(-)-Pancracine

Base Information

• Chemical Name: (-)-Pancracine
• CAS No.: 21416-14-8
• Molecular Formula: C16H17NO4
• Molecular Weight: 287.31
• Mol file: 21416-14-8.mol

Synonyms:(6R)-(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-8t,9c-diol;Pancracin;Brunsvigin;pancracine;

Chemical Property of (-)-Pancracine

Chemical Property:

• Vapor Pressure: 2.25E-10mmHg at 25°C
• Melting Point: 272-3°C
• Boiling Point: 488.9°C at 760 mmHg
• Flash Point: 249.5°C
• PSA: 62.16000
• Density: 1.53g/cm³
• LogP: 0.68650

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This alkaloid occurs in Narcissus poeticus, Pancratium maritium and Rhodo_x0002_phiala bifida. It yields long, colourless prisms when recrystallized from MeOH and is laevorotatory with [α]25D - 74° (c 0.02, MeOH). The ultraviolet spectrum has two absorption maxima at 241 and 292 mil. It yields a crystalline perchlorate, m.p. 163-6°C and a picrate, m.p. 249-2S2°C. Two non-phenolic hydroxyl groups and one methylenedioxy group are present in the molecule. The 2-a-O-acetate is an amorphous solid which cannot be obtained crystalline but the 3-{3-0-acetate forms colourless crystals from MeOH, m.p. 213-6°C. The O,O-diacetate, also crystalline, has m.p. 163-S°C. The O-methyl derivatives occur naturally, the 2-methyl compound is Montanine (q.v.) and the 2:3-dimethyl ether is Manthine (q.v.). The structure is based primarily upon the mass spectrum fragmentation pattern.

Technology Process of (-)-Pancracine

There total 111 articles about (-)-Pancracine 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:

(-)-montanine

C₂₂H₂₉NO₆Si

C₂₂H₃₁NO₄Si

C₁₇H₁₇NO₄*ClH

Downstream raw materials:

(+/-)-brunsvigine

Refernces

• 1、 Bao, Xu,Cao, Ye-Xing,Chu, Wen-Dao,Qu, Hu,Du, Ji-Yuan,Zhao, Xian-He,Ma, Xiao-Yan,Wang, Cheng-Tao,Fan, Chun-An. "Bioinspired total synthesis of montanine-type amaryllidaceae alkaloids". . p. 14167 - 14172. Retrieved 2014/01/06.
• 2、 Ishizaki,Hoshino,Iitaka. "Total synthesis of montanine-type Amarylliidaceae alkaloids, which possess a 5,11-methanomorphanthridine ring system, through cyclization with sodium bis(2-methoxyethoxy)aluminum hydride: The first stereoselective total syntheses of (±)-montanine, (±)-coc". . p. 7285 - 7295. Retrieved 2007/10/02.