(-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol

Base Information

• Chemical Name: (-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol
• CAS No.: 14019-10-4
• Molecular Formula: C21H29NO
• Molecular Weight: 311.46106
• UNII: QZH7WR4VKJ
• DSSTox Substance ID: DTXSID70161253
• Wikidata: Q27287577
• ChEMBL ID: CHEMBL1325
• Mol file: 14019-10-4.mol

Synonyms:(3S,6S)-Methadol;(-)-alpha-Methadol;14019-10-4;QZH7WR4VKJ;UNII-QZH7WR4VKJ;(-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol;CHEMBL1325;Benzeneethanol, beta-(2-(dimethylamino)propyl)-alphaa-ethyl-beta-phenyl-, acetate (ester), (-)-;NCGC00247678-01;1-alpha-Methadol;LEVOMETHADYL [VANDF];LEVOMETHADYL [WHO-DD];(-)-.ALPHA.-METHADOL;DTXSID70161253;BDBM50223634;Q27287577

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Chemical Property of (-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol

Chemical Property:

• Boiling Point: 437.0±45.0 °C(Predicted)
• PKA: 14.56±0.20(Predicted)
• PSA: 23.47000
• Density: 1.013±0.06 g/cm3(Predicted)
• LogP: 4.08380
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 311.224914549
• Heavy Atom Count: 23
• Complexity: 311

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O
• Isomeric SMILES: CC[C@@H](C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O
• Uses: The enatiomer of (+)-α-Methadol (M225860) and is more effective in binding to opiate receptors. The relative activities of (-)-α-Methadol and (+)-α-Methadol are reversed upon acetylation. A metabolite of (-)-α-Acetylmethadol (A186325).

Technology Process of (-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol

There total 11 articles about (-)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol 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: 100.0%

(+)-Methadone hydrochloride (15284-15-8) → (3S,6S)-Methadol (14019-10-4)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In ethanol; at 20 ℃; for 3h;

DOI:10.1016/S0957-4166(03)00019-3

Reference yield:

→ (+/-)-alpha-methadol (545-90-4,14019-10-4,15529-92-7,17199-54-1,17199-55-2,63869-11-4,86360-60-3)

Guidance literature:

With methanol; platinum; Hydrogenation;

DOI:10.1021/jo01161a023

Reference yield:

→ (3S,6S)-Methadol (14019-10-4)

Guidance literature:

With water; platinum; Hydrogenation;

DOI:10.1021/ja01170a025

upstream raw materials:

(+)-Methadone hydrochloride

Diphenylacetonitrile

(S)-(+)-2,2-diphenyl-4-dimethylaminopentanenitrile

formaldehyd

Downstream raw materials:

levomethadyl acetate hydrochloride

(+/-)-erythro-5-acetoxy-2-dimethylamino-4,4-diphenyl-heptane

Refernces

• 1、 Carroll,Brine,Chen,Kohl,Welch. "Synthesis of (-) α acetylmethadol metabolites and related compounds". . p. 3521 - 3524. Retrieved 2007/10/06.