Compounds, functionalised dioxaborolane or dioxaborinane derivatives, method for preparing same and uses thereof

Patent metadata

Field	Value
Publication number	US-11279717-B2
Application number	US-201716306411-A
Country	US
Kind code	B2
Filing date	May 30, 2017
Priority date	May 30, 2016
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

The invention relates to functionalised dioxaborolane or dioxaborinane derivatives of formula (I), wherein R1 is covalently bonded to the boron atom by a carbon atom; one of R2, R3, R′3 or R4 is a radical of formula —X; or one of R1, R2, R3, R′3 or R4 is a radical of formula —X; and X is a functionalised radical. The invention relates to the method for preparing same and the uses thereof.

First claim

The invention claimed is:

1. A compound of formula (I)

with n=0 or 1,
R 1 is covalently linked to the boron atom by a carbon atom and represents a substituted or unsubstituted aryl group selected from a benzene ring, a naphthalene ring, an arylaliphatic group composed of two benzene rings linked by a C 1 -C 6 alkanediyl group, a pyridine ring, a pyrimidine ring and a triazine ring,
R′ 3 represents a hydrogen atom
R 4 represents a hydrogen atom or a group selected from alkyl, aryl, cycloalkyl, heteroaryl, heteroalkyl and heterocycloalkyl group,
R 3 represents a hydrogen atom or a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens, or together form, pairwise, an aliphatic or aromatic ring,
R 2 , R 3 , R 4 are not substituted by a radical of formula (I′),

with n i =0 or 1
R 2i , R 3i , R′ 3i , R 4i , identical or different, represent a hydrogen atom or a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens, or together form, pairwise, an aliphatic or aromatic ring,
R 2 represents a radical of formula —X,
X is selected from:
—(CH 2 ) m —CH(R 5 )—Y where Y is a maleimide, thiol, acrylamide, or a methacrylamide, m is an integer ranging from 0 to 12, R 5 is a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens;
—(CH 2 ) m —R 6 —Y where Y is a maleimide, thiol, —NH2, acrylamide, a methacrylamide, or a terminal alkene radical, m is an integer ranging from 0 to 12, R 6 is a hydrocarbon radical, substituted at least by Y, which may include one or more heteroatoms or halogens;
—(CH 2 ) r —Y, where Y is a maleimide, thiol, —NH2, acrylamide, a methacrylamide, or a terminal alkene radical, r is an integer ranging from 1 to 12;

with Het=—O—CO— or

 and R 7 is a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens, s is 0 or 1, t is 0 or 1, s+t=1 or 2;

with alk 1 , alk 2 , alk 3 each independently representing a linear or branched C 1 -C 4 alkyl and R 8 is a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens;

with R 9 is a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens and R 10 is a hydrogen atom, or a hydroxyl radical, or a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens;

the double bond is of cis or trans configuration, with R 11 is a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens, Z is a divalent group selected from —O—, —S—, or —NH—, Q is a C 1 -C 6 alkoxy radical or

 with Z′ is a divalent group selected from —O—, —S—, or —NH—, one of R″ 2 , R′″ 3 , R″ 3 , R″ 4 , R″ 1 is missing depending on the substitution site, R 12 is a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens, R″ 1 is covalently linked to the boron atom by a carbon atom and represents a substituted or unsubstituted hydrocarbon group which may include one or more heteroatoms or halogens, R″ 2 , R″ 3 , R′″ 3 , R″ 4 , identical or different, represent a hydrogen atom or a substituted or unsubstituted hydrocarbon radical which may include one or more heteroatoms or halogens, or together form, pairwise, an aliphatic or aromatic ring;

with R 13 is a substituted or unsubstituted hydrocarbon radical.

2. The compound according to claim 1 , wherein the radical R 1 represents aryl group selected from a benzene ring, a naphthalene ring, an arylaliphatic group composed of two benzene rings linked by a C1-C6 alkanediyl group, a pyridine ring, a pyrimidine ring and a triazine ring, said ring being unsubstituted or substituted from 1 to 3 times.

3. The compound according to claim 1 , wherein radical R 1 is substituted by functional groups selected from ester, amide, (meth)acrylate and styrene functions.

4. The compound according to claim 1 , wherein radical R 1 is substituted by a halogen, an -Rz, —OH, —NHRz, —NRzR′z, —C(O)—OH, —C(O)—NRzR′z, —C(O)—O-Rz, —O—C(O)-Rz, —O—C(O)—O-Rz, —O—C(O)—N(H)-Rz, —N(H)—C(O)—O-Rz, —O-Rz, —S-Rz, —C(O)—N(H)-Rz, or —N(H)—C(O)-Rz group with Rz, R′z, identical or different, representing a C 1 -C 50 alkyl radical.

5. The compound according to claim 1 , wherein R 4 represents H.

6. The compound according to claim 1 , wherein R 3 , represents H or —CH 3 .

7. The compound according to claim 1 , wherein R5 represents H or an unsubstituted hydrocarbon radical.

8. The compound according to claim 1 , wherein R6 represents a (hetero)alkanediyl, a (hetero)alkenediyl, a (hetero)aryl or a (hetero)cycloalkyl group.

9. The compound according to claim 1 , wherein r is an integer ranging from 1 to 4.

10. The compound according to claim 1 , wherein m is an integer ranging from 0 to 4.

11. The compound according to claim 1 , wherein said compound is selected from:

m, R 1 , R 2 , R 21 , R 3 , R′ 3 , R 31 , R′ 31 , R 4 , R 41 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R″ 2 , R″ 3 , R″ 4 , Het, alk 1 , alk 2 , alk 3 , s and t being as defined in claim 1 with i=1,
s′ is 0 or 1, t′ is 0 or 1, s′+t′=1 or 2,
Q is a C 1 -C 6 alkoxy radical,
R 51 has the same definition as that given for R 5 in claim 1 ,
R 61 has the same definition as that given for R 6 in claim 1 ,
R 71 has the same definition as that given for R 7 in claim 1 ,
R 81 has the same definition as that given for R 8 in claim 1 ,
R 91 has the same definition as that given for R 9 in claim 1 ,
R 101 has the same definition as that given for R 10 in claim 1 ,
R 131 has the same definition as that given for R 13 in claim 1 ,
Het 1 , Het 2 , identical or different, have the same definition as that given for Het in claim 1 ,
alk 11 , alk 21 , alk 31 , identical or different, have the same definition as that given for alk 1 , alk 2 , alk 3 in claim 1 ,
m 1 has the same definition

Assignees

• Ecole Superieure Physique & Chimie Ind Ville De Paris
• Centre Nat Rech Scient

Inventors

• Leibler Ludwik
• Nicolay Renaud

Classifications

• C07F5/025 Primary

  Boronic and borinic acid compounds · CPC title

• C07F7/1872

  Preparation; Treatments not provided for in C07F7/20 · CPC title

• C08G79/08

  a linkage containing boron · CPC title