Cyclotriol

Base Information

• Chemical Name: Cyclotriol
• CAS No.: 135768-83-1
• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.425
• UNII: 743NA857FA
• DSSTox Substance ID: DTXSID00929146
• Wikidata: Q27896584
• Wikipedia: Cyclotriol
• Mol file: 135768-83-1.mol

Synonyms:ZK 136295;ZK-136295

Chemical Property of Cyclotriol

Chemical Property:

• Vapor Pressure: 1.22E-10mmHg at 25°C
• Boiling Point: 495.6°C at 760 mmHg
• Flash Point: 231°C
• PSA: 60.69000
• Density: 1.31g/cm³
• LogP: 3.11420
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 314.18819469
• Heavy Atom Count: 23
• Complexity: 521

Purity/Quality:

99% ^*data from raw suppliers

CYCLOTRIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C14CCC2(C(C4)O)O)CCC5=C3C=CC(=C5)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@]14CC[C@@]2([C@@H](C4)O)O)CCC5=C3C=CC(=C5)O

Technology Process of Cyclotriol

There total 17 articles about Cyclotriol 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: 100.0%

14,17α-ethanoestra-1,3,5(10)-trien-3,16α,17β-triyl triacetate (135791-00-3) → Cyclotriol (135768-83-1)

Guidance literature:

With sodium hydroxide; In methanol; at 60 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)80653-0

Reference yield:

17β-acetoxy-3-methoxy-14,17α-ethenooestra-1,3,5(10)-triene-16α-carbaldahyde (130535-89-6) → Cyclotriol (135768-83-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 74 percent / LAH / tetrahydrofuran / 0.33 h / 20 °C

2: 85 percent / pyridine / 0 dg C, 15 min, 7 deg C, 37 h

3: 100 percent / 1M KOH / methanol / 1 h / 20 °C

4: 91 percent / MeLi, CuI, HMPA, DIBAH / tetrahydrofuran; hexane / 1 h / -78 °C

5: 1.) O₃; 2.) PPh₃ / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 50 min; 2.) -78 deg C, 15 min, r.t., 30 min

6: 70.8 percent / TiCl₄, Zn / tetrahydrofuran / 1 h / 0 °C

7: 95.5 percent / NaI / 0.33 h / Ambient temperature

8: trimethylsilyl chloride, NaI / 1.5 h / Heating

9: 73 percent / NaI / 0.33 h / Ambient temperature

10: 100 percent / 1M NaOH / methanol / 2.5 h / 60 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; methyllithium; titanium tetrachloride; diisobutylaluminium hydride; ozone; triphenylphosphine; sodium iodide; zinc; In tetrahydrofuran; methanol; hexane;

DOI:10.1016/S0040-4020(01)80653-0

Reference yield:

17β-acetoxy-3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-16α-carbaldehyde (130535-91-0) → Cyclotriol (135768-83-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

2: 54 percent / pyridine / 40 h / 7 °C

3: 100 percent / 1M KOH / methanol / 20 deg C, 16 h, 50 deg C, 3 h

4: 1.) O₃; 2.) PPh₃ / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 50 min; 2.) -78 deg C, 15 min, r.t., 30 min

5: 70.8 percent / TiCl₄, Zn / tetrahydrofuran / 1 h / 0 °C

6: 95.5 percent / NaI / 0.33 h / Ambient temperature

7: trimethylsilyl chloride, NaI / 1.5 h / Heating

8: 73 percent / NaI / 0.33 h / Ambient temperature

9: 100 percent / 1M NaOH / methanol / 2.5 h / 60 °C

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; titanium tetrachloride; ozone; triphenylphosphine; sodium iodide; zinc; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)80653-0

upstream raw materials:

14,17α-ethanoestra-1,3,5(10)-trien-3,16α,17β-triyl triacetate

14-allyl-3-methoxy-14β-estra-1,3,5(10)-trien-17-one

14β-Allyl-3-methoxy-14β-estra-1,3,5(10),15-tetraen-17-one

14-formylmethyl-3-methoxy-14β-estra-1,3,5(10)-trien-17-one