(1R,3S,4R,7R,10S,13R,16S)-1,4,12,12-tetramethyl-8-methylidene-11-oxatetracyclo[8.5.1.03,7.013,16]hexadecane

Base Information

• Chemical Name: (1R,3S,4R,7R,10S,13R,16S)-1,4,12,12-tetramethyl-8-methylidene-11-oxatetracyclo[8.5.1.03,7.013,16]hexadecane
• CAS No.: 89002-20-0
• Molecular Formula: C₂₀H₃₂O
• Molecular Weight: 288.473
• Nikkaji Number: J181.769H
• Mol file: 89002-20-0.mol

Synonyms:

Chemical Property of (1R,3S,4R,7R,10S,13R,16S)-1,4,12,12-tetramethyl-8-methylidene-11-oxatetracyclo[8.5.1.03,7.013,16]hexadecane

Chemical Property:

• Vapor Pressure: 4.86E-05mmHg at 25°C
• Boiling Point: 359.6°C at 760 mmHg
• Flash Point: 167°C
• PSA: 9.23000
• Density: 1g/cm³
• LogP: 5.20860
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 288.245315640
• Heavy Atom Count: 21
• Complexity: 465

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2C1CC3(CCC4C3C(CC2=C)OC4(C)C)C
• Isomeric SMILES: C[C@@H]1CC[C@@H]2[C@H]1C[C@]3(CC[C@@H]4[C@@H]3[C@H](CC2=C)OC4(C)C)C

Technology Process of (1R,3S,4R,7R,10S,13R,16S)-1,4,12,12-tetramethyl-8-methylidene-11-oxatetracyclo[8.5.1.03,7.013,16]hexadecane

There total 56 articles about (1R,3S,4R,7R,10S,13R,16S)-1,4,12,12-tetramethyl-8-methylidene-11-oxatetracyclo[8.5.1.03,7.013,16]hexadecane 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: 82.0%

15-cyanoepoxydictymene (158137-45-2) → Epoxydictymene (89002-20-0)

Guidance literature:

With 18-crown-6 ether; In toluene;

DOI:10.1021/ja00091a079

Reference yield: 80.0%

C26H37NO3Se → Epoxydictymene (89002-20-0)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/ja971526v

Reference yield:

(R)-(+)-1-bromo-3-(1-methylethyl)cyclopentene (120264-20-2) → Epoxydictymene (89002-20-0)

Guidance literature:

Multi-step reaction with 26 steps

1: 1.) t-BuLi, 2.) aq. KOH / 1.) pentane, THF, -78 deg C, 3 h, 2.) MeOH, 20 deg C, overnight

3: 1.) LiBH₄, BH₃*THF, 2.) 30percent H₂O₂, 20percent aq. NaOH / 1.) THF, 20 deg C, overnight, 2.) 3 h

4: 83 percent / pyridinium chlorochromate, Al₂O₃ / CH₂Cl₂; diethyl ether / 3 h / Ambient temperature

5: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C to -15 deg C, 1 h, 2.) HMPA, THF, room temp., 4 h

6: 100 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

7: 1.) DMAP, pyridine, 2.) pyridine / 1.) THF, toluene, room temp., 1 h, 2.) benzene, THF, 4 h

8: 25 percent / tris(trimethylsilyl)silane, AIBN / benzene / 2 h / Heating

9: LDA / tetrahydrofuran / 0.5 h / 20 °C

10: DDQ, collidine / benzene / 30 h / 20 °C

11: 1.) Li, NH₃, 2.) pyridinium chlorochromate, Al₂O₃ / 1.) THF, -78 deg C, 30 min, 2.) CH₂Cl₂, room temp., 3 h

12: LDA / tetrahydrofuran / 0.5 h / Ambient temperature

13: 1.) MCPBA, NaHCO₃, 2.) K₂CO₃ / 1.) CH₂Cl₂, 5 h, room temp., 2.) MeOH, 1 h, room temp.

14: 97 percent / diisopropylethylamine / CH₂Cl₂ / 144 h

15: LiAlH₄ / diethyl ether / -78 - 20 °C

16: 90 percent / Martin sulfurane / benzene / 5 h / 60 °C

17: 85 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 3 h / Ambient temperature

18: 80 percent / LiAlH₄ / tetrahydrofuran / 240 h / Heating

19: 86 percent / Martin's sulfurane / benzene / 2 h / 50 °C

20: 1.) BH₃*THF, LiBH₄, 2.) 20percent aq. NaOH, 30percent H₂O₂ / 1.) THF, room temp., 6 h, 2.) THF, 20 deg C, overnight

21: 2.5percent HCl / methanol / 1 h / Heating

22: 43 percent / pyridine / CH₂Cl₂ / Ambient temperature

23: 95 percent / I₂, PhI(OAc)2 / cyclohexane / 50 °C / Irradiation

24: 2.5percent HCl / methanol / 1 h / Heating

25: Bu₃P / tetrahydrofuran / 2 h

26: 80 percent / 30percent H₂O₂ / tetrahydrofuran / 2 h / 0 °C

With pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; aluminum oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; borane-THF; Martins sulfurane; 2,2'-azobis(isobutyronitrile); tributylphosphine; [bis(acetoxy)iodo]benzene; tris-(trimethylsilyl)silane; ammonia; dihydrogen peroxide; iodine; tert.-butyl lithium; lithium; sodium hydrogencarbonate; potassium carbonate; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; benzene;

DOI:10.1021/ja971526v

upstream raw materials:

15-cyanoepoxydictymene

(R)-(+)-1-bromo-3-(1-methylethyl)cyclopentene

(S)-2-((1R,2S,3R)-2-Formyl-3-methyl-cyclopentyl)-propionic acid methyl ester

(3S,3aS,4S,6aR,9R,9aS,10aR)-6-Hydroxymethyl-3-isopropyl-9,10a-dimethyl-tetradecahydro-dicyclopenta[a,d]cycloocten-4-ol

Downstream raw materials:

C₂₇H₃₈BrNO₄

C₂₇H₃₈BrNO₄