Isochanoclavine I

Base Information

• Chemical Name: Isochanoclavine I
• CAS No.: 1150-44-3
• Deprecated CAS: 11014-19-0
• Molecular Formula: C16H20 N2 O
• Molecular Weight: 256.348
• UNII: K0POV5NPT2
• Nikkaji Number: J13.849E
• Wikidata: Q105248854
• Mol file: 1150-44-3.mol

Synonyms:Isochanoclavine I;Isochanoclavin-I;Isochanoclavine;K0POV5NPT2;UNII-K0POV5NPT2;1150-44-3;(+/-)-Isochanoclavine I;(Z)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol;2-Propen-1-ol, 2-methyl-3-(1,3,4,5-tetrahydro-4-(methylamino)benz(cd)indol-5-yl)-, (4R-(alpha,5beta(Z)))-;(-)-ISOCHANOCLAVINE I;SCHEMBL1259353;2-PROPEN-1-OL, 2-METHYL-3-((4R,5R)-1,3,4,5-TETRAHYDRO-4-(METHYLAMINO)BENZ(CD)INDOL-5-YL)-, (2Z)-

Chemical Property of Isochanoclavine I

Chemical Property:

• PSA: 48.05000
• 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:

98%,99%, ^*data from raw 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

Technology Process of Isochanoclavine I

There total 104 articles about Isochanoclavine I 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: 88.0%

C30H32N2O5S2 → (+)-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 naphthalene; sodium; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03683

upstream raw materials:

[(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

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

Downstream raw materials:

agroclavine

(+/-)-Agroclavine I

(+/-)-Agroclavine

Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester

Refernces

• 1、 Lu, Jia-Tian,Shi, Zi-Fa,Cao, Xiao-Ping. "Total Synthesis of (-)-Chanoclavine i and an Oxygen-Substituted Ergoline Derivative". supporting information. p. 7774 - 7782. Retrieved 2017/08/14.
• 2、 Somei, Masanori,Nakagawa, Kyoko. "Simple total syntheses of (-)-ergot alkaloids and their (+)-enantiomers by a common synthesis method utilizing optical resolution". . p. 1263 - 1266. Retrieved 2007/10/03.