(-)-Montanine

Base Information

• Chemical Name: (-)-Montanine
• CAS No.: 642-52-4
• Molecular Formula: C17H19 N O4
• Molecular Weight: 301.34
• DSSTox Substance ID: DTXSID801107687
• Nikkaji Number: J34.197E
• Wikidata: Q105166325
• ChEMBL ID: CHEMBL1221863
• Mol file: 642-52-4.mol

Synonyms:(-)-Montanine;642-52-4;Pancracine, O2-methyl-;Compound NP-016462;Montanine (C17 alkaloid);SCHEMBL812255;CHEMBL1221863;DTXSID801107687;BDBM50190649;AKOS040738613;(1S,13S,15S,16S)-16-methoxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.013,18]nonadeca-2,4(8),9,17-tetraen-15-ol;(6R,6aS,8S,9S,11S)-5,6a,7,8,9,11-Hexahydro-9-methoxy-6,11-methano-6H-benzo[b]-1,3-benzodioxolo[5,6-e]azepin-8-ol

Chemical Property of (-)-Montanine

Chemical Property:

• PSA: 51.16000
• LogP: 1.34060
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 301.13140809
• Heavy Atom Count: 22
• Complexity: 495

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C=C2C(CC1O)N3CC2C4=CC5=C(C=C4C3)OCO5
• Isomeric SMILES: CO[C@H]1C=C2[C@H](C[C@@H]1O)N3C[C@H]2C4=CC5=C(C=C4C3)OCO5

Technology Process of (-)-Montanine

There total 94 articles about (-)-Montanine 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: 87.0%

(+/-)-O-benzylcoccinine (139025-49-3,144609-93-8) → (+/-)-coccinine (485-57-4,642-52-4,43208-82-8,98632-48-5,139068-98-7,139068-99-8)

Guidance literature:

With trimethylsilyl iodide; In chloroform;

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

Reference yield: 86.7%

(+/-)-O-benzylcoccinine (139025-49-3,144609-93-8) → (+/-)-coccinine (485-57-4,642-52-4,43208-82-8,98632-48-5,139068-98-7,139068-99-8)

Guidance literature:

With trimethylsilyl iodide; In chloroform; for 5h; Ambient temperature;

DOI:10.1021/jo00052a051

Reference yield: 51.0%

C18H21NO5 (191787-73-2) → (-)-montanine (642-52-4) + (-)-coccinine (485-57-4)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at 0 - 30 ℃; for 19h; enantioselective reaction;

DOI:10.1002/anie.201307324

upstream raw materials:

C₂₂H₂₉NO₆Si

C₂₂H₃₁NO₄Si

C₁₇H₁₇NO₄*ClH

C₁₈H₁₉NO₅

Downstream raw materials:

pancracine

(-)-manthine

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, Miyuki,Hoshino, Osamu,Iitaka, Yoichi. "A FIRST TOTAL SYNTHESIS OF MONTANINE-TYPE AMARYLLIDACEAE ALKALOIDS, (+/-)-COCCININE, (+/-)-MONTANINE, AND (+/-)-PANCRACINE". . p. 7079 - 7082. Retrieved 2007/10/02.