1,1'-SPIROBIINDANE-7,7'-DIOL

Base Information

• Chemical Name: 1,1'-SPIROBIINDANE-7,7'-DIOL
• CAS No.: 223259-63-0
• Molecular Formula: C₁₇H₁₆O₂
• Molecular Weight: 252.313
• Mol file: 223259-63-0.mol

Synonyms:(1S)-2,2',3,3'-Tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol

Chemical Property of 1,1'-SPIROBIINDANE-7,7'-DIOL

Chemical Property:

• Melting Point: 155-156℃
• Boiling Point: 433.0±45.0 °C(Predicted)
• PKA: 9.70±0.20(Predicted)
• Flash Point: 208.9oC
• PSA: 40.46000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 3.27630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(S)-SPINOL ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-SPINOL is used to synthesis a new class of chiral phosphoric acids with spirobiindane as scaffold and employed to catalyze the asymmetric Friedel?Crafts reaction of indoles with imines to afford 3-indolyl methanamines.

Technology Process of 1,1'-SPIROBIINDANE-7,7'-DIOL

There total 42 articles about 1,1'-SPIROBIINDANE-7,7'-DIOL 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: 98.0%

(S)-4,4'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol (636601-27-9,681481-91-4,681481-94-7) → 2,2′,3,3′-tetrahydro-1,1′-spirobi[indene]-7,7′-diol (223137-87-9,223259-62-9,223259-63-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; triethylamine; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1021/jacs.6b11435

Reference yield: 98.0%

(R)-4,4'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol → (R)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol (223137-87-9,223259-62-9,223259-63-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; triethylamine; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1021/jacs.6b11435

Reference yield: 98.0%

(S)-1,1'-spirobiindane-7,7'-diol bismenthyl carbonate → 2,2′,3,3′-tetrahydro-1,1′-spirobi[indene]-7,7′-diol (223137-87-9,223259-62-9,223259-63-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 2h; Heating;

DOI:10.1055/s-2004-831238

upstream raw materials:

7,7'-dimethoxy-1,1'-spirobiindane

1,5-bis(3-methoxyphenyl)-3-pentanone

3-methoxy-benzaldehyde

(1E,4E)-1,5-bis(3-methoxyphenyl)penta-1,4-dien-3-one

Downstream raw materials:

(R)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol

2,2′,3,3′-tetrahydro-1,1′-spirobi[indene]-7,7′-diol

[(R)-1,1'-spirobiindane-7,7'-diyl] diisopropylamidophosphite

Refernces

• 1、 Zhu, Zhouhe,Zhang, Yuqian,Wang, Kai,Fu, Xiying,Chen, Fengjuan,Jing, Huanwang. "Chiral oligomers of spiro-salencobalt(III)X for catalytic asymmetric cycloaddition of epoxides with CO2". . p. 50 - 53. Retrieved 2016/05/10.
• 2、 Li, Shaoyu,Zhang, Ji-Wei,Li, Xian-Lin,Cheng, Dao-Juan,Tan, Bin. "Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives". supporting information. p. 16561 - 16566. Retrieved 2016/12/27.