(1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-one

Base Information

• Chemical Name: (1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-one
• CAS No.: 486-86-2
• Molecular Formula: C12H16 N2 O
• Molecular Weight: 204.272
• European Community (EC) Number: 207-643-8
• DSSTox Substance ID: DTXSID80876866
• Mol file: 486-86-2.mol

Synonyms:Caulophylline;Oprea1_623608;DTXSID80876866;486-86-2;AKOS024277848;(1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-one

Chemical Property of (1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-one

Chemical Property:

• Vapor Pressure: 1.24E-06mmHg at 25°C
• Melting Point: 137-139oC
• Refractive Index: 1.616
• Boiling Point: 400.8°Cat760mmHg
• PKA: 9.61±0.20(Predicted)
• Flash Point: 191.9°C
• PSA: 25.24000
• Density: 1.21g/cm³
• LogP: 0.83510
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 204.126263138
• Heavy Atom Count: 15
• Complexity: 359

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Methylcytisine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC2CC(C1)C3=CC=CC(=O)N3C2
• Isomeric SMILES: CN1C[C@@H]2CC(C1)C3=CC=CC(=O)N3C2
• Description: This base was first prepared synthetically by Partheil and subsequently discovered in the roots of Caulophyllurn thalictroides L. It is widespread among the Papilionaceae, being found in Baptisia australis, Genista tinctoria, Sophora microphylla, S. tetraptera, Thermopsis lanceolata and T. rhombifolia (Watt.) Richards. It is laevorotatory with [α]20D - 221 ° (H20) and furnishes the following crystalline salts and derivatives: hydrochloride, m.p. 2S0-SoC (dec.); hydriodide, m.p. 246-7°C (dec.); perchlorate, m.p. 2S4°C (dec.); aurichloride, m.p. 206°C (dec.); picrate, m.p. 230°C; picrolonate, m.p. 224-SoC (dec.) and the methiodide which occurs in two modifications, m.p. 248°C and 267-276°C.
• Uses: N-Methylcytisine (cas# 486-86-2) is a compound useful in organic synthesis.

Technology Process of (1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-one

There total 8 articles about (1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-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: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + cytisine (485-35-8) → (-)-N-methylcystine (486-86-2)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; methanol; water; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1055/s-0029-1219377

Reference yield:

(3aR,4S,8S,12R,12aS,12bR)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione → (-)-N-methylcystine (486-86-2) + N-phenyl-maleimide (941-69-5) + (3aS,4R,8S,12R,12aR,12bS)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione

Guidance literature:

In toluene; at 110 ℃; for 8h; under 760.051 Torr;

DOI:10.1016/j.tetasy.2013.09.002

Reference yield:

(3aS,4R,8S,12R,12aR,12bS)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3',4':3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione → (-)-N-methylcystine (486-86-2) + N-phenyl-maleimide (941-69-5)

Guidance literature:

In toluene; at 110 ℃; for 8h; under 760.051 Torr;

DOI:10.1016/j.tetasy.2013.09.002

upstream raw materials:

cytisine

methyl iodide

formaldehyd

Downstream raw materials:

11-methyl-8-(dimethylphenylsilyl)-7,11-diazatricyclo[7.3.1.0(2,7)]trideca-2,4-diene-6-one

N-(12-methylcytisin-3-yl)-N-phenylurea

Refernces

• 1、 Koval’skaya, Alena V.,Petrova, Polina R.,Tsypyshev, Dmitry O.,Lobov, Alexander N.,Tsypysheva, Inna P.. "Thionation of quinolizidine alkaloids and their derivatives via Lawesson’s reagent". . . Retrieved 2020.
• 2、 Niwetmarin, Worawat,Rego Campello, Hugo,Sparkes, Hazel A.,Aggarwal, Varinder K.,Gallagher, Timothy. "(-)-Cytisine: Access to a stereochemically defined and functionally flexible piperidine scaffold". supporting information. p. 5823 - 5832. Retrieved 2018/08/22.