Lochnerine

Base Information

• Chemical Name: Lochnerine
• CAS No.: 522-47-4
• Molecular Formula: C20H24 N2 O2
• Molecular Weight: 324.423
• DSSTox Substance ID: DTXSID601318507
• Wikidata: Q105361524
• ChEMBL ID: CHEMBL484153
• Mol file: 522-47-4.mol

Synonyms:Lochnerine;(+)-Lochnerine;522-47-4;Sarpagan-17-ol, 10-methoxy-;[(1S,12S,13R,14R,15E)-15-ethylidene-7-methoxy-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol;CHEMBL484153;DTXSID601318507;BDBM50480330;AKOS040744703;[(E)-ethylidene(methoxy)[?]yl]methanol;LS-88111

Chemical Property of Lochnerine

Chemical Property:

• Vapor Pressure: 5.68E-11mmHg at 25°C
• Boiling Point: 503.8°Cat760mmHg
• Flash Point: 258.5°C
• PSA: 48.49000
• Density: 1.3g/cm³
• LogP: 2.97050
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 324.183778013
• Heavy Atom Count: 24
• Complexity: 536

Purity/Quality:

98%min ^*data from raw suppliers

Lochnerine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2C3CC1C(C2CC4=C3NC5=C4C=C(C=C5)OC)CO
• Isomeric SMILES: C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@H]2CC4=C3NC5=C4C=C(C=C5)OC)CO
• Description: This carboline alkaloid has been obtained from Lochnera rosea and is also present in curare (Strychnos toxifera). Early preparations have been designated Alkaloid 'C' and C-Alkaloid T. It has [α]D + 56° (pyridine) or + n° (EtOH) and forms a crystalline picrate with a double melting point of 177-9°C and 243-5°C (dec.). The methiodide is identical with lochneram iodide, m.p. 235-8°C. A characteristic p-toluenesulphonyl derivative has been prepared, m.p. 153-4°C. One primary alcoholic hydroxyl is present and the alkaloid yields the O-acetate as colourless needles, m.p. 243°C; [α]D - 5.6° ± 3.0° (c 0.36, pyridine). The structure is that of O-methylsarpagine.

Technology Process of Lochnerine

There total 32 articles about Lochnerine 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: 90.0%

(+)-10-methoxyvellosimine (2149-40-8) → 10-methoxynormacusine B (522-47-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1002/anie.201206015

Reference yield:

4-methoxy-aniline (104-94-9) → 10-methoxynormacusine B (522-47-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: tetrahydrofuran / 20 °C

2.1: tert.-butyl lithium; 1,2-Diiodoethane / diethyl ether / -78 °C

3.1: lithium chloride; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 36 h / 100 °C / Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water

5.1: sodium sulfate / ethanol / 20 °C / Inert atmosphere

5.2: 20 °C

6.1: acetic acid / dichloromethane / 12 h / 20 °C

7.1: trifluoroacetic acid / dichloromethane / 96 h / 20 °C

8.1: sodium hydride; methanol / toluene; mineral oil / 0 °C / Inert atmosphere; Reflux

9.1: toluene; mineral oil / Inert atmosphere; Reflux; Darkness

10.1: potassium hydroxide / water; 1,4-dioxane / 48 h / Reflux

11.1: hydrogenchloride / ethanol

11.2: 12 h / 20 °C / 760.05 Torr

12.1: potassium carbonate / acetonitrile / 8 h / 20 °C / Molecular sieve; Inert atmosphere

13.1: phenol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate / tetrahydrofuran / 11 h / 75 °C

14.1: potassium tert-butylate / tetrahydrofuran; benzene

14.2: 55 °C

15.1: sodium tetrahydroborate / ethanol / 8 h / 0 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-Diiodoethane; potassium tert-butylate; tert.-butyl lithium; palladium diacetate; sodium hydride; potassium carbonate; acetic acid; sodium sulfate; trifluoroacetic acid; lithium chloride; potassium hydroxide; phenol; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; benzene; 6.1: |Pictet-Spengler Synthesis / 8.1: |Dieckmann Condensation / 9.1: |Dieckmann Condensation / 14.1: |Wittig-Horner Reaction;

DOI:10.1021/jo400469t

Reference yield:

(6S,11aS,E)-9-ethylidene-2-methoxy-6,8,9,10,11a,12-hexahydro-6,10-methanoindolo-[3,2-b]quinolizin-11(5H)-one (1428381-59-2) → 10-methoxynormacusine B (522-47-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / benzene / 1 h / 20 °C / Inert atmosphere

1.2: 12 h / 0 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / tetrahydrofuran; water / 6 h / Heating; Inert atmosphere

3.1: sodium tetrahydroborate / ethanol / 8 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; potassium tert-butylate; In tetrahydrofuran; ethanol; water; benzene; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;

DOI:10.1002/anie.201206015

upstream raw materials:

diazomethane

phenyltrimethylammonium chloride

dimethyl sulfate

(6S,11aS,E)-9-ethylidene-2-methoxy-6,8,9,10,11a,12-hexahydro-6,10-methanoindolo-[3,2-b]quinolizin-11(5H)-one

Downstream raw materials:

sarpagine

Refernces

• 1、 Banerji,Chakrabarty. "". . p. 2309. Retrieved 1974.
• 2、 Arnold et al.. "-". . p. 1505,1510. Retrieved 1958.
• 3、 Edwankar, Chitra R.,Edwankar, Rahul V.,Deschamps, Jeffrey R.,Cook, James M.. "Nature-inspired stereospecific total synthesis of P-(+)-dispegatrine and four other monomeric sarpagine indole alkaloids". . p. 11762 - 11765. Retrieved 2013/01/15.