(R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: (R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide
• CAS No.: 1308740-24-0
• Molecular Formula: C₁₁H₁₈BrNOS
• Molecular Weight: 292.24
• Mol file: 1308740-24-0.mol

Synonyms:(R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide

Chemical Property of (R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide

There total 1 articles about (R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide 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: 83.0%

2-bromocyclohex-1-ene-1-carbaldehyde (38127-47-8) + (R)-2-methylpropane-2-sulfinamide (196929-78-9) → (R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide (1308740-24-0)

Guidance literature:

2-bromocyclohex-1-ene-1-carbaldehyde; With titanium(IV) tetraethanolate; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere;

(R)-2-methylpropane-2-sulfinamide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol201051q

Reference yield: 66.0%

1-bromo-4-butene (5162-44-7) + (R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide (1308740-24-0) → (Rs,1S)-N-[1-(2-bromocyclohex-1-en-1-yl)pent-4-en-1-yl]-2-methylpropane-2-sulfinamide (1308740-33-1) + (Rs,1R)-N-[1-(2-bromocyclohex-1-en-1-yl)pent-4-en-1-yl]-2-methylpropane-2-sulfinamide

Guidance literature:

1-bromo-4-butene; With magnesium; In diethyl ether; at 0 - 20 ℃; for 1h; Inert atmosphere;

(R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide; In tetrahydrofuran; diethyl ether; at -20 - 0 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol201051q

Reference yield:

(R,E)-N-[(2-bromocyclohex-1-en-1-yl)methylene]-2-methylpropane-2-sulfinamide (1308740-24-0) → (S)-1-(2-bromocyclohex-1-en-1-yl)pent-4-en-1-ylamine (1308740-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere

1.2: -20 - 0 °C / Inert atmosphere

2.1: hydrogenchloride / 1,4-dioxane; methanol / 20 °C / Inert atmosphere

With hydrogenchloride; magnesium; In 1,4-dioxane; methanol; diethyl ether;

DOI:10.1021/ol201051q

upstream raw materials:

2-bromocyclohex-1-ene-1-carbaldehyde

(R)-2-methylpropane-2-sulfinamide

Downstream raw materials:

(Rs,1S)-N-[1-(2-bromocyclohex-1-en-1-yl)pent-4-en-1-yl]-2-methylpropane-2-sulfinamide

(S)-1-(2-bromocyclohex-1-en-1-yl)pent-4-en-1-ylamine

(S)-N-[1-(2-bromocyclohex-1-en-1-yl)pent-4-en-1-yl]aniline

(5S,8R)-10-phenyl-2,3,4,5,6,7,8,9-octahydro-1H-5,8-epiminobenzo[7]annulene