16-epi-isositsirikine

Base Information

• Chemical Name: 16-epi-isositsirikine
• CAS No.: 6519-27-3
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.449
• DSSTox Substance ID: DTXSID401317258
• Wikidata: Q27138840
• ChEMBL ID: CHEMBL3940308
• Mol file: 6519-27-3.mol

Synonyms:17,18-Secoyohimban-16-carboxylicacid, 19,20-didehydro-17-hydroxy-, methyl ester, (16R,19E)- (8CI);Corynan-16-carboxylic acid, 19,20-didehydro-17-hydroxy-, methyl ester,(16R,19E)-; Isositsirikine (7CI); (16R)-E-Isositsirikine;16(R)-E-Isositsirikine; 16R,19E-Isositsirikine; 16R-Isositsirikine; Bhimberine;Indolo[2,3-a]quinolizine-2-acetic acid,3-ethylidene-1,2,3,4,6,7,12,12b-octahydro-a-(hydroxymethyl)-, methyl ester, [2R-[2a(R*),3E,12bb]]-; NSC 282700; NSC 338932;Rhazimanine

Chemical Property of 16-epi-isositsirikine

Chemical Property:

• Vapor Pressure: 2.49E-13mmHg at 25°C
• Melting Point: 263.5℃
• Boiling Point: 558.9°C at 760 mmHg
• PKA: 14.29±0.10(Predicted)
• Flash Point: 291.8°C
• PSA: 65.56000
• Density: 1.26g/cm³
• LogP: 2.75270
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 354.19434270
• Heavy Atom Count: 26
• Complexity: 564

Purity/Quality:

99% ^*data from raw suppliers

(16R)-E-Isositsirikine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2CCC3=C(C2CC1C(CO)C(=O)OC)NC4=CC=CC=C34
• Isomeric SMILES: C/C=C\1/CN2CCC3=C([C@@H]2C[C@@H]1[C@H](CO)C(=O)OC)NC4=CC=CC=C34
• Description: An amorphous alkaloid found in Vinca rosea L., this laevorotatory base has [α]25D - 20° (CHCI3). In EtOH, the ultraviolet spectrum has absorption maxima at 224, 283 and 291 m/J.. The alkaloid forms a hemisulphate, m.p. 263.5°C and an amorphous O-acetate. The picrate is obtained in the form of brilliant yellow needles when crystallized from MeOH, m.p. 216°C.

Technology Process of 16-epi-isositsirikine

There total 31 articles about 16-epi-isositsirikine 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: 86.0%

(+/-)-3-isogeissoschizine (118577-70-1) → 16,17-dihydro-3-isogeissoschizine (6519-27-3,60031-91-6,60802-15-5,70354-79-9,80287-16-7,80287-17-8,102043-86-7,115586-68-0,115586-69-1,117707-01-4,117707-02-5,118628-40-3,118628-43-6,119618-47-2,121123-59-9,121123-60-2,125993-77-3,125994-95-8)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In methanol; at 0 ℃;

DOI:10.1021/jo00266a032

Reference yield: 40.0%

(Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate (439-66-7) → 16R-E-isositsirikine (6519-27-3,60031-91-6,60802-15-5,70354-79-9,80287-16-7,80287-17-8,102043-86-7,115586-68-0,115586-69-1,117707-01-4,117707-02-5,118628-40-3,118628-43-6,119618-47-2,121123-59-9,121123-60-2,125993-77-3,125994-95-8) + 16-epi E isositsirikine (60031-91-6)

Guidance literature:

With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/acs.orglett.7b00983

Reference yield:

tryptamine (61-54-1) → (+/-)-(19Z)-Isositsirikine (6519-27-3,60031-91-6,60802-15-5,70354-79-9,80287-16-7,80287-17-8,102043-86-7,115586-68-0,115586-69-1,117707-01-4,117707-02-5,118628-40-3,118628-43-6,119618-47-2,121123-59-9,121123-60-2,125993-77-3,125994-95-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / ethanol / 28 h / Ambient temperature

2: 77 percent / trifluoroacetic acid / CH₂Cl₂ / 0.33 h / 0 °C

3: 99 percent / ethyl acetate / 0.5 h / Heating

5: 85 percent / Ba(OH)2*8H₂O / aq. ethanol / 3.5 h / Heating

6: 78 percent / 2,6-di-tert-butylpyridine, trimethyloxonium tetrafluoroborate / CH₂Cl₂ / 3 h / Ambient temperature

7: 100 percent / camphorsulphonic acid / methanol; H₂O / 24 h / 50 °C

8: 2.) NaBH₄

With barium dihydroxide; sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; camphor-10-sulfonic acid; trimethoxonium tetrafluoroborate; trifluoroacetic acid; In methanol; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/ja00183a046

upstream raw materials:

4,21-dehydrogeissoschizine hydrochloride

16R-19,20-E-Isositsirikine acetate

20E-[3S^*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine

(Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate

Refernces

• 1、 Tatsis, Evangelos C.,Carqueijeiro, Inês,Dugé De Bernonville, Thomas,Franke, Jakob,Dang, Thu-Thuy T.,Oudin, Audrey,Lanoue, Arnaud,Lafontaine, Florent,Stavrinides, Anna K.,Clastre, Marc,Courdavault, Vincent,O'Connor, Sarah E.. "A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate". . . Retrieved 2017/08/29.
• 2、 Wenkert, Ernest,Guo, Ming,Pestchanker, Mauricio J.,Shi, Yao-Jun,Vankar, Yashwant D.. "Preparation and H(3) Isomerization of C(15)-Substituted Deplancheine Derivatives. Synthesis of Geissoschizol and Geissoschizine". . p. 1166 - 1174. Retrieved 2007/10/02.