(3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

Base Information

Chemical Name:(3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one
CAS No.:105803-42-7
Molecular Formula:C₁₇H₂₄O₃
Molecular Weight:276.376
Hs Code.:

Synonyms:(3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

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Chemical Property of (3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

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Technology Process of (3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

There total 19 articles about (3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one 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: 92.0%

: 105803-40-5
3-hydroxy acetal silyl ether

: 105803-42-7
(3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

Guidance literature:: With sulfuric acid; In acetonitrile; at 23 ℃; for 16h;
DOI:10.1021/jo00389a038

Reference yield:

: 51592-71-3
8,8-dichlorobicyclo<4.2.0>oct-2-en-7-one

: 105803-42-7
(3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

Guidance literature:: Multi-step reaction with 6 steps

1: via bakers yeast reduction

2: 46 percent / Zn / acetic acid / 5 h / 80 °C

3: β-naphthalenesulfonic acid / benzene / 2 h / 90 °C

4: 1.) N-bromoacetamide, 2.) aq. K₂CO₃ / 1.) acetone, 20 deg C, 16 h, 2.) 48 h

5: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, 0 deg C, 15 min, 2.) -78 deg C, 90 min

6: 0.5 N aq. H₂SO₄ / acetonitrile / 16 h / 20 °C

With n-butyllithium; naphthalene-2-sulfonate; sulfuric acid; boron trifluoride diethyl etherate; potassium carbonate; zinc; N-bromoacetamide; In acetic acid; acetonitrile; benzene;
DOI:10.1021/jo00256a011

Reference yield:

: 97563-45-6,105880-38-4,128241-52-1,4187-88-6
1-cyclohexylprop-2-yn-1-ol

: 105803-42-7
(3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C

2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h

3: 71 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C

5: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C

6: 55.6 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

7: 92 percent / 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C

With chromium(VI) oxide; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; (S)-alpine borane; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo00389a038