(+-)-Lythranidine

Base Information

• Chemical Name: (+-)-Lythranidine
• CAS No.: 70832-04-1
• Molecular Formula: C₂₆H₃₅NO₄
• Molecular Weight: 425.568
• DSSTox Substance ID: DTXSID50991090
• Nikkaji Number: J3.042.130B
• Wikipedia: Lythranidine
• Wikidata: Q6710338,Q100724244
• Mol file: 70832-04-1.mol

Synonyms:(+-)-lythranidine;lythranidine

Chemical Property of (+-)-Lythranidine

Chemical Property:

• Vapor Pressure: 2.18E-18mmHg at 25°C
• Boiling Point: 661.3°C at 760 mmHg
• Flash Point: 353.7°C
• PSA: 81.95000
• Density: 1.142g/cm³
• LogP: 4.28810
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 425.25660860
• Heavy Atom Count: 31
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C=C(CCC(CC3CCCC(N3)CC(CCC4=CC2=C(C=C4)O)O)O)C=C1
• Description: A minor alkaloid obtained from Lythrum anceps Mak., the base is a colourless oil which is non-crystallizable. It contains one methoxyl group, a phenolic and two non-phenolic hydroxyl groups and a piperidine ring. The O-acetate is identical with Lythranine (q.v.) and the O,O,O-triacetate has been obtained as colourless crystals, m.p. 180-217°C (dec.); [α]25D - 27°. Methylation with CH2N2 gives a mixture of the O-methyl ether which is amorphous and the O,N-dimethyl derivative, colourless crystals, m.p. 167 _9°C. Oxidation of the former with KMn04 yields 2: 2'-dimethoxydiphenyl-5: 5'-dicarboxylic acid. When subjected to double Hofmann degradations, each followed by hydrogenation, the alkaloid gives a nitrogen-free base, C27H3S03, m.p. 13 2.5-134°C.

Technology Process of (+-)-Lythranidine

There total 15 articles about (+-)-Lythranidine 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:

N-hydroxypiperidine (4801-58-5) → 3,11-epi-Lythranidine (17812-78-1,70832-04-1,134779-76-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1. HgO (yellow) / 1. CH₂Cl₂, 30min, 2. CHCl₃, reflux, 24h

2: 1. m-chloroperoxybenzoic acid (MCPBA) / 1. CHCl₂, r.t., 1h; 2. CHCl₃, reflux, 40h

3: 74 percent / Zn, ethylenediaminetetraacetic acid / acetic acid; ethanol / 0.5 h / Heating

4: 31 percent / triethylamine / benzene / 8 h

5: methanolic KOH

6: 96 percent / pyridine / 4-Dimethylaminopyridine (DMAP) / 24 h

7: H₂ / 5percent Pd/C / methanol; diethyl ether / 1.5 h / 760 Torr

8: K₂CO₃ / acetone / 4 h / Heating

9: 83 percent / I₂, silver trifluoroacetate / CH₂Cl₂; CHCl₃ / 3 h / Ambient temperature

10: 55 percent / bis(triphenylphosphine)nickel dichloride, Zn, triphenylphosphine / dimethylformamide / 21 h / 50 °C

11: 99 percent / K₂CO₃ / methanol / 18 h

12: 1. LiAlH₄, 2. H₂ / 2. 5percent Pd/C / 1. THF; 2. MeOH, r.t., 4h

With pyridine; potassium hydroxide; bis(triphenylphosphine)nickel(II) chloride; lithium aluminium tetrahydride; ethylenediaminetetraacetic acid; hydrogen; iodine; silver trifluoroacetate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; mercury(II) oxide; zinc; dmap; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; acetone; benzene;

Reference yield:

1-(benzyloxy)-4-(but-3-en-1-yl)benzene (134721-17-8) → 3,11-epi-Lythranidine (17812-78-1,70832-04-1,134779-76-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1. HgO (yellow) / 1. CH₂Cl₂, 30min, 2. CHCl₃, reflux, 24h

2: 1. m-chloroperoxybenzoic acid (MCPBA) / 1. CHCl₂, r.t., 1h; 2. CHCl₃, reflux, 40h

3: 74 percent / Zn, ethylenediaminetetraacetic acid / acetic acid; ethanol / 0.5 h / Heating

4: 31 percent / triethylamine / benzene / 8 h

5: methanolic KOH

6: 96 percent / pyridine / 4-Dimethylaminopyridine (DMAP) / 24 h

7: H₂ / 5percent Pd/C / methanol; diethyl ether / 1.5 h / 760 Torr

8: K₂CO₃ / acetone / 4 h / Heating

9: 83 percent / I₂, silver trifluoroacetate / CH₂Cl₂; CHCl₃ / 3 h / Ambient temperature

10: 55 percent / bis(triphenylphosphine)nickel dichloride, Zn, triphenylphosphine / dimethylformamide / 21 h / 50 °C

11: 99 percent / K₂CO₃ / methanol / 18 h

12: 1. LiAlH₄, 2. H₂ / 2. 5percent Pd/C / 1. THF; 2. MeOH, r.t., 4h

With pyridine; potassium hydroxide; bis(triphenylphosphine)nickel(II) chloride; lithium aluminium tetrahydride; ethylenediaminetetraacetic acid; hydrogen; iodine; silver trifluoroacetate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; mercury(II) oxide; zinc; dmap; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; acetone; benzene;

Reference yield:

trans-8-<2-(p-Benzyloxyphenyl)ethyl>-9-oxa-1-azabicyclo<4.3.0>nonane (134721-10-1) → 3,11-epi-Lythranidine (17812-78-1,70832-04-1,134779-76-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1. m-chloroperoxybenzoic acid (MCPBA) / 1. CHCl₂, r.t., 1h; 2. CHCl₃, reflux, 40h

2: 74 percent / Zn, ethylenediaminetetraacetic acid / acetic acid; ethanol / 0.5 h / Heating

3: 31 percent / triethylamine / benzene / 8 h

4: methanolic KOH

5: 96 percent / pyridine / 4-Dimethylaminopyridine (DMAP) / 24 h

6: H₂ / 5percent Pd/C / methanol; diethyl ether / 1.5 h / 760 Torr

7: K₂CO₃ / acetone / 4 h / Heating

8: 83 percent / I₂, silver trifluoroacetate / CH₂Cl₂; CHCl₃ / 3 h / Ambient temperature

9: 55 percent / bis(triphenylphosphine)nickel dichloride, Zn, triphenylphosphine / dimethylformamide / 21 h / 50 °C

10: 99 percent / K₂CO₃ / methanol / 18 h

11: 1. LiAlH₄, 2. H₂ / 2. 5percent Pd/C / 1. THF; 2. MeOH, r.t., 4h

With pyridine; potassium hydroxide; bis(triphenylphosphine)nickel(II) chloride; lithium aluminium tetrahydride; ethylenediaminetetraacetic acid; hydrogen; iodine; silver trifluoroacetate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; dmap; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; acetone; benzene;

upstream raw materials:

C₃₄H₄₁NO₅

N-hydroxypiperidine

1-(benzyloxy)-4-(but-3-en-1-yl)benzene

trans-8-<2-(p-Benzyloxyphenyl)ethyl>-9-oxa-1-azabicyclo<4.3.0>nonane