6874-98-2

Basic information

• Product Name: C11634
• Synonyms: C11634;Sarpagan-17-al
• CAS NO: 6874-98-2
• Molecular Formula: C₁₉H₂₀N₂O
• Molecular Weight: 292.3749
• Mol File: 6874-98-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 305-306°
• Boiling Point: 434.31°C (rough estimate)
• Flash Point: 249.1°C
• Appearance: /
• Density: 1.1045 (rough estimate)
• Vapor Pressure: 1.1E-09mmHg at 25°C
• Refractive Index: 1.6140 (estimate)
• PKA: 17.62±0.40(Predicted)
• CAS DataBase Reference: C11634(CAS DataBase Reference)
• NIST Chemistry Reference: C11634(6874-98-2)
• EPA Substance Registry System: C11634(6874-98-2)

Safety Data

• Hazardous Substances Data: 6874-98-2(Hazardous Substances Data)

Usage

Description

C11634, also known as an indole alkaloid, is a chemical compound derived from sarpagan with an oxidized methyl group at position 16, forming a corresponding aldehyde. This modification gives C11634 unique properties that can be utilized in various applications.

Uses

Used in Pharmaceutical Industry:
C11634 is used as an active pharmaceutical ingredient for its potential therapeutic effects. The expression is: C11634 is used as an active pharmaceutical ingredient for its unique chemical properties and potential therapeutic applications.
Used in Chemical Research:
C11634 serves as a valuable compound in chemical research, particularly in the study of indole alkaloids and their derivatives. The expression is: C11634 is used as a research compound for the investigation of indole alkaloid chemistry and the development of novel chemical entities.
Used in Drug Synthesis:
C11634 can be employed as a key intermediate in the synthesis of other pharmaceutically relevant compounds. The expression is: C11634 is used as a key intermediate in the synthesis of pharmaceutically relevant compounds due to its unique structural features.

InChI:InChI=1/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15?,17-,18-/m0/s1

Upstream product

• 6874-98-2 16-epi-vellosimine 
• 2520-44-7 (+)-polyneuridine aldehyde 
• 197143-13-8 (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 288141-10-6 (6S,10S)-(-)-9-oxo-12-((Z)-2'-iodo-2'-butenyl)-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 201221-36-5 (6S,10S)-(-)-9-oxo-12H-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 492454-63-4 3-ethylidene-13-methylene-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine 
• 288141-13-9 3-ethylidene-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-one 
• 126640-98-0 (E)-16-epi-normacusine B 
• 540731-68-8 (2S,6S,12bS)-3-Eth-(E)-ylidene-13-[1-methoxy-meth-(E)-ylidene]-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine 
• 288141-11-7 (6S,10S)-(-)-9-formyl-12-((Z)-2'-iodo-2'-butenyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cycloocta[b]indole 
• 88199-28-4 16-epi-vellosimine 
• 639-36-1 E-akuammidine 
• 2520-44-7 (2S,6S,13S)-3-Eth-(E)-ylidene-13-formyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine-13-carboxylic acid methyl ester 
• 124016-70-2 C₂₆H₃₄N₂O₆ 

Downstream Products

• 604-99-9 10-de oxy-sarpagine 
• 34020-07-0 vinorine 
• 6874-98-2 (+)-vellosimine 
• 482-68-8 Sarpagine 
• 1358-75-4 (+)-3-ethylidene-1,3,4,7,12,12b-hexahydro-13-hydroxymethyl-2H,6H-2,6-methanoindolo[2,3-a]quinolizine 
• 604-99-9 10-deoxysarpagine 
• 604-99-9 16-epi-Koumidine 

Relevant articles and documents

General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine

matrix presented (+)-Vellosimine has been synthesized enantiospecifically in 27% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled intramolecular palladium-coupling reaction as key steps.

Stereospecific total synthesis of the indole alkaloid ervincidine. Establishment of the C-6 hydroxyl stereochemistry

The total synthesis of the indole alkaloid ervincidine (3) is reported. This research provides a general entry into C-6 hydroxy-substituted indole alkaloids with either an α or a β configuration. This study corrects the errors in Glasby's book (Glasby, J. S. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975) and Lounasmaa et al.'s review (Lounasmaa, M.; Hanhinen, P.; Westersund, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1999; Vol. 52, pp 103-195) as well as clarifies the work of Yunusov et al. (Malikov, V. M.; Sharipov, M. R.; Yunusov, S. Yu. Khim. Prir. Soedin. 1972, 8, 760-761. Rakhimov, D. A.; Sharipov, M. R.; Aripov, Kh. N.; Malikov, V. M.; Shakirov, T. T.; Yunusov, S. Yu. Khim. Prir. Soedin. 1970, 6, 724-725). It establishes the correct absolute configuration of the C-6 hydroxyl function in ervincidine. This serves as a structure proof and corrects the misassigned structure reported in the literature.

First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridme and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A

(Chemical Equation Presented) The first enantiospecific total synthesis of the alkaloids 16-epi-vellosimine (1), (+)-polyneuridine (2), (+)-polyneuridine aldehyde (3), and macusine A (4) is reported. The key oxidation was accomplished with the Corey-Kim reagent to provide the important biogenetic intermediates, 16-epi-vellosimine (1) and polyneuridine aldehyde (3), the latter of which is required for the conversion of the sarpagan skeleton into the ajmalan system in the biosynthesis of quebrachidine.