Diaboline

Base Information

• Chemical Name: Diaboline
• CAS No.: 509-40-0
• Molecular Formula: C21H24N2O3
• Molecular Weight: 352.4269
• UNII: 9ZF1MM6TXS
• Nikkaji Number: J1.844.079B
• Wikidata: Q27273423
• Mol file: 509-40-0.mol

Synonyms:1-(14-hydroxy-15-oxa-1,11-diazahexacyclo(16.3.1.04,12.04,21.05,10.013,19)docosa-5,7,9,17-tetraen-11-yl)ethanone;diaboline

Chemical Property of Diaboline

Chemical Property:

• Vapor Pressure: 1.93E-16mmHg at 25°C
• Melting Point: 187°
• Boiling Point: 624.1°Cat760mmHg
• Flash Point: 331.3°C
• PSA: 53.01000
• Density: 1.4g/cm³
• LogP: 1.66140
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 352.17869263
• Heavy Atom Count: 26
• Complexity: 678

Purity/Quality:

98%min ^*data from raw suppliers

DIABOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1C2C3C4CC5C2(CCN5CC4=CCOC3O)C6=CC=CC=C61
• Isomeric SMILES: CC(=O)N1[C@H]2[C@H]3[C@H]4C[C@H]5[C@@]2(CCN5CC4=CCO[C@H]3O)C6=CC=CC=C61

Technology Process of Diaboline

There total 23 articles about Diaboline 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:

(6R,16α,19E)-1-acetyl-19,20-didehydro-6-(ethylthio)-18-[[tris(1-methylethyl)silyl]oxy]-curan-17-ol (482351-16-6) → diaboline (509-40-0)

Guidance literature:

(6R,16α,19E)-1-acetyl-19,20-didehydro-6-(ethylthio)-18-[[tris(1-methylethyl)silyl]oxy]-curan-17-ol; With sodium tetrahydroborate; nickel dichloride; In methanol; ethanol; at 20 ℃;

With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; at 20 ℃; for 1h;

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; for 12h; Further stages.;

DOI:10.1016/j.tet.2004.06.141

Reference yield:

trimethyl-(2-nitro-phenyl)-stannane (76074-18-5) → diaboline (509-40-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 100 percent / Pd₂(dba)3*CHCl₃; Ph₃As; CuI / dimethylformamide / 48 h / 20 °C

2.1: 100 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 24 h / 20 °C

3.1: 100 percent / 3HF*Et₃N / tetrahydrofuran / 50 h / 20 °C

4.1: N,N-diisoropylethylamine / CH₂Cl₂ / 0.5 h / -78 °C

5.1: N,N-diisoropylethylamine / CH₂Cl₂ / 1 h / -78 °C

6.1: 10.0 mg / Zn; aq. NH₄Cl / methanol / 2 h / 20 °C

7.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH₂Cl₂ / 2 h / 20 °C

8.1: 68 percent / NaBH₃CN; TiCl₄ / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

9.1: HCl / methanol / 3 h / 55 °C

10.1: pyridine / 36 h / 20 °C

11.1: NaOMe / methanol / 0.5 h / 20 °C

12.1: 12.6 mg / imidazole / CH₂Cl₂; dimethylformamide / 2 h / 4 °C

13.1: NiCl₂; NaBH₄ / ethanol; methanol / 20 °C

13.2: SO₃*Py; Et₃N / dimethylsulfoxide / 1 h / 20 °C

13.3: 3.2 mg / 3HF*Et₃N / tetrahydrofuran / 12 h

With pyridine; 1H-imidazole; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; copper(l) iodide; triphenyl-arsane; 4 A molecular sieve; sodium methylate; titanium tetrachloride; sodium cyanoborohydride; ammonium chloride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; nickel dichloride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Stille coupling;

DOI:10.1016/j.tet.2004.06.141

Reference yield:

(3R)-3-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]cyclohexanone (482351-10-0) → diaboline (509-40-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 89 percent / I₂; DMAP / CH₂Cl₂ / 5 h / 20 °C

2.1: 100 percent / Pd₂(dba)3*CHCl₃; Ph₃As; CuI / dimethylformamide / 48 h / 20 °C

3.1: 100 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 24 h / 20 °C

4.1: 100 percent / 3HF*Et₃N / tetrahydrofuran / 50 h / 20 °C

5.1: N,N-diisoropylethylamine / CH₂Cl₂ / 0.5 h / -78 °C

6.1: N,N-diisoropylethylamine / CH₂Cl₂ / 1 h / -78 °C

7.1: 10.0 mg / Zn; aq. NH₄Cl / methanol / 2 h / 20 °C

8.1: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH₂Cl₂ / 2 h / 20 °C

9.1: 68 percent / NaBH₃CN; TiCl₄ / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

10.1: HCl / methanol / 3 h / 55 °C

11.1: pyridine / 36 h / 20 °C

12.1: NaOMe / methanol / 0.5 h / 20 °C

13.1: 12.6 mg / imidazole / CH₂Cl₂; dimethylformamide / 2 h / 4 °C

14.1: NiCl₂; NaBH₄ / ethanol; methanol / 20 °C

14.2: SO₃*Py; Et₃N / dimethylsulfoxide / 1 h / 20 °C

14.3: 3.2 mg / 3HF*Et₃N / tetrahydrofuran / 12 h

With pyridine; 1H-imidazole; hydrogenchloride; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; copper(l) iodide; triphenyl-arsane; 4 A molecular sieve; iodine; sodium methylate; titanium tetrachloride; sodium cyanoborohydride; ammonium chloride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; nickel dichloride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Stille coupling;

DOI:10.1016/j.tet.2004.06.141

upstream raw materials:

henningsamine, O-acetyldiaboline A

(6R,16α,19E)-1-acetyl-19,20-didehydro-6-(ethylthio)-18-[[tris(1-methylethyl)silyl]oxy]-curan-17-ol

trimethyl-(2-nitro-phenyl)-stannane

(3R)-3-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]cyclohexanone

Refernces

• 1、 Kapoor, V. K.,Sharma, S. K.,Chagti, K. K.,Singh, Manjit. "Synthesis and Hypotensive Activity of Diaboline". . p. 641 - 644. Retrieved 2007/10/02.