38691-95-1

Basic information

• Product Name: Tetrahydricheilanthifolinium
• Synonyms: 11,12-Dihydro-8-methoxy-9-hydroxybenzo[a]-1,3-benzodioxolo[4,5-g]quinolizinium;11,12-Dihydro-9-hydroxy-8-methoxybenzo[a]-1,3-benzodioxolo[4,5-g]quinolizinium;Groenlandicine;Tetrahydricheilanthifolinium;Tetrahydrocheilanthifoline;Tetradehydrocheilanthifoline;Dehydrocheilanthifoline;Tetradehydrocheilanthiofolinium
• CAS NO: 38691-95-1
• Molecular Formula: C19H16NO4+
• Molecular Weight: 322.33464
• Product Categories: Alkaloids
• Mol File: 38691-95-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: Tetrahydricheilanthifolinium(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydricheilanthifolinium(38691-95-1)
• EPA Substance Registry System: Tetrahydricheilanthifolinium(38691-95-1)

Safety Data

• Hazardous Substances Data: 38691-95-1(Hazardous Substances Data)

Usage

General Description

Tetrahydrocheilanthifoline, also known as THC, is an alkaloid compound found in various plant species, including Stephania japonica and Rauwolfia serpentina. It has been the subject of scientific research for its potential medicinal properties, particularly its ability to act as a natural painkiller and to modulate neurotransmitter levels in the brain. THC has been studied for its potential in the treatment of addiction, anxiety, and depression. It has also been investigated for its anti-inflammatory and anti-cancer properties. Despite its potential therapeutic benefits, further research is needed to fully understand the mechanisms of action and potential side effects of THC.

InChI:InChI=1/C19H15NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,6-9H,4-5,10H2,1H3/p+1

Synthetic route

C27H25NO6 → dehydrocheilanthifoline (38691-95-1)

Conditions	Yield
Stage #1: C27H25NO6 With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 2h;	82%

C9H6ClNO2 → dehydrocheilanthifoline (38691-95-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 2.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C 3.2: 2 h / 20 °C View Scheme

7-chloro-[1,3]dioxolo[4,5-h]isoquinoline → dehydrocheilanthifoline (38691-95-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C 2.2: 2 h / 20 °C View Scheme

C10H8ClNO2 → dehydrocheilanthifoline (38691-95-1)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 2 h / -78 - -30 °C / Inert atmosphere 2.1: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 3.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 4.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C 4.2: 2 h / 20 °C View Scheme

UDP-glucose (133-89-1) + dehydrocheilanthifoline (38691-95-1) → C25H26NO9(1+)

Conditions	Yield
With Carthamus tinctorius UGT71AE1 In aq. buffer at 30℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;

UDP-glucose (133-89-1) + dehydrocheilanthifoline (38691-95-1) → 7,8-dihydrogroenlandicine 3-O-β-D-glucopyranoside

Conditions	Yield
With Carthamus tinctorius UGT71AE1 In dimethyl sulfoxide at 30℃; pH=7.4; Enzymatic reaction;

Relevant articles and documents

Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control

The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.