(4S,6'S,11R)-6'-Ethyl-2,3,4,5,5',6,6',7,8,8aα,9α,10-dodecahydro-6'-methoxy-2-methylspiro[1H-4,10aα-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]-pyran]-9-carboxylic acid methyl ester

CAS No.
54370-35-3
Chemical Name:
(4S,6'S,11R)-6'-Ethyl-2,3,4,5,5',6,6',7,8,8aα,9α,10-dodecahydro-6'-methoxy-2-methylspiro[1H-4,10aα-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]-pyran]-9-carboxylic acid methyl ester
Synonyms
Yuzurine;(4S,6'S,11R)-6'-Ethyl-2,3,4,5,5',6,6',7,8,8aα,9α,10-dodecahydro-6'-methoxy-2-methylspiro[1H-4,10aα-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]-pyran]-9-carboxylic acid methyl ester;Spiro[1H-4,10a-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]pyran]-9-carboxylic acid, 6'-ethyl-2,3,4,5,5',6,6',7,8,8a,9,10-dodecahydro-6'-methoxy-2-methyl-, methyl ester, (3'R,4S,6'S,8aR,9R,10aR)-
CBNumber:
CB52250154
Molecular Formula:
C24H37NO4
Molecular Weight:
403.56
MDL Number:
MOL File:
54370-35-3.mol

(4S,6'S,11R)-6'-Ethyl-2,3,4,5,5',6,6',7,8,8aα,9α,10-dodecahydro-6'-methoxy-2-methylspiro[1H-4,10aα-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]-pyran]-9-carboxylic acid methyl ester Properties

Boiling point 506.1±50.0 °C(Predicted)
Density 1.16±0.1 g/cm3(Predicted)
pka 9.16±0.60(Predicted)

(4S,6'S,11R)-6'-Ethyl-2,3,4,5,5',6,6',7,8,8aα,9α,10-dodecahydro-6'-methoxy-2-methylspiro[1H-4,10aα-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]-pyran]-9-carboxylic acid methyl ester Chemical Properties,Uses,Production

Description

This complex alkaloid, obtained from Daphniphyllum macropodum, is a liquid but forms a crystalline methiodide with m.p. 229-230°C. The structure has been determined by chemical and spectroscopic methods.

References

Toda, Hirata, Yamamura, Tetrahedron, 28, 1477 (1972) Structure: Yamamura et ai., Tetrahedron Lett., 2023 (1974)

(4S,6'S,11R)-6'-Ethyl-2,3,4,5,5',6,6',7,8,8aα,9α,10-dodecahydro-6'-methoxy-2-methylspiro[1H-4,10aα-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]-pyran]-9-carboxylic acid methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

(4S,6'S,11R)-6'-Ethyl-2,3,4,5,5',6,6',7,8,8aα,9α,10-dodecahydro-6'-methoxy-2-methylspiro[1H-4,10aα-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]-pyran]-9-carboxylic acid methyl ester Yuzurine Spiro[1H-4,10a-methanopentaleno[1,6-cd]azonine-11,3'(4'H)-[2H]pyran]-9-carboxylic acid, 6'-ethyl-2,3,4,5,5',6,6',7,8,8a,9,10-dodecahydro-6'-methoxy-2-methyl-, methyl ester, (3'R,4S,6'S,8aR,9R,10aR)- 54370-35-3