Bicycle lactones, perfumery uses thereof, processes for preparing same and intermediates therefor

A perfumed article comprising a perfumed article base and an aroma augmenting, enhancing or imparting quantity and concentration of a bicyclic lactone having a structure selected from the group consisting of:

• 209
• wherein Z is a moiety selected from the group consisting of:
• 210
• and wherein one of R1 or R3 is methyl and the other is hydrogen;
• wherein R4, R5, R6, R7, R8 and R9 are hydrogen or nonadjacent C1-C3 alkyl;
• wherein Y is C2-C12 substituted or unsubstituted alkylidenyl, alkenylidenyl or alkadienylidenyl having the structure:
• 211
• and completes a C5-C15 cycloalkyl, cycloalkadienyl or cycloalkenyl ring moiety;
• wherein R12, R13, R14, R16, R17, R28, R29, R30 and R31 each represents hydrogen or C1-C3 nonadjacent alkyl;
• wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond;
• wherein s is an integer of from 0 up to 10;
• t is an integer of from 0 up to 10;
• wherein the sum of s and t is an integer of from 0 up to 10 defined according to the inequalities:
• 0≦s+t≦10;
• 0≦s≦10;
• and 0≦t≦10;
• and wherein v 1 or 2.

A perfumed polymer comprising a microporous polymer and contained in the interstices thereof an aroma augmenting, enhancing or imparting quantity and concentration of a bicyclic lactone having a structure selected from the group consisting of:

• 212
• wherein Z is a moiety selected from the group consisting of:
• 213
• and wherein one of R1 or R3 is methyl and the other is hydrogen;
• wherein R4, R5, R6, R7, R8 and R9 are hydrogen or nonadjacent C1-C3 alkyl;
• wherein Y is C2-C12 substituted or unsubstituted alkylidenyl, alkenylidenyl or alkadienylidenyl having the structure:
• 214
• and completes a C5-C15 cycloalkyl, cycloalkadienyl or cycloalkenyl ring moiety;
• wherein R12, R13, R14, R16, R17, R28, R29, R30 and R31 each represents hydrogen or C1-C3 nonadjacent alkyl;
• wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond;
• wherein s is an integer of from 0 up to 10;
• t is an integer of from 0 up to 10;
• wherein the sum of s and t is an integer of from 0 up to 10 defined according to the inequalities:
• 0≦s+t≦10;
• 0≦s≦10;
• and 0≦t≦10;
• and where in v 1 or 2.

A perfume composition comprising a perfume base and intimately admixed therewith an aroma augmenting, enhancing or imparting quantity of a bicyclic lactone having a structure selected from the group consisting of:

• 215
• wherein Z is a moiety selected from the group consisting of:
• 216
• and wherein one of R1 or R3 is methyl and the other is hydrogen;
• wherein R4, R5, R6, R7, R8 and R9 are hydrogen or nonadjacent C1-C3 alkyl;
• wherein Y is C2-C12 substituted or unsubstituted alkylidenyl, alkenylidenyl or alkadienylidenyl having the structure:
• 217
• and completes a C5-C15 cycloalkyl, cycloalkadienyl or cycloalkenyl ring moiety;
• wherein R12, R13, R14, R16, R17, R28, R29, R30 and R31 each represents hydrogen or C1-C3 nonadjacent alkyl;
• wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond;
• wherein s is an integer of from 0 up to 10;
• t is an integer of from 0 up to 10;
• wherein the sum of s and t is an integer of from 0 up to 10 defined according to the inequalities:
• 0≦s+t≦10;
• 0≦s≦10;
• and 0≦t≦10;
• and wherein v 1 or 2.

A bicyclic lactone having the structure:

• 218
• wherein Y is C2-C12 substituted or unsubstituted alkylidenyl, alkenylidenyl or alkadienylidenyl having the structure:
• 219
• and completes a C5-C15 cycloalkyl, cycloalkadienyl or cycloalkenyl ring moiety;
• wherein R12, R13, R14, R16, R17, R28, R29, R30 and R31 each represents hydrogen or C1-C3 nonadjacent alkyl;
• wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond;
• wherein s is an integer of from 0 up to 10;
• t is an integer of from 0 up to 10;
• wherein the sum of s and t is an integer of from 0 up to 10 defined according to the inequalities:
• 0≦s+t≦10;
• 0≦s≦10;
• and 0≦t≦10;
• and
• wherein v 1 or 2.

A ketoester having the structure:

• 221
• wherein Z is a moiety selected from the group consisting of:
• 222
• wherein R2 is C1-C4 lower alkyl;
• wherein one of R1 or R3 is methyl and the other is hydrogen;
• wherein R4, R5, R6, R7, R8 and R9 are hydrogen or nonadjacent C1-C3 alkyl.

An oxo-ester having the structure:

• 223
• wherein R15 is C1-C4 lower alkyl;
• wherein Y is C2-C12 substituted or unsubstituted alkylidenyl, alkenylidenyl or alkadienylidenyl having the structure:
• 224
• and completes a C5-C15 cycloalkyl, cycloalkadienyl or cycloalkenyl ring moiety;
• wherein R12, R13, R14, R16, R17, R28, R29, R30 and R31 each represents hydrogen or C1-C3 nonadjacent alkyl;
• wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond;
• wherein s is an integer of from 0 up to 10;
• t is an integer of from 0 up to 10;
• wherein the sum of s and t is an integer of from 0 up to 10 defined according to the inequalities:
• 0≦s+t≦10;
• 0≦s≦10;
• and 0≦t≦10;
• wherein v 1 or 2;
• and wherein R15 represents C1-C4 lower alkyl.

A process for the preparation of a bicyclic lactone comprising the steps of carrying out the reaction sequence in order:

• 225 226
• and isolating the resulting bicyclic lactone wherein Z is a moiety selected from the group consisting of:
• 227
• and wherein one of R1 or R3 is methyl and the other is hydrogen;
• wherein R4, R5, R6, R7, R8 and R9 are hydrogen or nonadjacent C1-C3 alkyl;
• and wherein R2 represents C1-C4 alkyl.

A process for the preparation of a bicyclic lactone comprising the steps of carrying out the reaction sequence in order:

• 228 229
• and isolating the resulting bicyclic lactone wherein wherein R15 is C1-C4 lower alkyl;
• wherein Y is C2-C12 substituted or unsubstituted alkylidenyl, alkenylidenyl or alkadienylidenyl having the structure:
• 230
• and completes a C5-C15 cycloalkyl, cycloalkadienyl or cycloalkenyl ring moiety;
• wherein R12, R13, R14, R16, R17, R28, R29, R30 and R31 each represents hydrogen or C1-C3 nonadjacent alkyl;
• wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond;
• wherein s is an integer of from 0 up to 10;
• t is an integer of from 0 up to 10;
• wherein the sum of s and t is an integer of from 0 up to 10 defined according to the inequalities:
• 0≦s+t≦10;
• 0≦s≦10;
• and 0≦t≦10;
• wherein v 1 or 2;
• and wherein R15 represents C1-C4 lower alkyl.