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

Base Information

• Chemical Name: (3aS,4S,6S,7aR)-2-Isobutyl-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole
• CAS No.: 84110-34-9
• Molecular Formula: C14H25 B O2
• Molecular Weight: 236.162
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID70511259
• Nikkaji Number: J2.724.868C
• Wikidata: Q72496030
• Mol file: 84110-34-9.mol

Synonyms:84110-34-9;(3aS,4S,6S,7aR)-2-Isobutyl-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole;2-METHYLPROPANEBORONIC ACID (1S,2S,3R,5S)-(+)-2,3-PINANEDIOL ESTER;(1S,2S,6R,8S)-2,9,9-trimethyl-4-(2-methylpropyl)-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane;(1S,2S,6R,8S)-2,9,9-trimethyl-4-(2-methylpropyl)-3,5-dioxa-4-boratricyclo[6.1.1.0^{2,6}]decane;MFCD09837626;QGWQMLAZUPRXGK-FMSGJZPZSA-N;SCHEMBL459674;DTXSID70511259;BCP25879;AKOS015991281;BS-2112;2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole;AC-33917;AM20120643;CS-0154258;H11813;A864178;2-Methyl propyl) boronic acid (1S,2S,3R,5S ) -(+) -2,3-pinanediol ester;(3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-(2-methylpropyl)hexahydro-2H-4,6-methano-1,3,2-benzodioxaborole;(3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-(2-methylpropyl)hexahydro-4,6-methano-1,3,2-benzodioxaborole;2-Methylpropaneboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester (3aS,4S,6S,7aR)-2-Isobutyl-3a,5,5-triMethylhexahydro-4,6-Methanobenzo[d][1,3,2]dioxaborole

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

Chemical Property:

• Boiling Point: 272.3±9.0ºC (760 Torr)
• Flash Point: 118.5±18.7ºC
• PSA: 18.46000
• Density: 0.97±0.1 g/cm3 (20ºC 760 Torr)
• LogP: 3.37070
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 236.1947602
• Heavy Atom Count: 17
• Complexity: 328

Purity/Quality:

98% ^*data from raw suppliers

2-Methylpropaneboronic Acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 6 articles about (3aS,4S,6S,7aR)-2-Isobutyl-3a,5,5-trimethylhexahydro-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: 97.2%

Dihydroxy-isobutyl-boran (84110-40-7) + (+)-pinanediol (57022-61-4,57022-63-6) → 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole (84110-34-9)

Guidance literature:

In diethyl ether; at 20 ℃; for 23h;

Reference yield: 97.0%

Dihydroxy-isobutyl-boran (84110-40-7) + pinanediol (18680-27-8) → 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole (84110-34-9)

Guidance literature:

In diethyl ether;

DOI:10.1016/j.bmcl.2009.04.103

Reference yield: 94.0%

Chloroiodomethane (593-71-5) + (3aS,4S,6S,7aR)-2-isopropyl-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (90084-26-7) → 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole (84110-34-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; boronic ester and ICH2Cl in rigorously dried THF cooled to -78°Cand stirred under Ar during dropwise addn. of 1.6 M n-BuLi in hexane, kept overnight at 20-25°C; concd. in vac., treated with petroleum ether and concd. aq. NH4Cl, org.phase dried over MgSO4, distilled bulb to bulb in vac.;

DOI:10.1021/om00128a038

upstream raw materials:

Dihydroxy-isobutyl-boran

pinanediol

(+)-α-pinene

isobutylmagnesium bromide

Downstream raw materials:

2,5-dichloro-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexa-hydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

Refernces

• 1、 Klein, Markus,Busch, Michael,Friese-Hamim, Manja,Crosignani, Stefano,Fuchss, Thomas,Musil, Djordje,Rohdich, Felix,Sanderson, Michael P.,Seenisamy, Jeyaprakashnarayanan,Walter-Bausch, Gina,Zanelli, Ugo,Hewitt, Philip,Esdar, Christina,Schadt, Oliver. "Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)". supporting information. p. 10230 - 10245. Retrieved 2021/07/26.
• 2、 Hinkes, Stefan P.A.,Klein, Christian D.P.. "Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids". supporting information. p. 3048 - 3052. Retrieved 2019/05/10.