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

Patent metadata

Field	Value
Publication number	US-12291497-B2
Application number	US-202217700503-A
Country	US
Kind code	B2
Filing date	Mar 22, 2022
Priority date	May 15, 2018
Publication date	May 6, 2025
Grant date	May 6, 2025

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.

First claim

What is claimed is:

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

wherein R 1 is selected from the group consisting of hydrogen, C 1 -C 10 alkyl or perfluoroalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 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 R 2 and R 3 are each independently selected from the group consisting of hydrogen, halogen, C 1 -C 10 alkyl or perfluoroalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 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, C 1 -C 4 alkyl or perfluoroalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy or perfluoroalkoxy, methylenedioxy, aryl, aryloxy, and heteroaryl, and the heteroaryl is C 5 -C 14 heteroaryl.

2. The 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol of claim 1 , wherein the compound represented by formula I is any one of the following compounds, or an enantiomer or a raceme thereof:

Assignees

• Univ Zhejiang

Inventors

• Lin Xufeng
• Shan Huanyu
• Zhou Qiaoxia

Classifications

• C07C43/21

  containing rings other than six-membered aromatic rings · CPC title

• C07C2603/40

  containing four condensed rings · CPC title

• C07C2603/96

  containing at least one ring with less than six members · CPC title

• C07C39/14 Primary

  with at least one hydroxy group on a condensed ring system containing two rings · CPC title