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si ((4-CBr ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si ((4-COOH) C ₆ H ₄ ) ( CH ₃ ) ₂ ”, formula“ -Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ ) ”, formula“ -Si (CH ₃ ) ₂ (CH = CH ₂ ) ”, formula“ -Si (CH = CH) ₂ ) ₃ ", the compound which is the group represented by the formula" -Si (CH ₃ ) ₂ CH ₂ Cl ", or the formula" -Si (CH ₃ ) ₂ (OSi (CH ₃ ) _{3) ", and 7 pieces.} 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).

Further, as another example of the particularly preferable compound (10), when p ₁ is 2, the following general formula (1031):

^{(Wherein, 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 "-". The compound corresponding to the group represented by "Si (CH ₃ ) _{3 ", p 1} is 1, and ^{all eight Z 10s} are represented by the formula "-Si (CH ₃ ) _{2 H".} A compound corresponding to the group, p ₁ is 1, seven Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ", and one Z ¹⁰ is a hydrogen atom. A compound corresponding to a certain compound, p ₁ is 1, six Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ", and two Z ^10s are hydrogen atoms. Corresponds to a compound corresponding to, 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.

Hereinafter, the present invention will be described in more detail with reference to specific examples. However, the present invention is not limited to the examples shown below.

The meanings of the abbreviations used in this example are shown below.
DMAc: N, N-dimethylacetamide THF: tetrahydrofuran Me: Methyl group ⁿ Bu: n-Butyl group Ph: Phenyl group

The yield of compound (1) shown below is based on compound (2).
In the following, "mmol" represents " ^10-3 mol".
In the following, the names of the individual compounds of the compound (1) and the compound (2) are determined by using the reference numerals given to the formulas representing these compounds. For example, the "compound represented by the formula (1021) -1" described later is referred to as "compound (1021) -1".

<< Production of compound (1) >>
[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. From various NMR spectra of this suspension solution, it was confirmed that compound (1021) -1 (composition formula: Si ₁₆ O ₂₀ C ₄₈ H ₅₆ , "Si ₈ O ₁₂ [OSiPhH ₂ ] ₈ ") was produced. ..
Hexane (12 ml) was added to this suspension solution and the salt was filtered off. The obtained filtrate was washed with water, magnesium sulfate was added and dried, and then the filtrate was filtered off.
The solvent was distilled off from the obtained filtrate under reduced pressure, and then the low boiling point component was distilled off from the residue by Kugel lower distillation (8-18 Pa, 100 ° C., 1 hour) to make compound (1021) -1 colorless. Obtained as an oil (yield 258 mg, yield 86%).
The NMR data of the obtained compound (1021) -1 is shown below.

^{1 1} H-NMR (Benzene-d ₆ ): 5.20 ppm, 7.10 ppm, 7.54 ppm.
¹³ C-NMR (Benzene-d ₆ ): 128.4 ppm, 130.9 ppm, 133.0 ppm, 134.3 ppm.
²⁹ Si-NMR (Benzene-d ₆ ): -25.7 ppm, -107.8 ppm.

[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.
Hexane (6 ml) was added to this suspension solution and the salt was filtered off.
By distilling off the solvent from the obtained filtrate under reduced pressure, compound (1021) -2 was obtained as a solid (yield 80.0 mg, yield 77%).
The NMR data of the obtained compound (1021) -2 is shown below.

^{1 1} H-NMR (CDCl ₃ ): 0.26 ppm, 4.73 ppm.
¹³ C-NMR (CDCl ₃ ): 0.08 ppm.
²⁹ Si-NMR (CDCl ₃ ): −1.4 ppm, −108.7 ppm.

[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.
(29 mg, 0.02 mmol) of compound (22) -3 is dissolved in THF (0.5 ml), and the aniline solution (214 μl, 14.0 mg, 0.15 mmol as aniline) obtained above is added thereto. As a result, solution A was obtained.
Separately, THF (2 ml) and the chlorotrimethylsilane solution (219 μl, 16.3 mg as chlorotrimethylsilane, 0.15 mmol) obtained above were mixed to obtain a solution B.
At room temperature, solution B was added and reacted while stirring solution A. During this period, the reaction solution was initially transparent, but gradually became cloudy.
Twenty-three hours after the start of the reaction, the reaction solution was further added with the above-mentioned aniline solution (14 μl, 0.9 mg as aniline, 0.01 mmol) and the above-mentioned chlorotrimethylsilane solution (16 μl, chlorotrimethylsilane). As a major product, 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.

-Compound (1021) -3
^{1 1} H-NMR (THF-d ₈ ): 0.16 ppm.
¹³ C-NMR (THF-d ₈ ): 1.4 ppm.
²⁹ Si-NMR (THF-d ₈ ): 12.5 ppm, -109.0 ppm.
Compound (1021) -4
^{1 1} H-NMR (THF-d ₈ ): 0.16 ppm, 0.17 ppm.
¹³ C-NMR (THF-d ₈ ): 1.4 ppm, 1.4 ppm, 1.4 ppm.
²⁹ Si-NMR (THF-d ₈ ): 12.3 ppm, 12.4 ppm, 12.4 ppm, -100.8 ppm, -108.7 ppm, -108.8 ppm, -108.9 ppm.

[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. Since the presence of unreacted -SiOH moiety was confirmed from various NMR spectra of this suspension solution, aniline (439 mg, 6.00 mmol) and n-butylchlorodimethylsilane (904 mg, 6.00 mmol) were further added to room temperature. The suspension solution was obtained by stirring with the mixture for 16 hours. From the various NMR spectra of this suspension solution, it was confirmed that the reaction was completed and compound (1021) -5 (“Si ₈ O ₁₂ [OSiMe ₂ ⁿ Bu] _{8”) was produced.}
Hexane (40 ml) was added to this suspension solution and the salt was filtered off.
A colorless and transparent oil was obtained by distilling off the solvent from the obtained filtrate under reduced pressure. The oil was divided into two equal parts, each of which was dissolved in hexane (21 ml), and silica gel column chromatography was performed using hexane (250 ml) as a developing solvent. After fractionating 50 ml to 200 ml of the effluent, hexane was distilled off from this fraction under reduced pressure to obtain compound (1021) -5 as a colorless and transparent oil (yield 1.22 g, yield 83). %).
The NMR data of the obtained compound (1021) -5 is shown below.

^{1 1} H-NMR (CDCl ₃ ): 0.12 ppm, 0.59 ppm, 0.88 ppm, 1.33 ppm, 1.53 ppm.
¹³ C-NMR (CDCl ₃ ): -0.3 ppm, 13.8 ppm, 17.4 ppm, 25.1 ppm, 26.3 ppm.
²⁹ Si-NMR (CDCl ₃ ): 12.6 ppm, −108.9 ppm.

The present invention can be used as a functional silicon material or an intermediate thereof, and further as a method for producing these.

Claims (5)

1. The following general formula (2):
   

   

   (In the formula, p ₁ is 0, 1 or 2.)
   The compound represented by and the following general formula (3):
   

   

   (In the formula, 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.)
   By reacting with the compound represented by, the following general formula (1):
   

   

   (Wherein, ^{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, which comprises obtaining the compound represented by.
2. The following general formula (10):
   

   

   (In the formula, p ₁ is 0, 1 or 2; 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. In some cases, these groups may be bonded to each other to form a ring.)
   Compounds represented by (where p ₁ is 1 and ^{all eight Z 10s} are of the formula "-Si (CH ₃ ) ₃ ", of the formula "-Si (CH ₃ ) ₂ H", of the formula "-Si ( (4-CH ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ", formula" -Si ((4-CBr ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ", formula" -Si ((4-COOH) ) C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ ) ”, formula“ -Si (CH ₃ ) ₂ (CH = CH ₂ ) ”, formula A group represented by "-Si (CH = CH ₂ ) ₃ ", the formula "-Si (CH ₃ ) ₂ CH ₂ Cl", or the formula "-Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ )". A compound in which p ₁ is 1, seven Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ", and one Z ¹⁰ is a hydrogen atom, and p. ₁ is 1, 6 Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ^{", 2 Z 10s} are hydrogen atoms, and p ₁ is 1. (Excluding compounds in which 5 Z ^10s are groups represented by the formula "-Si (CH ₃ ) ₃ ^{" and 3 Z 10s} are hydrogen atoms).
3. The compound according to claim 2 ^{, wherein R 10} , R ²⁰ and R ³⁰ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
4. The compound according to claim 2 or 3, wherein R ¹⁰ , R ²⁰ and R ³⁰ are independently hydrogen atoms, alkyl groups having 1 to 6 carbon atoms or aryl groups having 6 to 12 carbon atoms.
5. The following general formula (1021):
   

   

   (In the formula, 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. 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 ^{When two or more of 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.)
   Compound represented by (where eight ^{Z 11} are all expressions "-Si _{(CH 3) 3",} the formula "-Si _{(CH 3) 2} H", the formula _{"-Si ((4-CH 3)} C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si ((4-CBr ₃ ) C ₆ H ₄ ) (CH ₃ ) ₂ ”, formula“ -Si ((4-COOH) C ₆ H ₄ ) ( CH ₃ ) ₂ ”, formula“ -Si (CH ₃ ) ₂ (OSi (CH ₃ ) ₃ ) ”, formula“ -Si (CH ₃ ) ₂ (CH = CH ₂ ) ”, formula“ -Si (CH = CH) ₂ ) ₃ ", the compound which is the group represented by the formula" -Si (CH ₃ ) ₂ CH ₂ Cl ", or the formula" -Si (CH ₃ ) ₂ (OSi (CH ₃ ) _{3) ", and 7 pieces.} 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 ^{Except for compounds in which 11} is a hydrogen atom).