Cavidine

Base Information

• Chemical Name: Cavidine
• CAS No.: 32728-75-9
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.418
• Mol file: 32728-75-9.mol

Synonyms:12H-Benzo[a]-1,3-benzodioxolo[4,5-g]quinolizine,6,6a,11,14-tetrahydro-8,9-dimethoxy-6-methyl-, (6S-trans)-;(+)-Cavidine;Cavidin;Cavidine;

Chemical Property of Cavidine

Chemical Property:

• Vapor Pressure: 8.96E-09mmHg at 25°C
• Refractive Index: 1.643
• Boiling Point: 463.6 °C at 760 mmHg
• PKA: 6.57±0.40(Predicted)
• Flash Point: 133.8 °C
• PSA: 40.16000
• Density: 1.3 g/cm³
• LogP: 3.58690

Purity/Quality:

98%Min ^*data from raw suppliers

Cavidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Cavidine is a benzylisoquinoline alkaloid biosynthesized stereospecifically from (R)-(–)-reticuline in *Corydalis meifolia* Wall., demonstrating its role as a key intermediate in the plant's alkaloid pathway.

Technology Process of Cavidine

There total 13 articles about Cavidine 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: 96.0%

C21H21NO4 → cavidine (32728-75-9)

Guidance literature:

With platinum(IV) oxide; hydrogen; acetic acid; for 12h; under 760.051 Torr;

DOI:10.1021/acs.orglett.7b00414

Reference yield:

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1745-07-9) → cavidine (32728-75-9)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(l) iodide; benzoic acid; (R,S_a)-N-PINAP / toluene / 12 h / 40 °C / Schlenk technique; Inert atmosphere; Molecular sieve

2: potassium carbonate; methanol / 2 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium formate / N,N-dimethyl-formamide; water / 2 h / 100 °C / Inert atmosphere

4: acetic acid; platinum(IV) oxide; hydrogen / 12 h / 760.05 Torr

With methanol; platinum(IV) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (R,S_a)-N-PINAP; hydrogen; sodium formate; potassium carbonate; acetic acid; benzoic acid; In water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.orglett.7b00414

Reference yield:

5-bromo-benzo[1,3]dioxole-4-carbaldehyde (72744-54-8) → cavidine (32728-75-9)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(l) iodide; benzoic acid; (R,S_a)-N-PINAP / toluene / 12 h / 40 °C / Schlenk technique; Inert atmosphere; Molecular sieve

2: potassium carbonate; methanol / 2 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium formate / N,N-dimethyl-formamide; water / 2 h / 100 °C / Inert atmosphere

4: acetic acid; platinum(IV) oxide; hydrogen / 12 h / 760.05 Torr

With methanol; platinum(IV) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (R,S_a)-N-PINAP; hydrogen; sodium formate; potassium carbonate; acetic acid; benzoic acid; In water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.orglett.7b00414

upstream raw materials:

N-benzoyl-norreticuline

reticuline

(R)-reticuline

Methanesulfonic acid (6S,6aR)-8,9-dimethoxy-6,11,12,14-tetrahydro-6aH-[1,3]dioxolo[4,5-h]isoquino[2,1-b]isoquinolin-6-ylmethyl ester

Refernces

THE BIOSYNTHESIS OF THE ALKALOIDS OF CORYDALIS MEIFOLIA WALL.

10.1016/S0040-4020(01)87469-X

The study investigates the biosynthesis of alkaloids in Corydalis meifolia Wall., a plant used in traditional medicine. The researchers used tracer experiments to demonstrate that the alkaloids corlumine, cavidine, and yenshusomine are stereospecifically biosynthesized from (R)-(?)-reticuline. They fed various labeled precursors, including tyrosine, norreticuline, and reticuline, to young branches of the plant and observed the incorporation of these precursors into the target alkaloids. The results showed that certain precursors, like norreticuline and reticuline, were efficiently metabolized into the alkaloids, while others were not. The study also established the regiospecificity of the biosynthetic pathway by tracking the labeled atoms through various chemical transformations, confirming that reticuline is a true precursor of these alkaloids. The findings provide valuable insights into the biogenetic pathway of these medically relevant compounds.