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(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one

(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one ??? ???
?? ??:
2810-21-1
???:
(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one
???(??):
Stepharine;(+)-Stepharine;(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one;(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one;Spiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-, (8'aR)-
CBNumber:
CB52323100
???:
C18H19NO3
??? ??:
297.34836
MOL ??:
2810-21-1.mol

(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one ??

???
179-181 °C
?? ?
487.1±45.0 °C(Predicted)
??
1.27±0.1 g/cm3(Predicted)
?? ??
4°C, protect from light
??? ??
Solid
?? ?? (pKa)
8.08±0.20(Predicted)
??
Pale purple to purple

??

(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one C??? ??, ??, ??

??

A spiroisoquinoline alkaloid from Stephania glabra, the base has [α]26D + 143° (c 1.88, CHCI3). It contains two methoxyl groups and an imino group and yields a crystalline N-acetyl derivative, m.p. 234-5°C; [α]24D- 80° (c 1.57, CHCI3). The N-methyl compound has been shown to be identical with Pronuciferine (q.v.).

?? ??

Cava et al., Chern. Ind., 282 (1964)
Tomita et al., Tetrahedron Lett., 2825 (1965)
Baldwin et al., J. Chern. Soc., C, 154 (1967)
Circular dichroism: Snatzke, Wollenberg., J. Chern. Soc., C, 1681 (1966)

(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one ?? ?? ? ???

???

?? ??


(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one ?? ??

???( 17)?? ??
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