<1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-ylidene)-benzenesulfenamide

Base Information

• Chemical Name: <1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-ylidene)-benzenesulfenamide
• CAS No.: 131251-84-8
• Molecular Formula: C₁₈H₂₃NS
• Molecular Weight: 285.453

Synonyms:<1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-ylidene)-benzenesulfenamide

Chemical Property of <1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-ylidene)-benzenesulfenamide

Chemical Property:

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Technology Process of <1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-ylidene)-benzenesulfenamide

There total 3 articles about <1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-ylidene)-benzenesulfenamide 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: 90.0%

N,N-bis(trimethylsilyl)-phenylsulphenamide (17745-52-7) + <1S-(1α,3β,5β,7α)>-1,4,4-trimethyltricyclo<5.2.0.03,5>nonan-8-one (156963-26-7) → <1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.03,5>nonan-8-ylidene)-benzenesulfenamide (131251-84-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(01)80850-4

Reference yield:

δ-3-carene (20296-50-8,19079-29-9) → <1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.03,5>nonan-8-ylidene)-benzenesulfenamide (131251-84-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / zinc / diethyl ether / 1.25 h / 15 °C / sonication

2: 88 percent / ammonium chloride, zinc / methanol / 40 h / Heating

3: 90 percent / 1.1 M tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

With ammonium chloride; tetrabutyl ammonium fluoride; zinc; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4020(01)80850-4

Reference yield:

<1R-(1α,3β,5β,7α)>-9,9-dichloro-1,4,4-trimethyltricyclo<5.2.0.03,5>nonan-8-one (157084-72-5) → <1R-(1α,2β,4β,7α)>-N-(1,4,4-trimethyltricyclo<5.2.0.03,5>nonan-8-ylidene)-benzenesulfenamide (131251-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / ammonium chloride, zinc / methanol / 40 h / Heating

2: 90 percent / 1.1 M tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

With ammonium chloride; tetrabutyl ammonium fluoride; zinc; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)80850-4

upstream raw materials:

N,N-bis(trimethylsilyl)-phenylsulphenamide

<1S-(1α,3β,5β,7α)>-1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-one

δ-3-carene

<1R-(1α,3β,5β,7α)>-9,9-dichloro-1,4,4-trimethyltricyclo<5.2.0.0^3,5>nonan-8-one

Downstream raw materials:

trans-1-methyl-4-(1-methylethenyl)-2-cyclohexaneacetonitrile

((1R,3S,6S)-3,7,7-Trimethyl-bicyclo[4.1.0]hept-3-yl)-acetonitrile

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