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Cas Database

100101-42-6

100101-42-6

Identification

  • Product Name:(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol

  • CAS Number: 100101-42-6

  • EINECS:

  • Molecular Weight:232.366

  • Molecular Formula: C16H24O

  • HS Code:

  • Mol File:100101-42-6.mol

Synonyms:(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol

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Relevant articles and documentsAll total 8 Articles be found

Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions

Maeda, Hajime,Koshio, Norihiro,Tachibana, Yuko,Chiyonobu, Kazuhiko,Konishi, Gen-ichi,Mizuno, Kazuhiko

, p. 7 - 17 (2017/09/12)

By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (?)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(?)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furanmethanol take place in both the ground and excited states. The results of computational studies show that geometries of C2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.

Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol

Crossley, Steven W. M.,Martinez, Ruben M.,Guevara-Zuluaga, Sebastián,Shenvi, Ryan A.

, p. 2620 - 2623 (2016/06/15)

Hydrogen atom transfer (HAT) circumvents a disfavored Friedel-Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified by 8-phenylmenthol. High stereoselectivity is observed in related systems. This use of HAT significantly extends the chiral pool from the inexpensive monoterpene isopulegol.

Enantioselective synthesis of [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept- 5-en-3-yl]methanol via Aza-Diels-Alder reaction

Fernández, Franco,García-Mera, Xerardo,Vale, Maria Luísa C.,Rodríguez-Borges, José Enrique

, p. 319 - 321 (2007/10/03)

The asymmetric aza-Diels-Alder reaction of the 8-phenylneomenthyl (or 8-phenylisomenthyl) glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-

A new, convenient synthesis of the chiral auxiliary (+)-8-phenylisomenthol

Fernández, Franco,García-Mera, Xerardo,Enrique Rodríguez-Borges, José,Manuel Blanco, José

, p. 5239 - 5240 (2007/10/03)

A new, straitghtforward and efficient method for preparing (+)-8-phenylisomenthol 1 from its diastereomer (+)-8-phenylisoneomenthol 2 is described. Conversion of 2 to (+)-8-phenyl-2-menthene 5, followed by oxidation to the corresponding (+)-trans-epoxide 6 and reduction of 6 with LiBEt3H afforded 1 in 78% overall yield.

Synthesis and characterization of all stereoisomers of 8-phenylmenthol

Fernandez, Franco,Garcia-Mera, Xerardo,Lopez, Carmen,Rodriguez, Gonzalo,Rodriguez-Borges, Jose Enrique

, p. 4805 - 4815 (2007/10/03)

New, improved and/or specific syntheses of the diastereoisomers of (-)-8-phenylmenthol are described. The configurations of these products, usable as chiral auxiliaries, were confirmed by X-ray diffractometry of their 3,5-dinitrobenzoates.

Process route upstream and downstream products

Process route

(5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone
205057-17-6

(5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With sodium; isopropyl alcohol; In toluene; Inert atmosphere; Reflux;
4.929 g
(2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanone
104870-79-3

(2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanone

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

(1R,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
104870-80-6

(1R,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol

(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
100101-42-6

(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol

(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexan-1-ol
104870-75-9

(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexan-1-ol

Conditions
Conditions Yield
With sodium; isopropyl alcohol; In toluene; for 3h; Heating;
56%
21%
10%
5%
(5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone
205057-17-6

(5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
100101-42-6

(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol

Conditions
Conditions Yield
With sodium; In isopropyl alcohol; toluene; for 8h; Overall yield = 88 %; Overall yield = 48.9 g; Reflux;
~ 74 % de
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: copper(I) bromide / diethyl ether / 0.5 h / -20 °C / Inert atmosphere
1.2: -20 °C / Inert atmosphere
1.3: 3 h / Reflux
2.1: sodium; isopropyl alcohol / toluene / Inert atmosphere; Reflux
With sodium; isopropyl alcohol; copper(I) bromide; In diethyl ether; toluene;
(R)-2-Isobutyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
126378-69-6,126378-70-9

(R)-2-Isobutyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

2(R)-(2-methypropyl)-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone
126454-97-5

2(R)-(2-methypropyl)-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone

Hydroxy-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
105229-98-9

Hydroxy-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Conditions
Conditions Yield
With methanol; sodium methylate; for 16h; Heating;
92%
Conditions
Conditions Yield
Multi-step reaction with 3 steps
2: toluene; tetrahydrofuran / -78 °C
3: NaOCH3, CH3OH / 16 h / Heating
With methanol; sodium methylate; In tetrahydrofuran; toluene;
Multi-step reaction with 3 steps
2: toluene; tetrahydrofuran / -78 °C
3: 1.) NaOCH3, CH3OH; 2.) K2CO3 / 1.) 16 h, reflux, 2.) aq. CH3OH, 2 h, r.t.
With methanol; sodium methylate; potassium carbonate; In tetrahydrofuran; toluene;
Multi-step reaction with 2 steps
1: 1. n-BuLi / 1.) THF, -78 deg C, 15 min., 2.) THF, -78 deg C to r.t.
2: 1.) NaOCH3, CH3OH; 2.) K2CO3 / 1.) 16 h, reflux, 2.) aq. CH3OH, 2 h, r.t.
With methanol; n-butyllithium; sodium methylate; potassium carbonate;
4-Methoxy-1-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride
144375-66-6

4-Methoxy-1-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: toluene; tetrahydrofuran / -78 °C
2: NaOCH3, CH3OH / 16 h / Heating
With methanol; sodium methylate; In tetrahydrofuran; toluene;
Multi-step reaction with 2 steps
1: toluene; tetrahydrofuran / -78 °C
2: 1.) NaOCH3, CH3OH; 2.) K2CO3 / 1.) 16 h, reflux, 2.) aq. CH3OH, 2 h, r.t.
With methanol; sodium methylate; potassium carbonate; In tetrahydrofuran; toluene;
(R)-2-Isobutyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
126378-69-6,126378-70-9

(R)-2-Isobutyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Conditions
Conditions Yield
With methanol; sodium methylate; potassium carbonate; Multistep reaction; 1.) 16 h, reflux, 2.) aq. CH3OH, 2 h, r.t.;
Conditions
Conditions Yield
C16H22O3S; With tris(2,2,6,6-tetramethyl-3,5-heptanedionato) manganese (III); manganese(III) triacetate dihydrate; In isopropyl alcohol; at 4 ℃; for 1h; Inert atmosphere;
With tert.-butylhydroperoxide; phenylsilane; In hexane; isopropyl alcohol; for 336h; Inert atmosphere;
68%
Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: pyridine / 12 h / 0 °C / Inert atmosphere
2.1: tris(2,2,6,6-tetramethyl-3,5-heptanedionato) manganese (III); manganese(III) triacetate dihydrate / isopropyl alcohol / 1 h / 4 °C / Inert atmosphere
2.2: 336 h / Inert atmosphere
With pyridine; tris(2,2,6,6-tetramethyl-3,5-heptanedionato) manganese (III); manganese(III) triacetate dihydrate; In isopropyl alcohol;

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