Chanoclavine

Base Information

• Chemical Name: Chanoclavine
• CAS No.: 2390-99-0
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.348
• UNII: 32X6F73RE2
• DSSTox Substance ID: DTXSID50893242
• Metabolomics Workbench ID: 53062
• Nikkaji Number: J10.335G
• Wikidata: Q15410883
• Wikipedia: Chanoclavine
• Mol file: 2390-99-0.mol

Synonyms:(4R-(4alpha,5alpha(E)))-isomer of chanoclavine;(4R-(4alpha,5beta(Z)))-isomer of chanoclavine;chanoclavin-I;chanoclavine;isochanoclavin

Chemical Property of Chanoclavine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 220-222°
• Boiling Point: 470.1°Cat760mmHg
• Flash Point: 238.1°C
• PSA: 48.05000
• Density: 1.19g/cm³
• LogP: 2.72510
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 256.157563266
• Heavy Atom Count: 19
• Complexity: 355

Purity/Quality:

99%, ^*data from raw suppliers

(R,R)-Chanoclavine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1C(CC2=CNC3=CC=CC1=C23)NC)CO
• Isomeric SMILES: C/C(=C\[C@H]1[C@@H](CC2=CNC3=CC=CC1=C23)NC)/CO
• Uses: (R,R)-Chanoclavine is a modified ergot alkaloid produced by fungus. Stimulates dopamine receptors in the brain in rodents.

Technology Process of Chanoclavine

There total 152 articles about Chanoclavine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-methoxycarbonylamino-1,3,4,5-tetrahydrobenz[cd]indole (106507-95-3,106566-47-6,111467-77-7,118760-11-5) → (+/-)-chanoclavine I (1150-43-2,1150-44-3,1466-08-6,2390-99-0,57550-19-3,76109-09-6,109668-52-2,111427-26-0,118760-09-1,11012-16-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

Reference yield: 95.0%

(E)-3-((4S,5S)-4-Methoxycarbonylamino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-2-methyl-acrylic acid methyl ester (133738-27-9) → (+/-)-chanoclavine I (1150-43-2,1150-44-3,1466-08-6,2390-99-0,57550-19-3,76109-09-6,109668-52-2,111427-26-0,118760-09-1,11012-16-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.3987/COM-90-5577

Reference yield: 90.0%

N-((4R,5R)-5-((E)-3-hydroxy-2-methylprop-1-en-1-yl)-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)-N,4-dimethylbenzenesulfonamide → chanoclavine (2390-99-0,11012-16-1)

Guidance literature:

With naphthalene; sodium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03683

upstream raw materials:

methyl-(E)-3<(4R,5R)-1-tert-butoxycarbonyl-4-(N-tert-butoxycarbonylamino)-1,3,4,5-tetrahydrobenzindol-5-yl>-2-methylpropenoate

[(4R,5R)-5-((E)-3-Hydroxy-2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid methyl ester

(-)-4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole

(E)-3-((4R,5R)-4-Amino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-2-methyl-prop-2-en-1-ol

Downstream raw materials:

(+/-)-Agroclavine

(+/-)-Agroclavine I

Pyroclavin

festuclavine

Refernces

• 1、 Chaudhuri, Saikat,Bhunia, Subhajit,Roy, Avishek,Das, Mrinal K.,Bisai, Alakesh. "Biomimetic Total Syntheses of Clavine Alkaloids". supporting information. p. 288 - 291. Retrieved 2018/01/17.
• 2、 Yamada, Fumio,Makita, Yoshihiko,Somei, Masanori. "Synthetic studies directed toward ergot alkaloids, (±)-6,7-secoagroclavine, (±)-chanoclavine-1, (±)-chanoclavine-II, and (±)-agroclavine-I, by an efficient and common synthetic route". . p. 599 - 620. Retrieved 2008/03/12.