US 12,291,497 B2Granted

3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol

AssigneeZhejiang University

InventorsXufeng Lin, Huanyu Shan, Qiaoxia Zhou

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Abstract

Provided herein is 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol, which is a compound represented by formula I, or an enantiomer or a raceme thereof. The is prepared with a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-dicarbaldehyde derivative as a starting material through a Baeyer-Villiger oxidation rearrangement reaction and an alkaline hydrolysis reaction. The 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol comprises two gem-dimethyl groups and is a key intermediate for preparing corresponding 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based monophosphine ligands, such as phosphonite ligands, phosphite ligands, phosphoramidite ester ligands, phosphoric acid and phsophonamidate. The 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol skeleton provided herein could be used in chemical industry and has economic practicality and industrial application prospects.

Claims2

Dependent claims

A 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol, being a compound represented by formula I, or an enantiomer thereof:

wherein R1 is selected from the group consisting of hydrogen, C1-C10 alkyl or perfluoroalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy or perfluoroalkoxy, unsubstituted or substituted aryloxy, unsubstituted or substituted heteroaryloxy, unsubstituted or substituted arylmethyleneoxy, unsubstituted or substituted heteroarylmethyleneoxy, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl;
and R2 and R3 are each independently selected from the group consisting of hydrogen, halogen, C1-C10 alkyl or perfluoroalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy or perfluoroalkoxy, unsubstituted or substituted aryloxy, unsubstituted or substituted heteroaryloxy, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl;
wherein the substituted aryloxy, the substituted aryl or the substituted heteroaryl has one or more substituents each independently selected from the group consisting of halogen, N-dimethylamino, C1-C4 alkyl or perfluoroalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy or perfluoroalkoxy, methylenedioxy, aryl, aryloxy, and heteroaryl, and the heteroaryl is C5-C14 heteroaryl.

Dependencies are inferred from the claim text.

Facts

Application: 17/700,503Filed 22 Mar 2022 · continuation in part
Published: US 2022/0213015 A17 Jul 2022
Granted: 6 May 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07C 39/14
Polycyclic with no unsaturation outside the aromatic rings: with at least one hydroxy group on a condensed ring system containing two rings
C07C 43/21
Having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring: containing rings other than six-membered aromatic rings
C07C 2603/40
Ortho- or ortho- and peri-condensed systems: containing four condensed rings
C07C 2603/96
Containing "not free" spiro atoms: containing at least one ring with less than six members

Family

PCT/CN2018/086893Parent of this continuation-in-part · filed 15 May 2018
US 2022/0213015 A1Pre-grant publication · published 7 Jul 2022
Application17/040,550Parent of this continuation-in-part
US 11,377,457 B2Parent of this continuation-in-part
US 2021/0070789 A1Published application
US 12,291,497 B2This patent

From the US filing history. Foreign family members aren’t listed.