Bicyclo[2.2.1]heptane-2,3-diol, 1,7,7-trimethyl-2-phenyl-, (1R,2S,3R,4S)-

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-2,3-diol, 1,7,7-trimethyl-2-phenyl-, (1R,2S,3R,4S)-
• CAS No.: 31503-17-0
• Molecular Formula: C16H22O2
• Molecular Weight: 246.349
• Mol file: 31503-17-0.mol

Synonyms:(1R,2S,3R,4S)-1,7,7-Trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol;(-)-(1R,2S,3R,4S)-2-endo-Phenyl-2-exo,3-exo-bornandiol;1,7,7-trimethyl-2-phenylbicyclo[2.2.1]heptane-2,3-diol;(-)-(1R,2R,3R,4S)-2-endo-phenyl-2-exo,3-exo-bornandiol;(2S)-1,7,7-trimethyl-2-phenylbicyclo[2.2.1]heptane-2,3-diol;(-)-(1R,2S,3R,4S)-1,7,7-trimethyl-2-phenylbicyclo[2.2.1]heptane-2,3-diol;(1R,2S,3R,4S)-2-phenyl-1,7,7-trimethylbornanediol;

Chemical Property of Bicyclo[2.2.1]heptane-2,3-diol, 1,7,7-trimethyl-2-phenyl-, (1R,2S,3R,4S)-

Chemical Property:

• Melting Point: 115-116 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 348.6±30.0 °C(Predicted)
• PSA: 40.46000
• Density: 1.145±0.06 g/cm3(Predicted)
• LogP: 2.69120

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.1]heptane-2,3-diol, 1,7,7-trimethyl-2-phenyl-, (1R,2S,3R,4S)-

There total 23 articles about Bicyclo[2.2.1]heptane-2,3-diol, 1,7,7-trimethyl-2-phenyl-, (1R,2S,3R,4S)- 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: 55.0%

2-exo-Hydroxy-2-endo-phenylbornan-3-on (959696-54-9) → (-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol (31503-17-0)

Guidance literature:

With diisobutylaluminium hydride; In toluene; 1.) -70 deg C, 2.) 12 h, r.t.;

Reference yield:

(-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-3-(triethylsilyloxy)-bicyclo[2.2.1]heptan-2-one (853911-96-3) → (-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol (31503-17-0)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 45 ℃; for 3h;

DOI:10.1021/jo050207g

Reference yield:

(+)-(1R,4S)-1,7,7-trimethyl-2-(triethylsilyloxy)bicyclo[2.2.1]hept-2-en (853911-89-4) → (-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol (31503-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Oxone; NaHCO₃ / acetone; H₂O / 1 h / 20 °C

2: CeCl₃ / tetrahydrofuran / 0 - 20 °C

3: 5.2 g / acetic acid / H₂O; tetrahydrofuran / 3 h / 45 °C

With Oxone; cerium(III) chloride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; water; acetone;

DOI:10.1021/jo050207g

upstream raw materials:

2-exo-Hydroxy-2-endo-phenylbornan-3-on

(1R,4R)-1,7,7-trimethyl-2-phenylbicyclo[2.2.1]hept-2-ene

(-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-3-(triethylsilyloxy)-bicyclo[2.2.1]heptan-2-one

(+)-(1R,4S)-1,7,7-trimethyl-2-(triethylsilyloxy)bicyclo[2.2.1]hept-2-en

Downstream raw materials:

C₂₂H₂₉BO₄

C₂₂H₂₉BO₄

2-((1R,2S,6R,7S)-1,10,10-Trimethyl-2-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-acrylic acid ethyl ester

C₂₆H₂₉BF₂O₃