6,11-alpha(H)-Santonin

Base Information

• Chemical Name: 6,11-alpha(H)-Santonin
• CAS No.: 1618-78-6
• Molecular Formula: C15H18 O3
• Molecular Weight: 246.306
• DSSTox Substance ID: DTXSID40859397
• Nikkaji Number: J38.669C
• Wikidata: Q105328951
• ChEMBL ID: CHEMBL4228721
• Mol file: 1618-78-6.mol

Synonyms:Santonin C;6,11-alpha(H)-Santonin;1618-78-6;CHEMBL4228721;DTXSID40859397

Chemical Property of 6,11-alpha(H)-Santonin

Chemical Property:

• Boiling Point: 423.4°Cat760mmHg
• Flash Point: 189.7°C
• PSA: 43.37000
• Density: 1.18g/cm³
• LogP: 2.41960
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 500

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC3(C=CC(=O)C(=C3C2OC1=O)C)C
• Isomeric SMILES: C[C@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@@H]2OC1=O)C)C

Technology Process of 6,11-alpha(H)-Santonin

There total 98 articles about 6,11-alpha(H)-Santonin 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: 61.0%

santonin (481-06-1) → 6-epi-α-Santonin (1618-78-6)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; at 100 ℃; for 1h;

DOI:10.1021/jo00267a049

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) + α-Santonin (481-06-1,481-07-2,1618-77-5,1618-78-6,3650-48-4,21295-21-6,64912-47-6,64912-48-7,135270-27-8,135270-28-9) → (+/-)-α-Desmotroposantonin (438-50-6,13743-88-9,13743-89-0,13743-96-9,16963-59-0,21142-64-3,5951-46-2) + (+/-)-Santonin-C (481-06-1,481-07-2,1618-77-5,1618-78-6,3650-48-4,21295-21-6,64912-47-6,64912-48-7,135270-27-8,135270-28-9)

Guidance literature:

Reference yield:

rac-11-methyl-3-oxo-eudesm-4-ene-12,13-dioic acid diethyl ester (102315-35-5) → (+/-)-Santonin-D (481-06-1,481-07-2,1618-77-5,1618-78-6,3650-48-4,21295-21-6,64912-47-6,64912-48-7,135270-27-8,135270-28-9)

Guidance literature:

Multi-step reaction with 7 steps

1: aq.-ethanolic KOH

2: diethyl ether; bromine

3: aqueous sodium hydrogencarbonate solution

4: diethyl ether; bromine

5: 5-ethyl-2-methyl-pyridine

6: aqueous KOH-solution / Erwaermen der Reaktionsloesung mit wss. Salzsaeure

7: 2,4,6-trimethyl-pyridine

With 2,4,6-trimethyl-pyridine; 5-ethyl-2-methyl-pyridine; potassium hydroxide; diethyl ether; bromine; sodium hydrogencarbonate;

upstream raw materials:

(+)-2-(1,2,3,4,4a,5,6,7-octahydro-4a,8-dimethyl-7-oxo-2-naphthyl)-propionic acid

santonin

hydrogenchloride

N,N-dimethyl-formamide

Downstream raw materials:

(-)-dictyolene

Toluene-4-sulfonic acid (S)-2-((1R,2S,4aS,8aR)-4a,8-dimethyl-1-trimethylsilanyloxy-1,2,3,4,4a,8a-hexahydro-naphthalen-2-yl)-propyl ester

2-((2R,4aR,5S)-4a,8-Dimethyl-7-oxo-5-phenylselanyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-propionic acid methyl ester

rac-(11R)-6β-hydroxy-3-oxo-eudesma-1,4-dien-12-oic acid