(1S,4S,7S,8S,11S,12R,13S)-2,12-Dimethyl-13-propan-2-yl-10-oxa-2-azatetracyclo[5.4.1.18,11.04,12]tridecan-9-one

Base Information

• Chemical Name: (1S,4S,7S,8S,11S,12R,13S)-2,12-Dimethyl-13-propan-2-yl-10-oxa-2-azatetracyclo[5.4.1.18,11.04,12]tridecan-9-one
• CAS No.: 2115-91-5
• Molecular Formula: C₁₆H₂₅NO₂
• Molecular Weight: 263.38
• Hs Code.: 29399990
• DSSTox Substance ID: DTXSID70896917
• Wikipedia: Dendrobine
• Wikidata: Q76149937

Synonyms:dendrobine;dendrobine hydrochloride

Chemical Property of (1S,4S,7S,8S,11S,12R,13S)-2,12-Dimethyl-13-propan-2-yl-10-oxa-2-azatetracyclo[5.4.1.18,11.04,12]tridecan-9-one

Chemical Property:

• Vapor Pressure: 8.25E-06mmHg at 25°C
• Melting Point: 135-136℃
• Refractive Index: 1.525
• Boiling Point: 374.602 °C at 760 mmHg
• PKA: 9.49±0.60(Predicted)
• Flash Point: 132.762 °C
• PSA: 29.54000
• Density: 1.101 g/cm³
• LogP: 2.09820
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 263.188529040
• Heavy Atom Count: 19
• Complexity: 435

Purity/Quality:

99% ^*data from raw suppliers

Dendrobine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1C2C3CCC4C3(C(C1OC2=O)N(C4)C)C
• Isomeric SMILES: CC(C)[C@H]1[C@@H]2[C@@H]3CC[C@H]4[C@@]3([C@@H]([C@H]1OC2=O)N(C4)C)C
• General Description: Dendrobine is a major alkaloid found in the Chinese orchid *Dendrobium nobile*, known for its antipyretic and hypotensive properties. It features a complex azatricyclic structure with multiple stereogenic centers, and its synthesis has been achieved through an enantioselective route involving key transformations such as a Pauson-Khand reaction and carbamyl radical cascade. dendrobine's biological activities and intricate molecular architecture make it a subject of interest in medicinal chemistry and synthetic studies.

Technology Process of (1S,4S,7S,8S,11S,12R,13S)-2,12-Dimethyl-13-propan-2-yl-10-oxa-2-azatetracyclo[5.4.1.18,11.04,12]tridecan-9-one

There total 101 articles about (1S,4S,7S,8S,11S,12R,13S)-2,12-Dimethyl-13-propan-2-yl-10-oxa-2-azatetracyclo[5.4.1.18,11.04,12]tridecan-9-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1S,4S,7S,8R,11R,12R,13S)-13-isopropyl-12-methyl-10-oxa-2-azatetracyclo<5.4.1.1.8,11.04,12>tridecan-9-one (6846-34-0) → dendrobine (2115-91-5,30646-45-8,57760-63-1,62624-23-1,27150-29-4,27298-09-5)

Guidance literature:

With formic acid; In water; for 12h; Reflux;

DOI:10.1021/acs.orglett.8b01782

Reference yield: 65.0%

C17H27NO3 (1375797-87-7) → dendrobine (2115-91-5,30646-45-8,57760-63-1,62624-23-1,27150-29-4,27298-09-5)

Guidance literature:

With sodium tetrahydroborate; In isopropyl alcohol; at 20 - 50 ℃; for 77h; Inert atmosphere;

DOI:10.1002/anie.201108564

Reference yield: 62.0%

methyl N-methyl-11α-methyl-7-keto-6α-(2-propyl)-2,3,4,5,6,8α,9α,10α-octahydrocyclopentenoindole-5β-carboxylate (53375-97-6,53403-50-2) → (+/-)-Dendrobin (2115-91-5,30646-45-8,57760-63-1,62624-23-1,27150-29-4,27298-09-5)

Guidance literature:

With sodium tetrahydroborate; In isopropyl alcohol; at 23 ℃; for 24h;

DOI:10.1021/ja00524a027

upstream raw materials:

formaldehyd

(1S,4S,7S,8R,11R,12R,13S)-13-isopropyl-12-methyl-10-oxa-2-azatetracyclo<5.4.1.1.^8,11.0^4,12>tridecan-9-one

(+)-trans-verbenol

(+)-(1R,2S,6R)-6-isopropyl-3-methyl-2-methylamino-cyclohex-3-enol

Refernces

A short synthesis of (-)-dendrobine

10.1021/ja990707p

The research focuses on the concise, enantioselective synthesis of (-)-dendrobine (1), a major alkaloid constituent of the Chinese ornamental orchid Dendrobium nobile, known for its antipyretic and hypotensive activities. The purpose of the study was to develop an efficient and stereoselective synthetic route to this molecule, which was achieved in 13 steps, starting from (+)-trans-verbenol (6). The synthesis involved a cascade reaction with a carbamyl radical to form amino alcohol 3, establishing the three principal stereogenic centers. Key chemicals used in the process included Pauson-Khand reaction components, such as N-propargyl derivative 8, and various reagents for functional group transformations, like iodotrimethylsilane, phenylselenenyl bromide, diethylaluminum cyanide, and sodium borohydride. The synthesis concluded with the formation of (-)-dendrobine (1) from cyanoketone 13 through a series of reactions, including reduction, Barton-McCombie deoxygenation, and epimerization, ultimately yielding the target compound with a 75% overall yield from 14 based on the recovered 15b. The study also highlighted the intriguing solvent effect on the Pauson-Khand reaction and the efficient formation of the azatricyclo[6.2.1.04,11]undecane ring system.

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