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

Description

Actinidine, also known as 6,7-dihydrocyclopenta[c]pyridine, is a member of the cyclopentapyridine class of compounds. It is characterized by the presence of two methyl substituents at positions 4 and 7, which contribute to its unique chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
Actinidine is used as a pharmaceutical compound for its potential therapeutic effects. Its unique chemical structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs and therapies.
Used in Chemical Research:
Actinidine is also utilized in chemical research as a starting material or intermediate for the synthesis of other complex organic compounds. Its distinct structure and reactivity make it a valuable tool for exploring new chemical reactions and developing novel molecules with specific properties.
Used in Material Science:
Actinidine's unique chemical properties may also find applications in material science, where it could be used to develop new materials with specific characteristics, such as improved stability, reactivity, or selectivity in various chemical processes.

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

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.