CID 11024113

Base Information

• Chemical Name: CID 11024113
• CAS No.: 467-16-3
• Molecular Formula: C21H22N2O2
• Molecular Weight: 334.418
• Nikkaji Number: J1.631.624E
• Wikidata: Q105212280
• Metabolomics Workbench ID: 127056
• ChEMBL ID: CHEMBL2164628
• Mol file: 467-16-3.mol

Synonyms:Isostrychnine;CHEMBL2164628;CHEBI:132659;(1R,13S,14E,19S,21S)-14-(2-Hydroxyethylidene)-8,16-diazahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one;(1S)-3beta,1beta,11bbeta-[(E)-1-Hydroxy-5-aza-2-heptene-3,5,7-triyl]-1,2,3,5,11b,11cbeta-hexahydro-6H-pyrido[3,2,1-jk]carbazole-6-one;(3aR,11bS,12S,13aS,14E)-14-(2-hydroxyethylidene)-2,3,10,12,13,13a-hexahydro-9H,11bH-1,12-ethanopyrido[1,2,3-lm]pyrrolo[2,3-d]carbazol-9-one

Chemical Property of CID 11024113

Chemical Property:

• Vapor Pressure: 6.44E-14mmHg at 25°C
• Boiling Point: 571.9°Cat760mmHg
• Flash Point: 299.7°C
• Density: 1.41g/cm³
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 334.168127949
• Heavy Atom Count: 25
• Complexity: 698

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN2CC(=CCO)C3CC2C14C5C3=CCC(=O)N5C6=CC=CC=C46
• Isomeric SMILES: C1CN2C/C(=C/CO)/[C@@H]3C[C@H]2[C@@]14[C@@H]5C3=CCC(=O)N5C6=CC=CC=C46

Technology Process of CID 11024113

There total 45 articles about CID 11024113 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%

(-)-(21E)-12,13-didehydro-24-(tert-butyldimethylsilyl)-12,24-secostrychnidin-10-one (467222-58-8) → (+)-isostrychnine (467-16-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ja029382u

Reference yield:

strychnidin-10-one (57-24-9) → strychnine-N-oxide (7248-28-4) + (+)-isostrychnine (467-16-3)

Guidance literature:

at 235 ℃; Product distribution;

DOI:10.1248/cpb.38.1295

Reference yield:

(4aS,9aS)-4a-cyanomethyl-9-(4-methylbenzenesulfonyl)-2,4a,9,9a-tetrahydro-1H-carbazole (350677-99-5) → (+)-isostrychnine (467-16-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: LiAlH₄ / tetrahydrofuran / 1.5 h / 20 °C

2.1: 3.22 g / Et₃N / dimethylformamide / 1 h / 20 °C

3.1: 77 percent / MnO₂; benzoquinone; AcOH / Pd(OAc)2 / 20 h / 50 °C

4.1: 9-BBN / tetrahydrofuran / 9 h / 50 °C

4.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 4 h / 20 °C

5.1: 87 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 °C

6.1: 63 percent / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C

7.1: 100 percent / PPh₃; HCO₂H; iPr₂NEt / Pd(OAc)2 / dimethylformamide / 1 h / 60 °C

8.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 0.25 h / -78 °C

9.1: 18.0 mg / K₂CO₃ / tetrahydrofuran / 0.5 h / 0 °C

10.1: 46 percent / Pd(OAc)2; PPh₃; i-Pr₂NEt / dimethylsulfoxide / 1.5 h / 80 °C

11.1: 81 percent / NaOiPr / propan-2-ol / 1 h / 20 °C

12.1: CF₃CO₂H / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 7.1 mg / Li₂CO₃ / dimethylformamide / 14 h / 40 °C

14.1: 48 percent / PPh₃; K₂CO₃; Bu₄NCl / Pd(OAc)2 / dimethylformamide / 0.5 h / 70 °C

15.1: 47 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0 °C

16.1: 96 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C

With hydrogenchloride; manganese(IV) oxide; palladium diacetate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; formic acid; oxalyl dichloride; tetrabutyl-ammonium chloride; sodium isopropylate; lithium carbonate; potassium hexamethylsilazane; sodium naphthalenide; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; p-benzoquinone; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 5.1: Swern oxidation / 10.1: intramolecular Heck reaction / 14.1: intramolecular Heck reaction;

DOI:10.1021/ja029382u

upstream raw materials:

strychnidin-10-one

9,10-seco-strychnidin-10-oic acid

(-)-(21E)-12,13-didehydro-24-(tert-butyldimethylsilyl)-12,24-secostrychnidin-10-one

N-(2-bromophenyl)-4-methylbenzenesulfonamide

Downstream raw materials:

strychnidin-10-one

Refernces

• 1、 Nakanishi, Masato,Mori, Miwako. "Total synthesis of (-)-strychnine". . p. 1934 - 1936. Retrieved 2007/10/03.
• 2、 Cai,Hattori,Namba. "Processing of nux vomica. II. Changes in alkaloid composition of the seeds of Strychnos nux-vomica on traditional drug-processing". . p. 1295 - 1298. Retrieved 2007/10/02.