Brunsvigine

Base Information

• Chemical Name: Brunsvigine
• CAS No.: 1354-81-0
• Molecular Formula: C16H17NO4
• Molecular Weight: 287.3105
• DSSTox Substance ID: DTXSID30331596
• Nikkaji Number: J512.173F
• Wikidata: Q27105984
• Mol file: 1354-81-0.mol

Synonyms:brunsvigine

Chemical Property of Brunsvigine

Chemical Property:

• Vapor Pressure: 2.25E-10mmHg at 25°C
• Melting Point: 240°C
• Boiling Point: 488.9°Cat760mmHg
• Flash Point: 249.5°C
• PSA: 62.16000
• Density: 1.53g/cm³
• LogP: 0.68650
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 287.11575802
• Heavy Atom Count: 21
• Complexity: 481

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C=C2C1N3CC2C4=CC5=C(C=C4C3)OCO5)O)O
• Isomeric SMILES: C1[C@H]([C@H](C=C2[C@H]1N3C[C@H]2C4=CC5=C(C=C4C3)OCO5)O)O
• Description: A tetrahydroisoquinoline alkaloid, brunsvigine has been obtained from Brunsvigia cooperii. It crystallizes from H20 and colourless crystals and has the structure given above which has been confirmed by X-ray analysis.

Technology Process of Brunsvigine

There total 124 articles about Brunsvigine 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: 99.6%

(4aR*,11S*)-1,2,3,11a-tetrahydro-8,9-(methylenedioxy)-5,11-methanomorphanthridine (144609-90-5) → C16H17NO4 (1354-81-0,21416-14-8,43208-81-7,135191-24-1,144609-73-4)

Guidance literature:

With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In 1,4-dioxane; for 3h; Ambient temperature;

DOI:10.1021/jo00052a051

Reference yield: 89.5%

5,6a,7,8,9,11-hexahydro-6,11-methano[1,3]-dioxolo[4',5':4,5]benzo[1,2-e]benzo[b]azepine-8,9-diyl diacetate (21416-16-0,58023-70-4,144609-89-2,144609-91-6,144609-92-7) → (+/-)-brunsvigine (1354-81-0,21416-14-8,43208-81-7,135191-24-1,144609-73-4)

Guidance literature:

With sodium methylate; In methanol; for 0.333333h; Ambient temperature;

DOI:10.1021/jo00052a051

Reference yield: 87.0%

C16H15NO3 (139025-52-8) → (+/-)-pancracine (1354-81-0,21416-14-8,43208-81-7,135191-24-1,144609-73-4)

Guidance literature:

With sulfuric acid; In tetrahydrofuran;

DOI:10.1016/0040-4039(91)85045-7

upstream raw materials:

(1S,13S,15R,19S)-17,17-dimethyl-5,7,16,18-tetraoxa-12-azahexacyclo[10.9.1.0^2,10.0^4,8.0^13,21.O^15,19]docosa-2,4⁽⁸⁾,9,20-tetraene

C₁₆H₁₅NO₄

C₂₂H₂₉NO₆Si

C₂₅H₃₅NO₄Si

Downstream raw materials:

(+/-)-brunsvigine

(6R)-8c,9c-bis-(4-bromo-benzoyloxy)-(6at)-5,6a,7,8,9,11-hexahydro-6r,11c-methano-benzo[b][1,3]dioxolo[4',5':4,5]benzo[1,2-e]azepine

(6R)-8c,9c-dimethoxy-6-methyl-(6at)-5,6a,7,8,9,11-hexahydro-6r,11c-methano-benzo[b][1,3]dioxolo[4',5':4,5]benzo[1,2-e]azepinium; picrate

(R)-6-acetyl-8-((1Ξ,3S)-3r,4c-diacetoxy-cyclohexyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

Refernces

• 1、 Hong, An-Wei,Cheng, Tsung-Hui,Raghukumar, Vellingiri,Sha, Chin-Kang. "An expedient route to montanine-type amaryllidaceae alkaloids: Total syntheses of (-)-brunsvigine and (-)-manthine". . p. 7580 - 7585. Retrieved 2008/12/22.
• 2、 Overman,Shim. "Total synthesis of Amaryllidaceae alkaloids of the 5,11- methanomorphanthridine type. Efficient total syntheses of (-)-pancracine and (±)-pancracine". . p. 4662 - 4672. Retrieved 2007/10/02.