(1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE

Base Information

• Chemical Name: (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE
• CAS No.: 539834-16-7
• Molecular Formula: C37H54N2O2
• Molecular Weight: 558.84
• Mol file: 539834-16-7.mol

Synonyms:2,2'-[(1S,2S,4S,5S)-BICYCLO[2.2.1]HEPTANE-2,5-DIYLBIS(NITRILOMETHYL)]BIS(4,6-DI-TERT-BUTYLPHENOL);(1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE

Chemical Property of (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 254 °C
• Refractive Index: 1.559
• Boiling Point: 625.103°C at 760 mmHg
• PKA: 13.33±0.40(Predicted)
• Flash Point: 429.158°C
• Density: 1.058g/cm³

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1S,2S,4S,5S)-2,5-Bis(3,5-di-tert-butyl-2-hydroxybenzylideneamino)bicyclo[2.2.1]heptane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1S,2S,4S,5S)-2,5-Bis(3,5-di-tert-butyl-2-hydroxybenzylideneamino)bicyclo[2.2.1]heptane is a ligand used in the preparation of chromium-based catalysts for the asymmetric Nozaki-Hiyama-Kishi addition of aldehydes and allyl and vinyl halides.

Technology Process of (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE

There total 22 articles about (1S,2S,4S,5S)-2,5-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYBENZYLIDENEAMINO)BICYCLO[2.2.1]HEPTANE 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: 86.0%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + endo,endo-2,5-diaminobicyclo[2.2.1]heptane (698353-37-6) → 2,2'-[endo,endo-bicyclo[2.2.1]heptane-2,5-diylbis(nitrilomethylidyne)]bis(4,6-di-tert-butylphenol) (539834-16-7)

Guidance literature:

In ethanol; Heating;

DOI:10.1021/jo035841d

Reference yield: 81.0%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + (1S,2S,4S,5S)-2,5-diamino-bicyclo[2.2.1]heptane (698353-42-3,698353-37-6) → 2,2'-[(1S,2S,4S,5S)-bicyclo[2.2.1]heptane-2,5-diylbis(nitrilomethylidyne)]bis(4,6-di-tert-butylphenol) (539834-16-7)

Guidance literature:

In ethanol; at 20 ℃; for 2h;

DOI:10.1021/jo035841d

Reference yield:

(1R,2R,4R,5R)-2,5-bis[(4-methylphenyl)sulfonylamido]bicyclo[2.2.1]heptane (698353-39-8) → 2,2'-[(1R,2R,4R,5R)-bicyclo[2.2.1]heptane-2,5-diylbis(nitrilomethylidyne)]bis(4,6-di-tert-butylphenol) (539834-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Li; NH₃ / -35 °C

With ammonia; lithium;

DOI:10.1021/jo035841d

upstream raw materials:

3,5-di-tert-butyl-2-hydroxybenzaldehyde

(1R,2R,4R,5R)-2,5-diaminobicyclo[2.2.1]heptane

(1R,2S,4R,5S)-exo,exo-bicyclo[2.2.1]heptane-2,5-diol

bicyclo[2.2.1]hepta-2,5-diene

Refernces

• 1、 Berkessel, Albrecht,Menche, Dirk,Sklorz, Christoph A.,Schroeder, Michael,Paterson, Ian. "A highly enantioselective catalyst for the asymmetric Nozaki-Hiyama-Kishi reaction of allylic and vinylic halides". . p. 1032 - 1035. Retrieved 2007/10/03.