(3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

Base Information

• Chemical Name: (3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole
• CAS No.: 76110-78-6
• Molecular Formula: C₁₆H₂₁BO₂
• Molecular Weight: 256.153
• European Community (EC) Number: 807-220-3
• UNII: YYV77I5ODT
• Nikkaji Number: J1.407.899A
• Mol file: 76110-78-6.mol

Synonyms:76110-78-6;(3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole;YYV77I5ODT;Pinanediol phenylboronate, (+)-;(1S,2S,6R,8S)-2,9,9-trimethyl-4-phenyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane;(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole;4,6-Methano-1,3,2-benzodioxaborole, hexahydro-3a,5,5-trimethyl-2-phenyl-, (3aS,4S,6S,7aR)-;UNII-YYV77I5ODT;MFCD28346273;(1S,2S,6R,8S)-2,9,9-trimethyl-4-phenyl-3,5-dioxa-4-boratricyclo[6.1.1.0?,?]decane;(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2- phenyl-4,6-methano-1,3,2-benzodioxaborole;4,6-METHANO-1,3,2-BENZODIOXABOROLE, HEXAHYDRO-3A,5,5-TRIMETHYL-2-PHENYL-, (3AS-(3A.ALPHA.,4.BETA.,6.BETA.,7A.ALPHA.))-;4,6-Methano-1,3,2-benzodioxaborole, hexahydro-3a,5,5-trimethyl-2-phenyl-, (3as-(3aalpha,4beta,6beta,7aalpha))-

Chemical Property of (3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 256.1634601
• Heavy Atom Count: 19
• Complexity: 377

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC2CC3CC(C3(C)C)C2(O1)C)C4=CC=CC=C4
• Isomeric SMILES: B1(O[C@@H]2C[C@@H]3C[C@H]([C@@]2(O1)C)C3(C)C)C4=CC=CC=C4

Technology Process of (3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

There total 12 articles about (3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 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: 93.0%

pinanediol (18680-27-8) + phenylboronic acid (98-80-6) → (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6)

Guidance literature:

In diethyl ether; at 20 ℃;

Reference yield: 33.0%

pinanediol (18680-27-8) + potassium phenyltrifluoborate → (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6)

Guidance literature:

With potassium hydrogen difluoride; In methanol; water; at 22 ℃;

DOI:10.1021/ol025973d

Reference yield:

(-)-4,5-dimethyl-2-phenyl[1.3.2]dioxaborolane (1061181-00-7) + pinanediol (18680-27-8) → (R,R)-2,3-butandiol (24347-58-8) + (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6)

Guidance literature:

In chloroform-d1; at 20 ℃; for 2.5h; Title compound not separated from byproducts.;

DOI:10.1007/s00706-007-0699-x

upstream raw materials:

pinanediol

phenylboronic acid

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate

Downstream raw materials:

(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

(1-phenylmethyl)boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

(+)-pinanediol (αR)-α-chlorobenzylboronate

1-(S)-chloro-2-phenylethylboronic acid (1S,2S,3R,5S)-(+)-pinane-2,3-glycol ester