cis-Syn-cis-dicyclohexano-18-crown-6

Base Information

• Chemical Name: cis-Syn-cis-dicyclohexano-18-crown-6
• CAS No.: 15128-65-1
• Molecular Formula: C20H36O6
• Molecular Weight: 372.5
• UNII: 6ZD3SD8ZPM
• Nikkaji Number: J642.794D
• Mol file: 15128-65-1.mol

Synonyms:6ZD3SD8ZPM;cis-syn-cis-dicyclohexano-18-crown-6;Dicyclohexyl-18-crown-6, isomer A;cis-syn-cis-dicyclohexyl-18-crown-6;cis-2,5,8,15,18,21-Hexaoxatricyclo(20.4.0.09,14)hexacosane;2,3,11,12-Dicyclohexano-1,4,7,10,13,16-hexaoxacyclooctadecane, cis-;Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecin, eicosahydro-, meso-;15128-65-1;Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecin, eicosahydro-, (4ar*,11as*,15ar*,22as*)-;Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecin, eicosahydro-, (4aR,11aS,15aR,22aS)-rel-;UNII-6ZD3SD8ZPM

Chemical Property of cis-Syn-cis-dicyclohexano-18-crown-6

Chemical Property:

• Melting Point: 59 - 61 °C
• PSA: 55.38000
• LogP: 2.72200
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 372.25118886
• Heavy Atom Count: 26
• Complexity: 300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC2C(C1)OCCOCCOC3CCCCC3OCCOCCO2
• Isomeric SMILES: C1CC[C@H]2[C@@H](C1)OCCOCCO[C@H]3CCCC[C@H]3OCCOCCO2

Technology Process of cis-Syn-cis-dicyclohexano-18-crown-6

There total 3 articles about cis-Syn-cis-dicyclohexano-18-crown-6 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: 38.0%

C16H30O5 (54356-45-5,54383-25-4,74310-49-9) + diethylene glycol ditosylate (7460-82-4) → (R)-trans-anti-trans-dicyclohexano-18-crown-6 (15128-65-1,15128-66-2,16069-36-6,54383-26-5,54383-27-6,62623-98-7,88904-37-4)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 20 ℃; for 40h;

DOI:10.1016/S0040-4039(02)01187-5

Reference yield:

C30H42O5 → (R)-trans-anti-trans-dicyclohexano-18-crown-6 (15128-65-1,15128-66-2,16069-36-6,54383-26-5,54383-27-6,62623-98-7,88904-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂; acetic acid / 10 percent Pd-C / methanol / 3620.04 Torr

2: 38 percent / NaH / dimethylsulfoxide / 40 h / 20 °C

With hydrogen; sodium hydride; acetic acid; palladium on activated charcoal; In methanol; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(02)01187-5

Reference yield:

→ (R)-trans-anti-trans-dicyclohexano-18-crown-6 (15128-65-1,15128-66-2,16069-36-6,54383-26-5,54383-27-6,62623-98-7,88904-37-4)

Guidance literature:

aus (+-)-Diol (8a), Ditosylat (9);

upstream raw materials:

C₁₆H₃₀O₅

diethylene glycol ditosylate

Downstream raw materials:

2,2'-(((1R,2S)-cyclohexane-1,2-diyl)bis(oxy))bis(ethan-1-ol)

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