524-03-8

Basic information

• Product Name: Actinidine
• Synonyms: Actinidine;(S)-6,7-Dihydro-4,7-dimethyl-5H-2-pyrindine
• CAS NO: 524-03-8
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.21692
• Mol File: 524-03-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 223.2°Cat760mmHg
• Flash Point: 78.3°C
• Appearance: /
• Density: 0.994g/cm³
• Vapor Pressure: 0.145mmHg at 25°C
• Refractive Index: 1.534
• PKA: 6.54±0.40(Predicted)
• CAS DataBase Reference: Actinidine(CAS DataBase Reference)
• NIST Chemistry Reference: Actinidine(524-03-8)
• EPA Substance Registry System: Actinidine(524-03-8)

Safety Data

• Hazardous Substances Data: 524-03-8(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of cyclopentapyridines that is 6,7-dihydrocyclopenta[c]pyridine bearing two methyl substituents at positions 4 and 7.

InChI:InChI=1/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1

Synthetic route

(S)-(-)-acetyltecostidine (95982-15-3) → (S)-(-)-actidine (524-03-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In acetic acid at 25℃; under 760 Torr; for 2h;	93%

(7S)-4,7-dimethyl-6,7-dihydro-5H-cyclopentapyridine-2-oxide (15524-83-1) → (S)-(-)-actidine (524-03-8)

Conditions	Yield
With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran at 25℃; for 0.5h;	80%

Actinidin (79254-93-6) → (S)-(-)-actidine (524-03-8)

Conditions	Yield
With L-(-)-O,O'-dibenzoyltartaric acid

(S)-(-)-tecostidine (34465-98-0) → (S)-(-)-actidine (524-03-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / pyridine / 48 h / 25 °C 2: 93 percent / H2 / 10percent Pd/C / acetic acid / 2 h / 25 °C / 760 Torr View Scheme

(S)-(-)-deoxyrhexifoline (131927-69-0) → (S)-(-)-actidine (524-03-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 30 percent / NaBH4 / methanol / 12 h / 0 °C 2: 70 percent / pyridine / 48 h / 25 °C 3: 93 percent / H2 / 10percent Pd/C / acetic acid / 2 h / 25 °C / 760 Torr View Scheme

7-O-thiocarbonylimidazoylcantleyine (131927-70-3) → (S)-(-)-actidine (524-03-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 78 percent / azabisisobutyronitrile, tributyltin hydride / toluene / 0.25 h / Heating 2: 30 percent / NaBH4 / methanol / 12 h / 0 °C 3: 70 percent / pyridine / 48 h / 25 °C 4: 93 percent / H2 / 10percent Pd/C / acetic acid / 2 h / 25 °C / 760 Torr View Scheme

cantleyine (23838-00-8, 30333-81-4, 143564-04-9) → (S)-(-)-actidine (524-03-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 46 percent / CH2Cl2 / 3 h / Heating 2: 78 percent / azabisisobutyronitrile, tributyltin hydride / toluene / 0.25 h / Heating 3: 30 percent / NaBH4 / methanol / 12 h / 0 °C 4: 70 percent / pyridine / 48 h / 25 °C 5: 93 percent / H2 / 10percent Pd/C / acetic acid / 2 h / 25 °C / 760 Torr View Scheme

(S)-(-)-actidine (524-03-8) → 4,7-dimethyl-6,7-dihydro-5H-[2]pyrindin-7-ol (15524-82-0)

Conditions	Yield
With potassium permanganate; water

(S)-(-)-actidine (524-03-8) → 3,7-dimethyl-3H-furo[3,4-c]pyridin-1-one (90972-10-4)

Conditions	Yield
With potassium permanganate; water

(S)-(-)-actidine (524-03-8) → (7S)-4,7-dimethyl-6,7-dihydro-5H-cyclopentapyridine-2-oxide (15524-83-1)

Conditions	Yield
With dihydrogen peroxide; acetic acid

Upstream product

• 79254-93-6 Actinidin 
• 95982-15-3 (S)-(-)-acetyltecostidine 
• 15524-83-1 (7S)-4,7-dimethyl-6,7-dihydro-5H-cyclopentapyridine-2-oxide 
• 34465-98-0 (S)-(-)-tecostidine 
• 131927-69-0 (S)-(-)-deoxyrhexifoline 
• 131927-70-3 7-O-thiocarbonylimidazoylcantleyine 
• 23838-00-8 cantleyine 

Relevant articles and documents

Stereocontrolled synthesis of the alkaloid (-)-actinidine

The alkaloid (-)-actinidine of the iridane series was synthesized using intramolecular [3+2] dipolar cycloaddition of silyl nitronates, generated from (3R/S,6S)-2,6-dimethyl-3-nitro-8-phenylthioocta-1,7E-and -1,7Z-dienes. The key nitro compounds were obtained from (-)-(S)-citronellol.