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19452-84-7

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19452-84-7 Usage

Description

An alkaloid which occurs in Tabernaemontana psychotrifolia H.B.K., this base is laevorotatory having [α]>D - 243° and gives an ultraviolet spectrum with absorption maxima at 222, 2S0 and 296 mp. with a shoulder at 272 mil. The alkaloid may be purified by recrystallization from Me2CO followed by sublima_x0002_tion. It yields a crystalline methiodide, m.p. 272-4°C (dec.) which has an ultraviolet spectrum containing an absorption maximum at 222 mp. and a shoulder at 276 mp.. On catalytic hydrogenation with Pt02 as catalyst it gives the dihydro derivative, m.p. 191-3°C, furnishing a methiodide, m.p. 265-SoC (dec.). Zn dust distillation yields 3-ethylpyridine and 3-methyl-5-ethylpyridine.

References

Benoin, Burnell, Medina., Tetrahedron Lett., 807 (1968) Burnell, Medina., Can. J. Chem., 49,307 (1971)

Check Digit Verification of cas no

The CAS Registry Mumber 19452-84-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,4,5 and 2 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 19452-84:
(7*1)+(6*9)+(5*4)+(4*5)+(3*2)+(2*8)+(1*4)=127
127 % 10 = 7
So 19452-84-7 is a valid CAS Registry Number.

19452-84-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (19Z)-Anhydrovobasinediol

1.2 Other means of identification

Product number -
Other names (19Z)-taberpsychine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:19452-84-7 SDS

19452-84-7Downstream Products

19452-84-7Relevant articles and documents

Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N4-Oxide

Kerkovius, Jeff K.,Kerr, Michael A.

, p. 8415 - 8419 (2018)

We report the total synthesis of the natural products isodihydrokoumine and (19Z)-taberpsychine in 11 steps each and (4R)-isodihydrokoumine N4-oxide in 12 steps from commercially available starting materials. The key reactions include an intramolecular [3 + 2] nitrone cycloaddition and Lewis acid mediated cyclizations of a common intermediate to provide the core structures of either taberpsychine or isodihydrokoumine.

Studies on Gelsemium alkaloids. Total synthesis of (+)-koumine, (+)-taberpsychine, and (+)-koumidine

Magnus, Philip,Mugrage, Benjamin,DeLuca, Mark R.,Cain, Gary A.

, p. 5220 - 5230 (2007/10/02)

The total synthesis of the Gelsemium alkaloids (+)-koumine (2), (+)-taberpsychine (4), and (+)-koumidine (50) has been accomplished starting from (S)-(-)-tryptophan (21), All the synthetic alkaloids are antipodal to the natural compounds. N′ -Benzyltryptophan ((-)-22) was methylated to give 23 which was reductively benzylated to provide (-)-25. Pictet-Spengler condensation of (-)-25 with 2-ketoglutaric acid followed by esterification gave a mixture of diastereomeric methyl esters 27/28. Exposure of (+)-27 and (-)-28 to Dieckmann cyclization conditions provided (+)-29 and (-)-29, respectively. Thus starting from a single enantiomer of tryptophan both antipodes of the tetracyclic β-ketoesters (+)-29/(-)-29 are available. Since (+)-29 was the more readily available antipode, subsequent reactions were conducted with this compound. Conversion of (+)-29 into (+)-31 followed conventional lines. N-Alkylation of (+)-31 with propargyl bromide gave (+)-33 which was converted into (+)-36 by treatment with t-BuMe2SiOTf/Et3N, n-BuLi/CICO2Me, and LiBF4. Exposure of (+)-36 to pyrrolidine/ trifluoroacetic acid gave the (Z)- and (E)-quinuclidines (+)-37 and (+)-38. Methylenation of 38 with Tebbe's reagent gave 39. Both E and Z isomers were taken through the series of transformations to give 43, 45, 47, and 49 and 44, 46, 48, and 50. The structures of (+)-37 and (+)-43 were conclusively established by single-crystal X-ray crystallography. Fragmentation of 49 with methyl chloroformate gave 51 which was reduced with LiAlH4 to give (+)-taberpsychine (4). Treatment of 47 with methyl chloroformate gave the 18-hydroxytaberpsychine derivative 52 which was reduced with LiAlH4 to give 53. Similarly 48 gave 55. When the Z isomer 55 was exposed to the Mitsunubo conditions, (+)-koumine (2) was formed (40%, 72% based upon recovered 55). The E isomer 53 gave (+)-koumine (2) in lower yields at a much reduced rate.

Total synthesis of (+)-koumine, (+)-taberpsychine, and (+)-koumidine

Magnus,Mugrage,DeLuca,Cain

, p. 786 - 789 (2007/10/02)

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