CYCLIZIDINE

Base Information

• Chemical Name: CYCLIZIDINE
• CAS No.: 84393-28-2
• Molecular Formula: C17H25NO3
• Molecular Weight: 291.388
• Mol file: 84393-28-2.mol

Synonyms:(1aR,4S,5S,6S,6aR,6bS)-4-((1E,3E)-4-Cyclopropyl-2-methyl-buta-1,3-dienyl)-6-methyl-octahydro-1-oxa-3a-aza-cyclopropa[e]indene-5,6-diol;

Chemical Property of CYCLIZIDINE

Chemical Property:

• Melting Point: 184 °C (diethyl ether)
• PSA: 56.23000
• LogP: 1.17260

Purity/Quality:

CYCLIZIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of CYCLIZIDINE

There total 24 articles about CYCLIZIDINE 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: 79.0%

C25H33NO4 (1267652-04-9) → cyclizidine (84393-28-2)

Guidance literature:

With 4,4'-di-tert-butylbiphenyl; lithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol103094j

Reference yield:

(R)-4-((R)-1-hydroxy-1-methylprop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (870137-18-1) → cyclizidine (84393-28-2)

Guidance literature:

Multi-step reaction with 21 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; methanesulfonamide / water; tert-butyl alcohol / 24 h / 20 °C

3.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 12 h / 50 °C / Inert atmosphere

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

7.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

8.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

9.2: 0 - 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

11.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 50 °C / Inert atmosphere

12.1: propan-1-ol; potassium hydroxide / water / 12 h / Reflux

13.1: sodium carbonate / tetrahydrofuran; water / 3 h / 0 °C

14.1: oxone; Na₂EDTA; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / 3 h / 0 °C

15.1: Dess-Martin periodane / dichloromethane / 20 °C

16.1: tetrahydrofuran / -78 - 0 °C / Inert atmosphere

17.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

18.1: piperidine / acetonitrile / 12 h / 20 °C / Inert atmosphere

19.1: bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

19.2: 0 - 20 °C / Inert atmosphere

20.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; CO₃Tl₂ / tetrahydrofuran; water / 3 h / 20 °C

21.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

With piperidine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; propan-1-ol; dmap; bis-triphenylphosphine-palladium(II) chloride; 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; oxone; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonamide; 1,1,1-trifluoro-2-propanone; 4,4'-di-tert-butylbiphenyl; CO₃Tl₂; Na₂EDTA; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; lithium; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 16.1: Grignard reaction / 20.1: Suzuki-Miyaura coupling;

DOI:10.1021/ol103094j

Reference yield:

C30H45NO6Si (1267651-79-5) → cyclizidine (84393-28-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 12 h / 50 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

5.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

6.2: 0 - 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 50 °C / Inert atmosphere

9.1: propan-1-ol; potassium hydroxide / water / 12 h / Reflux

10.1: sodium carbonate / tetrahydrofuran; water / 3 h / 0 °C

11.1: oxone; Na₂EDTA; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / 3 h / 0 °C

12.1: Dess-Martin periodane / dichloromethane / 20 °C

13.1: tetrahydrofuran / -78 - 0 °C / Inert atmosphere

14.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

15.1: piperidine / acetonitrile / 12 h / 20 °C / Inert atmosphere

16.1: bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

16.2: 0 - 20 °C / Inert atmosphere

17.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; CO₃Tl₂ / tetrahydrofuran; water / 3 h / 20 °C

18.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

With piperidine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; propan-1-ol; bis-triphenylphosphine-palladium(II) chloride; oxone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1,1-trifluoro-2-propanone; 4,4'-di-tert-butylbiphenyl; CO₃Tl₂; Na₂EDTA; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; lithium; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 13.1: Grignard reaction / 17.1: Suzuki-Miyaura coupling;

DOI:10.1021/ol103094j

upstream raw materials:

(R)-4-((R)-1-hydroxy-1-methylprop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

C₃₀H₄₅NO₆Si

C₃₈H₅₃NO₇Si

C₃₄H₄₃NO₆Si

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