[(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane

Base Information

• Chemical Name: [(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane
• CAS No.: 64234-27-1
• Molecular Formula: C10H19 B
• Molecular Weight: 150.072
• DSSTox Substance ID: DTXSID60445953
• Wikidata: Q72513969
• Mol file: 64234-27-1.mol

Synonyms:64234-27-1;[(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane;[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane;((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane;(+)-ipcbh2;DTXSID60445953;ZFWNFCSCXODQSL-BZNPZCIMSA-N;AKOS015902141

Chemical Property of [(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane

Chemical Property:

• PSA: 0.00000
• LogP: 2.11010
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 148.1423307
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [B]C1CC2CC(C1C)C2(C)C
• Isomeric SMILES: [B][C@@H]1C[C@@H]2C[C@H]([C@H]1C)C2(C)C

Technology Process of [(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane

There total 5 articles about [(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]borane 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:

S-Alpine-Boramine → ((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane (64234-27-1)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at 20 ℃; for 1.5h;

Reference yield:

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (7785-70-8,25766-18-1) → ((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane (64234-27-1)

Guidance literature:

In not given; hydroboration of (+)-alpha-pinene; 100% ee;;

DOI:10.1021/ja00213a028

Reference yield:

(+)-α-pinene (7785-70-8,25766-18-1) → ((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane (64234-27-1)

Guidance literature:

With dibromoborane dimethylsulfide; boron tribromide; In dichloromethane; at 0 - 20 ℃; for 2h; diastereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.6b03963

upstream raw materials:

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

(+)-α-pinene

Downstream raw materials:

(S)-(+)-3-methyl-4-penten-1-ol

(-)-(3R)-methyl-4-penten-1-ol

(1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane

(1R,2R)-(-)-ethyl trans-(2-methylcyclohexyl)-n-pentylborinate