Pinacol

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H14O2
Molecular Weight	118.1742
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(O)C(C)(C)O

InChI

InChIKey=IVDFJHOHABJVEH-UHFFFAOYSA-N

InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3

HIDE SMILES / InChI

Molecular Formula	C6H14O2
Molecular Weight	118.1742
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric Diels-Alder reactions.	2005 Dec 22	16354072
Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: synthesis of cyclic cis-vicinal diamines.	2005 Nov 21	16261227
Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon.	2006 Dec 8	17137366
The uptake of methyl vinyl ketone, methacrolein, and 2-methyl-3-butene-2-ol onto sulfuric acid solutions.	2006 Feb 23	16480298
Formation of arylboronates by a CuI-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature.	2006 Jan 19	16408890
Studies of low-coordinate iron dinitrogen complexes.	2006 Jan 25	16417365
TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration.	2006 Jul 6	16805561
Novel calixarene hemisphere synthesized via pinacol rearrangement of [2.1.2.1]metacyclophane.	2006 May 11	16671765
Mechanisms of glycerol dehydration.	2006 May 11	16671686
Luminescence tuning of organoboron quinolates through substituent variation at the 5-position of the quinolato moiety.	2006 Nov 9	17078684
Catalyzed tandem reaction of 3-silyloxy-1,5-enynes consisting of cyclization and pinacol rearrangement.	2007	17310486
The skeletal rearrangement of gold- and platinum-catalyzed cycloisomerization of cis-4,6-dien-1-yn-3-ols: pinacol rearrangement and formation of bicyclo[4.1.0]heptenone and reorganized styrene derivatives.	2007 Dec 19	18020448
Enantioselective pinacol coupling of aryl aldehydes catalyzed by chiral Salan-Mo(IV) complexes.	2007 Dec 21	18044917
Samarium(ii) iodide-mediated intramolecular pinacol coupling reactions with cyclopropyl ketones.	2007 Dec 7	18004443
Theoretical study of the role of solvent H2O in neopentyl and pinacol rearrangements.	2007 Jul 15	17345571
Development of fructosyl valine binding polymers by covalent imprinting.	2007 Jun 15	17419046
Palladium-catalyzed cyclization of 1,omega-dienols: multiple ways to intramolecularly trap a carbocation.	2007 Jun 22	17530903
One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes.	2007 Mar 1	17274623
Room temperature-stable electride as a synthetic organic reagent: application to pinacol coupling reaction in aqueous media.	2007 Oct 11	17854199
Stepwise oxygenation of pinacolborane by a rhodiumperoxo complex: detection of an intermediate metal borate and perborate.	2008	18850628
Stereochemical nonrigidity of a chiral rhodium boryl hydride complex: a sigma-borane complex as transition state for isomerization.	2008 Apr 2	18327937
Sigma-borane complexes of iridium: synthesis and structural characterization.	2008 Aug 13	18642912
Activation of B-H bonds by an oxo-rhenium complex.	2008 Dec 21	19153615
Asymmetric reductive Mannich reaction to ketimines catalyzed by a Cu(I) complex.	2008 Dec 3	18998691
Thermometric MIP sensor for fructosyl valine.	2008 Feb 28	17996440
An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane.	2008 Jul 18	18576604
Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations.	2008 Jul 2	18540580
An expeditious one-step entry to the tetracyclic core of integrastatins.	2008 Jul 21	18594725
Sequential Ni-catalyzed borylation and cross-coupling of aryl halides via in situ prepared neopentylglycolborane.	2008 Jun 19	18484730
Gold(I)-catalyzed divergence in the reactivity of 3-silyloxy 1,6-enynes: pinacol-terminated vs claisen-terminated cyclization cascades.	2008 Jun 19	18476705
Efficient amide-directed catalytic asymmetric hydroboration.	2008 Mar 26	18311977
On the role of samarium/HMPA in the post electron-transfer steps in SmI2 reductions.	2008 Mar 6	18247497
Diastereoselective addition of zincated hydrazones to alkenylboronates and stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles.	2008 Nov 19	18950158
Total syntheses of (+)- and (-)-peribysin E.	2008 Oct 15	18783227
Ionic-liquid-promoted decaborane olefin-hydroboration: a new efficient route to 6-R-B10H13 derivatives.	2008 Oct 20	18800789
Diastereoselective synthesis of cyclopentanediols by InCl 3/Al mediated intramolecular pinacol coupling reaction in aqueous media.	2008 Oct 27	18971861
Synthesis, characterization, and reactivity of rhodium(I) acetylacetonato complexes containing pyridinecarboxaldimine ligands.	2008 Oct 6	18774796
Analysis of recognition of fructose by imprinted polymers.	2008 Sep 15	18761164
Pinacol macrocyclization-based route to the polyfused medium-sized CDE ring system of lancifodilactone G.	2008 Sep 4	18683932
Selectivity control in Lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement.	2009	19593831
Diastereoselective intramolecular pinacol couplings of sulfinyl iron(0) diene complexes.	2009 Feb 20	19199665
Demonstration that CobG, the monooxygenase associated with the ring contraction process of the aerobic cobalamin (vitamin B12) biosynthetic pathway, contains an Fe-S center and a mononuclear non-heme iron center.	2009 Feb 20	19068481
Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes: evidence for reduction to vanadium(III).	2009 Jan 21	19140782
Rationally improved chiral Brønsted acid for catalytic enantioselective allylboration of aldehydes with an expanded reagent scope.	2009 Jun 5	19422213
Reduction of benzophenones with SmI2. Post electron transfer processes.	2009 Mar 6	19199659
Unexpected Ti(III)/Mn-promoted pinacol coupling of ketones.	2009 May 1	19334701
Synthesis of 1-borylisoindoles via palladium-catalyzed dehydrogenation/C-H borylation of isoindolines.	2009 May 6	19354214
Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling.	2009 Sep 17	19694459
Dramatic effect of Lewis acids on the rhodium-catalyzed hydroboration of olefins.	2010 Jan 13	19968306
The synthesis and NMR investigation on novel boron derivatives of stavudine.	2010 Jun	20074771

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:18:57 GMT 2023` Edited by `admin` on `Sat Dec 16 04:18:57 GMT 2023`
Record UNII	527QE7I5CO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Pinacol

Systematic Name

English

Pinacone

Common Name

English

2,3-Dimethyl-2,3-dihydroxybutane

Systematic Name

English

2,3-Dihydroxy-2,3-dimethylbutane

Systematic Name

English

2,3-Butanediol, 2,3-dimethyl-

Systematic Name

English

Tetramethylethylene glycol

Systematic Name

English

1,1,2,2-Tetramethylethylene glycol

Systematic Name

English

2,3-Dimethyl-2,3-butanediol

Systematic Name

English

NSC-25943

Code

English

Pinacol [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

6425