N'-(Bicyclo[2.2.1]heptan-2-ylidene)-4-methylbenzene-1-sulfonohydrazide

Base Information

• Chemical Name: N'-(Bicyclo[2.2.1]heptan-2-ylidene)-4-methylbenzene-1-sulfonohydrazide
• CAS No.: 38397-34-1
• Molecular Formula: C₁₄H₁₈N₂O₂S
• Molecular Weight: 278.375
• DSSTox Substance ID: DTXSID30959315
• Mol file: 38397-34-1.mol

Synonyms:DTXSID30959315;38397-34-1;N'-(Bicyclo[2.2.1]heptan-2-ylidene)-4-methylbenzene-1-sulfonohydrazide

Chemical Property of N'-(Bicyclo[2.2.1]heptan-2-ylidene)-4-methylbenzene-1-sulfonohydrazide

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 278.10889899
• Heavy Atom Count: 19
• Complexity: 458

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NN=C2CC3CCC2C3

Technology Process of N'-(Bicyclo[2.2.1]heptan-2-ylidene)-4-methylbenzene-1-sulfonohydrazide

There total 10 articles about N'-(Bicyclo[2.2.1]heptan-2-ylidene)-4-methylbenzene-1-sulfonohydrazide 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:

Norbornan-2-on (497-38-1) + toluene-4-sulfonic acid hydrazide (1576-35-8) → norcamphor tosylhydrazone (38397-34-1,75686-30-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol;

DOI:10.1246/bcsj.66.3532

Reference yield:

5-norbornene-2-carboxylic acid (58001-99-3) → (1S)-2-norbornenone tosylhydrazone (38397-34-1,75686-30-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / diisopropylamine, n-butyllithium / tetrahydrofuran / 3 h / 0 °C

2: 750 mg / lithium aluminium hydride / tetrahydrofuran / Heating

3: 330 mg / sodium metaperiodide / H₂O; methanol / 5.25 h / Ambient temperature; pH 7

4: hydrogen / platinum oxide / diethyl ether / atmospheric pressure

5: 300 mg / methanol / Heating

With sodium periodate; lithium aluminium tetrahydride; n-butyllithium; hydrogen; diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1021/ja00544a009

Reference yield:

(1R,4R)-(+)-norbornenone (16346-63-7) → (1S)-2-norbornenone tosylhydrazone (38397-34-1,75686-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / platinum oxide / diethyl ether / atmospheric pressure

2: 300 mg / methanol / Heating

With hydrogen; platinum(IV) oxide; In methanol; diethyl ether;

DOI:10.1021/ja00544a009

upstream raw materials:

Norbornan-2-on

toluene-4-sulfonic acid hydrazide

((1R,4S)-3-Chloro-bicyclo[2.2.1]hept-2-en-2-yloxy)-trimethyl-silane

(1R,4S)-2-Trimethylsilanyl-3-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-ene

Downstream raw materials:

exo-2-norbornanol

(+/-)-endo-2-norborneol