(1S)-Exo-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-OL

Base Information

• Chemical Name: (1S)-Exo-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-OL
• CAS No.: 68330-44-9
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.279
• Nikkaji Number: J664.546A
• Wikidata: Q105151228
• Mol file: 68330-44-9.mol

Synonyms:(1S)-EXO-1,2,7,7-TETRAMETHYLBICYCLO[2.2.1]HEPTAN-2-OL;(1S,2S,4S)-2-Methylbornane-2-ol;AKOS006287223

Chemical Property of (1S)-Exo-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-OL

Chemical Property:

• Boiling Point: 208.7±8.0 °C(Predicted)
• PKA: 15.43±0.60(Predicted)
• PSA: 20.23000
• Density: 0.968±0.06 g/cm3(Predicted)
• LogP: 2.58360
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 168.151415257
• Heavy Atom Count: 12
• Complexity: 221

Purity/Quality:

99% ^*data from raw suppliers

(1S)-EXO-1,2,7,7-TETRAMETHYLBICYCLO-[2.2.1]-HEPTAN-2-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(C2)(C)O)C)C
• Isomeric SMILES: C[C@]12CC[C@H](C1(C)C)C[C@]2(C)O

Technology Process of (1S)-Exo-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-OL

There total 6 articles about (1S)-Exo-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-OL 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: 61.0%

(1S,2S,4S)-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,2'-oxirane] (83997-36-8) → 2-methylisoborneol (68330-44-9,812697-60-2)

Guidance literature:

With dibutylmagnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 40 ℃; for 24h; regioselective reaction;

DOI:10.1021/jacs.0c05917

Reference yield:

(1S)-camphor (464-48-2,68546-28-1) + methylmagnesium chloride (676-58-4) → 2-methylisoborneol (68330-44-9,812697-60-2)

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1002/anie.200702496

Reference yield:

(1S)-camphor (464-48-2,68546-28-1) → 2-methylisoborneol (68330-44-9,812697-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfoxide / 16 h / Ambient temperature

2: LiAlH₄ / diethyl ether / 2 h / 0 - 5 °C

With lithium aluminium tetrahydride; In diethyl ether; dimethyl sulfoxide;

DOI:10.1021/ja00340a019

upstream raw materials:

(1S)-camphor

methylmagnesium bromide

(1S,2S,4S)-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,2'-oxirane]

methylmagnesium chloride