Aspidodasycarpine

Base Information

• Chemical Name: Aspidodasycarpine
• CAS No.: 2744-47-0
• Molecular Formula: C₂₁H₂₆N₂O₄
• Molecular Weight: 370.448
• DSSTox Substance ID: DTXSID10693260
• Mol file: 2744-47-0.mol

Synonyms:aspidodasycarpine

Chemical Property of Aspidodasycarpine

Chemical Property:

• Vapor Pressure: 4.08E-13mmHg at 25°C
• Boiling Point: 554.2°C at 760 mmHg
• Flash Point: 289°C
• PSA: 79.82000
• Density: 1.33g/cm³
• LogP: 2.02300
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 370.18925731
• Heavy Atom Count: 27
• Complexity: 681

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CNC2CC1C(C34C2(NC5=CC=CC=C53)OCC4)(CO)C(=O)OC
• Isomeric SMILES: C/C=C/1\CN[C@H]2C[C@@H]1C([C@@]34[C@@]2(NC5=CC=CC=C53)OCC4)(CO)C(=O)OC

Technology Process of Aspidodasycarpine

There total 17 articles about Aspidodasycarpine 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: 76.0%

C28H32N2O6S → aspidodasycarpine (2744-47-0,26988-11-4)

Guidance literature:

With naphthalene radical anion sodium salt; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1021/jacs.6b00764

Reference yield:

C29H25N3O7S2 → aspidodasycarpine (2744-47-0,26988-11-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: sodium tetrahydroborate / methanol; dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 22 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / cyclohexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

4.1: sodium carbonate / methanol; dichloromethane; water / 3 h / 22 °C / Inert atmosphere

5.1: trifluorormethanesulfonic acid / 1,4-dioxane / 2 h / 22 °C / Inert atmosphere; Molecular sieve

6.1: sodium tetrahydroborate / methanol; dichloromethane / 0.17 h / 22 °C / Inert atmosphere

6.2: 2 h / 0 °C / Inert atmosphere

7.1: sodium hydrogencarbonate; N-iodo-succinimide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: lithium tert-butoxide / dimethyl sulfoxide / 1 h / 120 °C / Microwave irradiation; Inert atmosphere

9.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 5 h / 22 °C / Inert atmosphere

9.2: 48 h / 22 °C / Inert atmosphere

10.1: sodium tetrahydroborate / methanol / 2 h / 0 °C / Inert atmosphere

11.1: 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; sodium chlorite; 2-methyl-but-2-ene / dichloromethane / 10 h / 22 °C / pH 4 / Inert atmosphere

12.1: methanol; hexane / 0.17 h / 0 °C / Inert atmosphere

13.1: boron tribromide / dichloromethane / 1 h / -78 °C / Inert atmosphere

14.1: naphthalene radical anion sodium salt / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

With sodium chlorite; sodium tetrahydroborate; N-iodo-succinimide; 2-methyl-but-2-ene; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; naphthalene radical anion sodium salt; boron tribromide; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; lithium tert-butoxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; cyclohexane; water; dimethyl sulfoxide; 4.1: |Aldol Condensation;

DOI:10.1021/jacs.6b00764

Reference yield:

C29H27N3O7S2 → aspidodasycarpine (2744-47-0,26988-11-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 22 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / cyclohexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

3.1: sodium carbonate / methanol; dichloromethane; water / 3 h / 22 °C / Inert atmosphere

4.1: trifluorormethanesulfonic acid / 1,4-dioxane / 2 h / 22 °C / Inert atmosphere; Molecular sieve

5.1: sodium tetrahydroborate / methanol; dichloromethane / 0.17 h / 22 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; N-iodo-succinimide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: lithium tert-butoxide / dimethyl sulfoxide / 1 h / 120 °C / Microwave irradiation; Inert atmosphere

8.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 5 h / 22 °C / Inert atmosphere

8.2: 48 h / 22 °C / Inert atmosphere

9.1: sodium tetrahydroborate / methanol / 2 h / 0 °C / Inert atmosphere

10.1: 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; sodium chlorite; 2-methyl-but-2-ene / dichloromethane / 10 h / 22 °C / pH 4 / Inert atmosphere

11.1: methanol; hexane / 0.17 h / 0 °C / Inert atmosphere

12.1: boron tribromide / dichloromethane / 1 h / -78 °C / Inert atmosphere

13.1: naphthalene radical anion sodium salt / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

With sodium chlorite; sodium tetrahydroborate; N-iodo-succinimide; 2-methyl-but-2-ene; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; naphthalene radical anion sodium salt; boron tribromide; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; lithium tert-butoxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; cyclohexane; water; dimethyl sulfoxide; 3.1: |Aldol Condensation;

DOI:10.1021/jacs.6b00764

Downstream raw materials:

N-methylaspidodasycarpine

Desformo-aspidodasycarpin

Refernces