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YoehlmotoOhta, Teutomu Sakai and Yoehio Hiroee
The
Inetltute
Of Food Chemistry
Dojimanaka,Kita-ku,Oeaka, Japan
(Received 25 August 1966; in revised form 21 October 1966)
I-OT
411
6365
6366
No.51
-20.0(c,0.874 In chloro-
spectrum:hmax208~
'I-Methyl
cadalene(VI) was derived
6367
No.51
I.
I1
zm
*.
lm
1..
-cllf
no0
end Ct7)-CH3),2.58
(3H 6.1, 7.13 (2H 8. Ha), 7.69 (lH, Hc) and 7.84ppm (lH, Hb),
and the double bond in a-cubebenewas proved to be at C 6-7.
The locationof cyclopropanering was proved by the following reactions.
6 2.0-2.5ppmmeans that there is only one methylenegroup adjacent to carbonylor methoxycerbonylgroup and no proton on
$-carbonatom to carbonylgroup.
The remarkablyabundant
6368
ion
~pe&s,
No.51
VII
VIII
The com-
pound has a terminalmethylenegroup conjugatedwith a cyclopropane ring and no methyl group attachedto C=C double bond,
tm
@cd
No.51
6369
of
hmax21~
(E, 4,340).
(1)
(2)
column coated with polypropylene glycol at 150, it was partially isomerized to a-cubebene.
(3)
By passing through a
(4)
On hydrogenation with
As it showed hmax209mt.I
(E, 2,210) in W,
conjugation
No.51
6570
92 0928).
Se,&,
2, R.K.Razdenand S.C.Bhattacharyga,
66 (1952).
3, P. de Mayo, R.E. Williama,0. Btlchland S.R. Feaix'heller,
Tetrabdron, y,
619 (1965).
607 (1965).
ai, 9:t.g
(1960).
6, L.R. Brigge end W.I. Taylor, J. Chem. Sot., 1338 (1947).