(+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane

Base Information

• Chemical Name: (+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane
• CAS No.: 152458-96-3
• Molecular Formula: C₂₄H₃₈O₂S
• Molecular Weight: 390.631
• Mol file: 152458-96-3.mol

Synonyms:(+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane

Chemical Property of (+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane

There total 23 articles about (+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane 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: 9.0%

(+)-<2'R,6R,7R>-6-methyl-7-(6-methylhept-2-yl)-2-(phenylsulfonyl)bicyclo<4.3.0>-1-nonene (156137-92-7) → (+)-<1R,2'R,5R,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane (96685-52-8) + (+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane (152458-96-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.333333h; Heating;

DOI:10.1080/00397919408011498 DOI:10.1016/0040-4020(96)00147-0

Reference yield:

(+)-<2'R,6R,7R>-6-methyl-7-(6-methylhept-2-yl)-2-(phenylsulfonyl)bicyclo<4.3.0>-1,4-nonadiene (152459-05-7) → (+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane (152458-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 16 h

2: 9 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Heating

With lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/0040-4020(96)00147-0

Reference yield:

(R)-citronellic acid (18951-85-4,57030-77-0) → (+)-<1R,2'R,5S,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane (152458-96-3)

Guidance literature:

Multi-step reaction with 18 steps

1: H₂

2: SOCl₂

3: 1) n-BuLi / 1) THF, -78 deg C, 2) -78 deg C to RT

4: 1) NaN(SiMe₃)2 / 1) THF, -78 deg C, 2) -78 deg C to -50 deg C, 5 h; -50 deg C, 12 h

6: 87 percent / iBu₂AlH / toluene / -78 °C

7: 79 percent / Et₃N / CH₂Cl₂

8: 82 percent / NaHMDS / tetrahydrofuran / -78 °C

9: 97 percent / KOtBu / tetrahydrofuran / -78 °C

10: 98 percent / nBu₄NF / tetrahydrofuran / Ambient temperature

11: 1) (C₅H₅)2ZrCl₂, 2) I₂ / 1) ClCH₂CH₂Cl, 2) THF

12: 90 percent / (Ph₃P)4Pd / toluene; tetrahydrofuran / Ambient temperature

13: 79 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

14: 1) nBuLi / 1) THF, -78 deg C

15: 71 percent / pyridinium dichromate, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

16: 93 percent / (CF₃SO₂)2O, iPr₂NEt / CH₂Cl₂ / 0 °C

17: toluene / 9 h / 115 °C

18: 1) H₂, 2) LiAlH₄ / 1) 10percent Pd/C / 1) EtOAc, 2) THF, reflux, 20 min

With lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; thionyl chloride; zirconocene dichloride; oxalyl dichloride; trifluoromethylsulfonic anhydride; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; toluene;

upstream raw materials:

(+)-<2'R,6R,7R>-6-methyl-7-(6-methylhept-2-yl)-2-(phenylsulfonyl)bicyclo<4.3.0>-1,4-nonadiene

(+)-<2'R,6R,7R>-6-methyl-7-(6-methylhept-2-yl)-2-(phenylsulfonyl)bicyclo<4.3.0>-1-nonene

Grundmann's ketone

thiophenol

Downstream raw materials:

(+)-<1R,2'R,5R,6R,9R>-1-methyl-9-(6-methylhept-2-yl)-5-(phenylsulfonyl)bicyclo<4.3.0>nonane