(1S,9S,13R)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol

Base Information

• Chemical Name: (1S,9S,13R)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol
• CAS No.: 39188-58-4
• Molecular Formula: C₁₉H₂₇NO
• Molecular Weight: 285.429
• DSSTox Substance ID: DTXSID201338919
• Mol file: 39188-58-4.mol

Synonyms:39188-58-4;SCHEMBL4376337;DTXSID201338919;(2S,6S,11R)-6,11-Dimethyl-3-(3-methyl-2-buten-1-yl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol

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Chemical Property of (1S,9S,13R)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol

Chemical Property:

• Melting Point: 145.4-147.2oC
• Boiling Point: 403.5°Cat760mmHg
• PKA: 10.10±0.60(Predicted)
• Flash Point: 180.8°C
• PSA: 23.47000
• Density: 1.036g/cm³
• LogP: 3.82050
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 285.209264485
• Heavy Atom Count: 21
• Complexity: 414

Purity/Quality:

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC3=C(C1(CCN2CC=C(C)C)C)C=C(C=C3)O
• Isomeric SMILES: C[C@H]1[C@@H]2CC3=C([C@]1(CCN2CC=C(C)C)C)C=C(C=C3)O

Technology Process of (1S,9S,13R)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol

There total 29 articles about (1S,9S,13R)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol 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: 94.0%

O-methyl pentazocine (577991-78-7) → pentazocin (359-83-1,7313-83-9,7361-76-4,7488-49-5,21820-34-8,39188-58-4,55643-30-6,75257-91-9,146565-86-8)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 130 ℃; for 5h;

DOI:10.1021/ja0360539

Reference yield: 86.1%

(2R,6R,11R)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol (16603-67-1) + prenyl bromide (870-63-3) → pentazocin (359-83-1,7313-83-9,7361-76-4,7488-49-5,21820-34-8,39188-58-4,55643-30-6,75257-91-9,146565-86-8)

Guidance literature:

With triethylamine; In 1-methyl-pyrrolidin-2-one; at 40 - 45 ℃; for 6h;

Reference yield:

1-methyl-7-methoxy-2-tetralone (1204-23-5) → pentazocin (359-83-1,7313-83-9,7361-76-4,7488-49-5,21820-34-8,39188-58-4,55643-30-6,75257-91-9,146565-86-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (η³-C3H5PdCl)2; (R,R)-bridged dihydroanthracene derivative ligand; Cs2CO3 / 1,2-dimethoxy-ethane / 0.25 h / 20 °C

1.2: 1,2-dimethoxy-ethane / 0.08 h / 20 °C

2.1: 98 percent / t-BuOK / tetrahydrofuran / 20 °C

3.1: 82 percent / NMO; aq. OsO₄ / tetrahydrofuran / 5 h / 20 °C

4.1: 92 percent / aq. NaIO₄ / tetrahydrofuran / 1 h / 20 °C

5.1: MgSO₄ / tetrahydrofuran; methanol / 20 °C

5.2: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 1 h

6.1: 100 percent / iPr₂NH; tetramethylenediamine; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

7.1: 94 percent / NaSEt / dimethylformamide / 5 h / 130 °C

With sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; bis(η3-allyl-μ-chloropalladium(II)); N,N,N,N,-tetramethylethylenediamine; (R,R)-bridged dihydroanthracene derivative ligand; potassium tert-butylate; magnesium sulfate; caesium carbonate; diisopropylamine; sodium thioethylate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; N,N-dimethyl-formamide; 2.1: Wittig olefination;

DOI:10.1021/ja0360539

upstream raw materials:

(-)-cis-N-Normetazocine

prenyl bromide

O-methyl pentazocine

1-methyl-7-methoxy-2-tetralone

Downstream raw materials:

Thiobenzoic acid S-[(6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester

Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester