Securitinine

Catalog Number	ACM13861717
CAS Number	13861-71-7
Synonyms	(6S,10S,11aS,11bS)-9,10,11,11a-Tetrahydro-10-methoxy-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one
Molecular Weight	247.29
InChI	InChI=1S/C14H17NO3/c1-17-11-4-5-15-10-3-2-9-6-13(16)18-14(9,8-10)12(15)7-11/h2-3,6,10-12H,4-5,7-8H2,1H3/t10-,11+,12+,14+/m1/s1
InChI Key	YKLWRYOORWTCQQ-UHXUPSOCSA-N
Purity	95%+
Complexity	470
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	4
Exact Mass	247.1208434
Heavy Atom Count	18
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	0
Isomeric SMILES	CO[C@H]1CCN2[C@@H](C1)[C@]34C[C@H]2C=CC3=CC(=O)O4
Monoisotopic Mass	247.1208434
PhysicalState	Powder
Rotatable Bond Count	1
Topological Polar Surface Area	38.8 Ų

Case Study

Total Synthesis of Various C4-Oxygenated Securinine-Type Alkaloids Including Securitinine

Park S, et al. Nature Communications, 2022, 13(1), 5149.

A strategy for the total synthesis of C4-oxygenated securinine-type alkaloids has been developed, which features stereocontrolled oxidation, rearrangement and epimerization at the N1 and C2-C4 positions of the piperidine core within the securinane scaffolds. Based on this synthetic strategy, securitinine (3) can be successfully synthesized and further used to synthesize secu'amamine D (6).
Synthesis of secu'amamine D from securitinine
· Securitinine (3) (25 mg, 0.101 mmol, 1.0 equiv.) was dissolved in 5 mL of dichloromethane and meta-Chloroperoxybenzoic acid (77%, 25 mg, 0.111 mmol, 1.1 equiv.) was added at 0 °C under argon atmosphere.
· After 10 minutes, potassium carbonate (42 mg, 0.303 mmol, 3.0 equiv.) was added at the same temperature before slowly raising to 23 °C. The reaction mixture was left for 12 hours before being quenched with brine (10 mL) and the layers were separated.
· The aqueous layer was extracted with ethyl acetate (3 x 20 mL) and the combined organic layer was dried with anhydrous sodium sulfate. The resulting filtrate was concentrated under reduced pressure. The crude residue obtained was purified by flash column chromatography to yield secu'amamine D (6) (20 mg, 75%) as a white solid.

Custom Q&A

What is the chemical name of the product Securitinine?

The chemical name of Securitinine is (6S,10S,11aS,11bS)-9,10,11,11a-Tetrahydro-10-methoxy-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one.

What are some synonyms for Securitinine?

Some synonyms for Securitinine are Securitinine and 8H-6,11b-Methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, 9,10,11,11a-tetrahydro-10-methoxy-, (6S,10S,11aS,11bS)-.

What is the CAS number of Securitinine?

The CAS number of Securitinine is 13861-71-7.

What is the molecular formula of Securitinine?

The molecular formula of Securitinine is C14H17NO3.

What is the molecular weight of Securitinine?

The molecular weight of Securitinine is 247.29.

Where is Securitinine derived from?

Securitinine is derived from the root bark of Securinega sUffructicosa grown in Formosa.

How was the structure of Securitinine established?

The structure of Securitinine was established by comparison with similar bases.

What is the reference mentioned for information about Securitinine?

The reference mentioned for information about Securitinine is Horii et aI., Chem. Pharm. Bull., 15,1633 (1967).

In what year was the structure of Securitinine established?

The structure of Securitinine was established in 1967.

What is the chemical family or class to which Securitinine belongs?

Securitinine belongs to the alkaloid class.

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