223137-87-9

Basic information

• Product Name: 2,2',3,3'-Tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol
• Synonyms: 2,2',3,3'-Tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol;2,2',3,3'-Tetrahydro-1,1'-spirobi[indene]-7,7'-diol;2,2',3,3'-Tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol, 99%e.e.;SPINOL
• CAS NO: 223137-87-9
• Molecular Formula: C₁₇H₁₆O₂
• Molecular Weight: 252.31
• Mol File: 223137-87-9.mol

Chemical Properties

• Boiling Point: 433.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.34
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.70±0.20(Predicted)
• CAS DataBase Reference: 2,2',3,3'-Tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2',3,3'-Tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol(223137-87-9)
• EPA Substance Registry System: 2,2',3,3'-Tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol(223137-87-9)

Safety Data

• Hazardous Substances Data: 223137-87-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Spirodiol is utilized as a chiral ligand in organic synthesis, playing a crucial role in the formation of enantioselective reactions. Its chiral properties allow for the creation of specific enantiomers, which are essential in the production of pharmaceuticals and other chiral compounds.
Used in Pharmaceutical Development:
Spirodiol is studied for its potential pharmaceutical applications due to its antioxidant and neuroprotective properties. These characteristics make it a promising candidate for the development of new drugs, particularly those targeting conditions associated with oxidative stress and neurodegeneration.
Used in Resolving Racemic Mixtures:
As a resolving agent for racemic mixtures, spirodiol helps in separating enantiomers, which is vital for obtaining pure compounds with desired biological activities. This application is particularly relevant in the pharmaceutical industry, where the correct enantiomer is crucial for drug efficacy and safety.

Upstream product

• 223137-67-5 1,5-bis(3-methoxyphenyl)-3-pentanone 
• 591-31-1 3-methoxy-benzaldehyde 
• 458533-66-9 (1E,4E)-1,5-bis(3-methoxyphenyl)penta-1,4-dien-3-one 
• 223137-76-6 4,4'-dibromo-7,7'-dimethoxy-1,1'-spirobiindane 
• 116836-15-8 1,5-bis(3-methoxyphenyl)-1,4-pentadien-3-one 
• 100-83-4 meta-hydroxybenzaldehyde 
• 1427054-08-7 1,5-bis(3-hydroxyphenyl)pentan-3-one 
• 223137-87-9 (R)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol 
• 881915-97-5 (1E,4E)-1,5-bis(3-hydroxyphenyl)penta-1,4-dien-3-one 
• 223137-81-3 7,7'-dimethoxy-1,1'-spirobiindane 
• 636601-27-9 (S)-4,4'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol 
• 1427054-10-1 1,5-bis(2-bromo-5-hydroxyphenyl)pentan-3-one 
• 223137-71-1 1,5-bis-(2-bromo-5-methoxyphenyl)-3-pentanone 

Downstream Products

• 223137-87-9 (R)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol 
• 223137-87-9 2,2′,3,3′-tetrahydro-1,1′-spirobi[indene]-7,7′-diol 
• 1286189-15-8 6,6'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol 
• 1286189-16-9 C₃₃H₂₀F₁₂O₂ 
• 500997-67-1 [(R)-1,1'-spirobiindane-7,7'-diyl] diisopropylamidophosphite 
• 500997-68-2 N,N-dicyclohexyl-[(R)-1,1'-spirobiindane-7,7'-diyl]phosphoramidite 
• 656233-47-5 (11aR)-(+)-10,11,12,13-tetrahydrodiindeno[7,1-de:1', 7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine 
• 477559-80-1 N,N-diethyl-[(R)-1,1'-spirobiindane-7,7'-diyl]phosphoramidite 
• 656233-53-3 phenyl-[(R)-1,1'-spirobiindane-7,7'-diyl]phosphite 

Relevant articles and documents

A ligand synthesis of butadiene adhesive

The invention relates to a synthesis method of ligand butadiene adhesive, to 3 - hydroxybenzaldehyde with acetone as the starting material, condensation to obtain the 1, 5 - double-(3 - hydroxy-phenyl) - 1, 4 - isoprene ketone, the 1, 5 - double-(3 - hydr

Chiral oligomers of spiro-salencobalt(III)X for catalytic asymmetric cycloaddition of epoxides with CO2

Several new chiral oligomers of spiro-salenCo(III)X (spiro = 1.1′-spirobiindane-7.7′-diol) complexes have been designed, synthesized, and characterized by nuclear magnetic resonance (NMR), infrared (IR), and elemental analyses, in which, the chiral spiro moieties are first introduced into a scaffold of chiral salenCo catalysts. They were used to catalyze the asymmetric cycloaddition of epoxides with carbon dioxide. Under very mild reaction conditions, a kinetic resolution of racemic epoxides with CO2 was smoothly initiated by these chiral oligomer catalysts with good enantioselectivities, which can be attributed to the match effect between chiral backbones of salen and spiro. High stability and easy recyclability are their major advantages.

Chiral ligand 1,1'-spirobiindane-7,7'-diol synthesis method

The present invention discloses a chiral ligand 1,1'-spirobiindane-7,7'-diol synthesis method, wherein 3-methoxybenzaldehyde is adopted as a starting raw material, and hydroxyaldehyde condensation, hydrogenation reducing, bromination, dehydration cyclizat

Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives

Axially chiral 1,1′-spirobiindane-7,7′-diol (SPINOL) is the most fundamental and important privileged structure from which other chiral ligands containing a 1,1′-spirobiindane backbone are synthesized. Driven by the development of enantioselective syntheses of axially chiral SPINOL derivatives, we have successfully developed the first phosphoric acid-catalyzed asymmetric approach. This approach is highly convergent and functional group tolerant, efficiently providing SPINOLs in good yield with excellent enantioselectivity, thus delivering a practical and straightforward access to this privileged structure. It should be emphasized that the catalyst loading could be decreased to only 0.1 mol% for the preparative-scale synthesis. Furthermore, 4,4′-dimethyl-SPINOL-phosphoric acid was synthesized and applied to catalyze the model reaction for synthesis of enantioenriched SPINOL derivatives.

CHIRAL COMPOUNDS AND COMPOSITIONS CONTAINING THE SAME

The invention relates to a novel class of compounds useful as chiral dopants, which compounds are available in both enantiomeric forms. Another aspect of the invention relates to such compounds having a enantiomeric excess of one enantiomeric form, which are useful in liquid crystal formulations. Such formulations are advantageous in displays and various other products.

Facile synthesis of enantiopure 1,1′-spirobiindane-7,7′-diol and its 4,4′-derivatives: Application in enantioselective addition of diethylzinc to aromatic aldehydes

The enantiopure 1,1′-spirobiindane-7,7′-diol (SPINOL) and its 4,4′-derivatives 4,4′-diiodo-1,1′-spirobiindane-7,7′- diol (DISPINOL) and 4,4′-dimethyl-1,1′-spirobiindane-7,7′-diol (DMSPINOL) have been synthesized effectively via (1S)-(-)-4,4′-dibromo-1, 1′

1,1'-Spirobiindane-7,7'-diol: A novel, C2-symmetric chiral ligand

A novel, C2-symmetric chiral diol (16) was prepared in six steps from m-anisaldehyde and resolved via its bis-L-menthoxycarboxylate.