ROHITUKINE

Base Information

• Chemical Name: ROHITUKINE
• CAS No.: 71294-60-5
• Molecular Formula: C16H19NO5
• Molecular Weight: 305.331
• Mol file: 71294-60-5.mol

Synonyms:Rohitukine;(+)-cisa-5,7-dihydroxy-methyl-8-<4-(3-hydroxy-1-methyl)piperidinyl>-4H-1-benzopyran-4-one;5,7-Dihydroxy-8-[(3R,4S)-3-hydroxy-1-methyl-4-piperidinyl)-2-methyl-4H-chromen-4-one;

Chemical Property of ROHITUKINE

Chemical Property:

• Boiling Point: 494.8±45.0 °C(Predicted)
• PKA: 6.26±0.40(Predicted)
• PSA: 94.14000
• Density: 1.380±0.06 g/cm3(Predicted)
• LogP: 1.23050

Purity/Quality:

≥99% ^*data from raw suppliers

ROHITUKINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ROHITUKINE

There total 2 articles about ROHITUKINE 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:

(-)-cis-4-(3-acetyl-4,6-dimethoxy-2-hydroxy)phenyl-1-methyl-3-piperidinol (113225-14-2,113225-21-1) → (+)-cisa-5,7-dihydroxy-methyl-8-<4-(3-hydroxy-1-methyl)piperidinyl>-4H-1-benzopyran-4-one (71294-60-5,97907-01-2,106035-95-4,113300-94-0,117955-07-4,117955-10-9)

Guidance literature:

With sodium; In ethyl acetate; for 3h; Yield given; Heating;

DOI:10.1016/S0040-4020(01)90352-7

Reference yield:

cis-3-Hydroxy-4-(2,4,6-trimethoxyphenyl)-1-methylpiperidine (113225-08-4,113225-12-0,113225-18-6,113225-19-7,117955-02-9,234771-34-7) → (+)-cisa-5,7-dihydroxy-methyl-8-<4-(3-hydroxy-1-methyl)piperidinyl>-4H-1-benzopyran-4-one (71294-60-5,97907-01-2,106035-95-4,113300-94-0,117955-07-4,117955-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / boron trifluoride etherate / CH₂Cl₂ / Ambient temperature

2: sodium / ethyl acetate / 3 h / Heating

With boron trifluoride diethyl etherate; sodium; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(01)90352-7

Reference yield: 81.0%

5,7-dihydroxy-8-(3-hydroxy-1-methylpiperidin-4-yl)-2-methyl-4H-chromen-4-one (71294-60-5) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → 4-(5,7-dihydroxy-2-methyl-4-oxo-4H-chromen-8-yl)-1-methylpiperidin-3-yl 2-nitrobenzenesulfonate

Guidance literature:

5,7-dihydroxy-8-(3-hydroxy-1-methylpiperidin-4-yl)-2-methyl-4H-chromen-4-one; With pyridine; triethylamine; In dichloromethane; at 40 ℃; for 1h;

2-Nitrobenzenesulfonyl chloride; In dichloromethane; for 4h;

DOI:10.1016/j.bioorg.2021.104829

upstream raw materials:

(-)-cis-4-(3-acetyl-4,6-dimethoxy-2-hydroxy)phenyl-1-methyl-3-piperidinol

cis-3-Hydroxy-4-(2,4,6-trimethoxyphenyl)-1-methylpiperidine

Refernces