Hydroxymethyl-group-containing alicyclic compound and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

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C562S123000, C562S830000, C568S816000, C568S830000

Reexamination Certificate

active

06576787

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel hydroxymethyl-group-containing alicyclic compound which is useful as a monomer or a material thereof for photosensitive resins and other functional polymers, to a process for producing the same, and to a polymerizable alicyclic compound.
BACKGROUND ART
Alicyclic compounds each having a hydroxymethyl group are used as, for example, monomers or materials thereof for resist resins, and as intermediates of pharmaceuticals, and have received attention in recent years.
However, neither alicyclic compound nor ester of this compound with a carboxylic acid having a polymerizable unsaturated group is known, which alicyclic compound has a polycyclic carbon ring with two or three non-aromatic carbon rings each commonly possessing two carbon atoms and has a 1-(mono- or di-) substituted hydroxymethyl group combined with a carbon atom at a junction position between two rings.
DISCLOSURE OF INVENTION
Accordingly, it is an object of the present invention to provide an alicyclic compound having a polycyclic carbon ring with two or three non-aromatic carbon rings each commonly possessing two carbon atoms, and having a 1-(mono- or di-)substituted hydroxymethyl group combined with a carbon atom at a junction position between two rings, and to provide a process for producing the same.
Another object of the present invention is to provide an ester of the aforementioned alicyclic compound with a carboxylic acid having a polymerizable unsaturated group.
After intensive investigations to achieve the above objects, the present inventors found that a novel hydroxymethyl-group-containing alicyclic compound having an introduced specific substituent at a carbon atom adjacent to a hydroxyl group (&agr;-position carbon atom) can be obtained by allowing an organometallic compound to act upon a polycyclic alicyclic compound having an acyl group, a carboxyl croup or a substituted oxycarbonyl group at a junction position. They further found that a novel polymerizable alicyclic compound can be obtained by allowing the aforementioned compound to react with a carboxylic acid having a polymerizable unsaturated group or a derivative thereof. The present invention has been accomplished based on these findings.
Specifically, the present invention provides a hydroxymethyl-group-containing alicyclic compound represented by the following formula (1) or (2):
[wherein each of ring A, ring B, ring C, ring D, and ring E is a non-aromatic carbon ring; each of R
a
and R
b
is, identical to or different from each other, a hydrogen atom or a hydrocarbon group, and at least either of R
a
and R
b
is a hydrocarbon group; and each of R
c
, R
d
, and R
e
is a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, an amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a nitro group, an acyl group, or a group represented by the following formula (3):
(wherein R
a
and R
b
have the same meanings as defined above.)]
In this compound, each of the ring A, ring B, ring C, ring D, and ring E may be a cyclopentane ring, a cyclohexane ring, or a bridged ring. Polycyclic carbon rings formed by the ring A and ring B or by the ring C, ring D and ring E in the formula (1) or (2) include, for example, a perhydroindene ring, a decalin ring, a perhydrofluorene ring, a perhydroanthracene ring, a perhydrophenanthrene ring, a tricyclo[5.2.1.0
2,6
]decane ring, a perhydroacenaphthene ring, and a perhydrophenalene ring.
The present invention provides, in another aspect, a process for producing a hydroxymethyl-group-containing alicyclic compound (hereinafter simply referred to as “production process 1”). This process includes the step of allowing an acyl-group-containing alicyclic compound represented by the following formula (4) or (5):
(wherein each of ring A, ring B, ring C, ring D, and ring E is a non-aromatic carbon ring; R
x
is a hydrogen atom or a hydrocarbon group; and each of R
c1
, R
d1
, and R
e1
is a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, an amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a nitro group, or an acyl group) to react with an organometallic compound represented by the following formula (6):
R
y
—M  (6)
[wherein R
y
is a hydrogen atom or a hydrocarbon group, where R
y
is a hydrocarbon group when R
x
in the formula (4) or (5) is a hydrogen atom; and M is a metal atom which may have a ligand, or a group represented by the following formula (7):
—MgY  (7)
(wherein Y is a halogen atom)] to yield the compound represented by the formula (1) or (2).
In a further aspect, the present invention provides a process for producing a hydroxymethyl-group-containing alicyclic compound (hereinafter simply referred to as “production process 2”). This process includes the step of allowing an alicyclic carboxylic acid derivative represented by the following formula (8) or (9):
(wherein each of ring A, ring B, ring C, ring D, and ring E is a non-aromatic carbon ring; R
z
is a hydrogen atom or a hydrocarbon group which may have a substituent; and each of R
c1
, R
d1
, and R
e1
is a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, an amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a nitro group, or an acyl group) to react with an organometallic compound represented by the following formula (6a):
R
a1
—M  (6a)
[wherein R
a1
is a hydrocarbon group; and M is a metal atom which may have a ligand, or a group represented by the following formula (7):
—MgY  (7)
(wherein Y is a halogen atom)] to yield a compound represented by the following formula (1a) or (2a):
[wherein ring A, ring B, ring C, ring D, ring E and R
a1
have the same meanings as defined above; and each of R
c
, R
d
, and R
e
is a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, an amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a nitro group, an acyl group, or a group represented by the following formula (3a):
(wherein R
a1
has the same meaning as defined above)].
In addition, the present invention provides a polymerizable alicyclic compound represented by the following formula (10) or (11):
[wherein each of ring A, ring B, ring C, ring D, and ring E is a non-aromatic carbon ring; R is a polymerizable unsaturated group; each of R
a
and R
b
is, identical to or different from each other, a hydrogen atom or a hydrocarbon group, where at least either of R
a
and R
b
is a hydrocarbon group; and each of R
c2
, R
d2
, and R
e2
is a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group which may be protected by a protective group, a hydroxymethyl group which may be protected by a protective group, an amino group which may be protected by a protective group, a carboxyl group which may be protected by a protective group, a nitro group, an acyl group, or a group represented by the following formula (12):
(wherein R
f
is a hydrogen atom or an RC(═O) group (where R has the same meaning as defined above); and R
a
and R
b
have the same meanings as defined above)].
In this compound, each of the ring A, ring B, ring C, ring D, and ring E may be a cyclopentane ring, a cyclohexane ring, or a bridged ring. Polycyclic carbon rings formed by the ring A and ring B, or by the ring C, ring D and ring E in the formula (10) or (11) incl

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