Beta-yohimbine

Catalog Number	ACM549848
CAS Number	549-84-8
Synonyms	Methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate
Molecular Weight	354.4
InChI	InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18+,19+/m0/s1
InChI Key	BLGXFZZNTVWLAY-MQPLHJKPSA-N
Purity	95%+
Complexity	555
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	5
Exact Mass	354.1943427
Heavy Atom Count	26
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	2
Isomeric SMILES	COC(=O)[C@H]1[C@@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O
Monoisotopic Mass	354.1943427
PhysicalState	Powder
Rotatable Bond Count	2
Topological Polar Surface Area	65.6 Ų

Case Study

Total Synthesis of Yohimbine Alkaloids Including β-Yohimbine

Meiyi Tang, et al. Nature Communications, 2024, 15(1), 941.

Yohimbine alkaloids exhibit a high degree of stereochemical variation in structure. Yohimbine alkaloids have a characteristic five-ring framework structure, and the representative members include yohimbine (1a), β-yohimbine (1b), pseudoyohimbine (2), astovenine (3) and venenatine (4).
Total synthesis of β-yohimbine
· By treating 8a with K2CO3 in methanol at 15 °C, olefin repositioning and C16 epimerization can be achieved, affording 15 in 80% yield.
· To a solution of compound 15 in EtOH and THF Pt/Al2O3 (5%) was then added to undergo selective olefin hydrogenation to afford compound 16.
· Compound 16 was added to the prepared DCE mixed solution of I2 and PhSiH3 at room temperature for reaction to obtain compound 20.
· A solution of 20 in THF was stirred at 0 °C under N2 atmosphere, and BH3·DMS was slowly added. After adding methanol to quench the reaction, Pd/C was added and the solution was stirred for an additional 24 hours to decompose the B-N complex. The resulting mixture was filtered, washed, evaporated under reduced pressure and purified to obtain β-yohimbine product (1b) as a colorless powder.

Custom Q&A

What is the systematic name of beta-yohimbine?

The systematic name of beta-yohimbine is methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate.

What are some other names or synonyms for beta-yohimbine?

Some other names or synonyms for beta-yohimbine are Amsonin, Amsonine, beta-Yohimbine, and β-Yohimbine.

What is the CAS number of beta-yohimbine?

The CAS number of beta-yohimbine is 549-84-8.

What is the molecular formula of beta-yohimbine?

The molecular formula of beta-yohimbine is C21H26N2O3.

What is the molecular weight of beta-yohimbine?

The molecular weight of beta-yohimbine is 354.44 g/mol.

What is the EINECS number of beta-yohimbine?

The EINECS number of beta-yohimbine is 208-977-7.

What is the chemical structure of beta-yohimbine?

The chemical structure of beta-yohimbine consists of a 17-hydroxyyohimban-16-carboxylate group.

How many nitrogen atoms are present in the molecular formula of beta-yohimbine?

There are two nitrogen atoms present in the molecular formula of beta-yohimbine.

What is the IUPAC name of beta-yohimbine?

The IUPAC name of beta-yohimbine is methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate.

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