(1R)- 6,6'-bis([1,1'-biphenyl]-4-yl)-2,2',3,3'-tetrahydro-1,1'-Spirobi[1H-indene]-7,7'-diol

Base Information

• Chemical Name: (1R)- 6,6'-bis([1,1'-biphenyl]-4-yl)-2,2',3,3'-tetrahydro-1,1'-Spirobi[1H-indene]-7,7'-diol
• CAS No.: 1297613-71-8
• Molecular Formula: C₄₁H₃₂O₂
• Molecular Weight: 556.704
• Mol file: 1297613-71-8.mol

Synonyms:

Chemical Property of (1R)- 6,6'-bis([1,1'-biphenyl]-4-yl)-2,2',3,3'-tetrahydro-1,1'-Spirobi[1H-indene]-7,7'-diol

Chemical Property:

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)- 6,6'-bis([1,1'-biphenyl]-4-yl)-2,2',3,3'-tetrahydro-1,1'-Spirobi[1H-indene]-7,7'-diol

There total 6 articles about (1R)- 6,6'-bis([1,1'-biphenyl]-4-yl)-2,2',3,3'-tetrahydro-1,1'-Spirobi[1H-indene]-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: 94.0%

(S)-6,6'-diiodo-1,1'-spirobiindane-7,7'-diol + 4-biphenylboronic acid (5122-94-1) → (S)-6,6'-di(biphenyl-4-yl)-1,1'-spirobiindane-7,7'-diol (1258327-00-2,1297613-71-8)

Guidance literature:

With 5% Pd(II)/C(eggshell); potassium carbonate; In 1,4-dioxane; water; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo101640z

Reference yield: 92.0%

(R)-6,6'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobis[1H-indole]-7,7'-diphenol (1621066-74-7,1807777-59-8) + 4-biphenylboronic acid (5122-94-1) → (R)-6,6'-di(biphenyl-4-yl)-1,1'-spirobiindane-7,7'-diol (1258327-00-2,1297613-71-8)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; toluene; at 105 - 110 ℃; Inert atmosphere;

DOI:10.1021/jo200302x

Reference yield:

(S)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol → (S)-6,6'-di(biphenyl-4-yl)-1,1'-spirobiindane-7,7'-diol (1258327-00-2,1297613-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / diethyl ether; hexane / 6 h / -78 - 20 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / methanol; chloroform; water / 3 h / Inert atmosphere; Reflux

4.1: 5% Pd(II)/C(eggshell); potassium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; 5% Pd(II)/C(eggshell); sodium hydride; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; chloroform; water; mineral oil; 4.1: Suzuki coupling;

DOI:10.1021/jo101640z

upstream raw materials:

4-biphenylboronic acid

(R)-6,6'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobis[1H-indole]-7,7'-diphenol

Refernces

• 1、 Xu, Fangxi,Huang, Dan,Han, Chao,Shen, Wei,Lin, Xufeng,Wang, Yanguang. "SPINOL-derived phosphoric acids: Synthesis and application in enantioselective Friedel-Crafts reaction of indoles with imines". supporting information; experimental part. p. 8677 - 8680. Retrieved 2011/02/26.