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Cas Database

100020-76-6

100020-76-6

Identification

  • Product Name:(1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-4-octenoate

  • CAS Number: 100020-76-6

  • EINECS:

  • Molecular Weight:372.548

  • Molecular Formula:C24H36O3

  • HS Code:

  • Mol File:100020-76-6.mol

Synonyms:

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    Relevant articles and documentsAll total 2 Articles be found

    Preparation of 8-Phenylmenthol and Its Diastereomer, 2-epi,ent-8-Phenylmenthol. A Caveat

    Whitesell, James K.,Liu, Chi-Ling,Buchanan, Charles M.,Chen, Hwang-Hsing,Minton, Mark A.

    , p. 551 - 553 (2007/10/02)

    -

    ASYMMETRIC INDUCTION IN THE ENE REACTION OF GLYOXYLATE ESTERS OF 8-PHENYLMENTHOL

    Whitesell, James K.,Bhattacharya, Apurba,Buchanan, Charles M.,Chen, H. H.,Deyo, Don,et al.

    , p. 2993 - 3002 (2007/10/02)

    We recently communicated (J.K.Whitesell, A.Bhattacharya, D.A.Aguilar and K.Henke, J.Chem.Soc.Chem.Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes.We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety of situations that warrants a more complete presentation of these reactions.

    Process route upstream and downstream products

    Process route

    (1R,3R,4S)-8-phenylmenthyl glyoxylate
    84312-20-9

    (1R,3R,4S)-8-phenylmenthyl glyoxylate

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate
    100020-76-6,100101-45-9

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    With tin(IV) chloride;Indichloromethane;at -78 ℃;
    92%
    (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
    100101-42-6

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

    (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-4-octenoate
    100020-76-6

    (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 3 steps
    1: 91 percent / 4-(dimethylamino)pyridine, triethylamine / CH2Cl2 / 1.5 h / 0 °C
    2: 1.) osmium tetraoxide, 2.) sodium periodate / 1.) water, dioxane, RT, 5 min, 2.) RT, 2 h
    3: 1.) tin tetrachloride, 2.) triethylamine / 1.) dichloromethane, -78 deg C, 10 min, 2.) -78 deg C, 6 h
    With dmap; sodium periodate; osmium(VIII) oxide; tin(IV) chloride; triethylamine;Indichloromethane;
    (-)-8-phenylmenthol
    65253-04-5

    (-)-8-phenylmenthol

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate
    100020-76-6,100101-45-9

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 4 steps
    1: 95 percent / p-toluenesulfonic acid monohydrate / benzene / 11 h / Heating
    2: 81 percent / AgNO3 / acetonitrile / 94 h / Ambient temperature
    3: 92 percent / sodium acetate trihydrate / dimethylsulfoxide / 1.17 h / Ambient temperature
    4: 92 percent / SnCl4 / CH2Cl2 / -78 °C
    With sodium acetate; tin(IV) chloride; toluene-4-sulfonic acid; silver nitrate;Indichloromethane; dimethyl sulfoxide; acetonitrile; benzene;
    Multi-step reaction with 3 steps
    1: 87 percent / 4-dimethylaminopyridine, Et3N / CH2Cl2 / 2.2 h / 0 °C
    3: 92 percent / SnCl4 / CH2Cl2 / -78 °C
    With dmap; tin(IV) chloride; triethylamine;Indichloromethane;
    bromoacetic acid (-)-8-phenylmenthol ester
    80595-59-1

    bromoacetic acid (-)-8-phenylmenthol ester

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate
    100020-76-6,100101-45-9

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 3 steps
    1: 81 percent / AgNO3 / acetonitrile / 94 h / Ambient temperature
    2: 92 percent / sodium acetate trihydrate / dimethylsulfoxide / 1.17 h / Ambient temperature
    3: 92 percent / SnCl4 / CH2Cl2 / -78 °C
    With sodium acetate; tin(IV) chloride; silver nitrate;Indichloromethane; dimethyl sulfoxide; acetonitrile;
    (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate
    104197-95-7

    (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate
    100020-76-6,100101-45-9

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    1: 92 percent / sodium acetate trihydrate / dimethylsulfoxide / 1.17 h / Ambient temperature
    2: 92 percent / SnCl4 / CH2Cl2 / -78 °C
    With sodium acetate; tin(IV) chloride;Indichloromethane; dimethyl sulfoxide;
    (-)-8-phenylmenthyl acrylate
    72526-00-2

    (-)-8-phenylmenthyl acrylate

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate
    100020-76-6,100101-45-9

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    2: 92 percent / SnCl4 / CH2Cl2 / -78 °C
    With tin(IV) chloride;Indichloromethane;
    (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate
    100020-75-5

    (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate

    (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-4-octenoate
    100020-76-6

    (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    1: 1.) osmium tetraoxide, 2.) sodium periodate / 1.) water, dioxane, RT, 5 min, 2.) RT, 2 h
    2: 1.) tin tetrachloride, 2.) triethylamine / 1.) dichloromethane, -78 deg C, 10 min, 2.) -78 deg C, 6 h
    With sodium periodate; osmium(VIII) oxide; tin(IV) chloride; triethylamine;
    (1R,3R,4S)-8-phenylmenthyl glyoxylate
    84312-20-9

    (1R,3R,4S)-8-phenylmenthyl glyoxylate

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate
    100020-76-6,100101-45-9

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    With tin(IV) chloride;Indichloromethane;at -78 ℃;
    92%
    (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
    100101-42-6

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

    (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-4-octenoate
    100020-76-6

    (1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 3 steps
    1: 91 percent / 4-(dimethylamino)pyridine, triethylamine / CH2Cl2 / 1.5 h / 0 °C
    2: 1.) osmium tetraoxide, 2.) sodium periodate / 1.) water, dioxane, RT, 5 min, 2.) RT, 2 h
    3: 1.) tin tetrachloride, 2.) triethylamine / 1.) dichloromethane, -78 deg C, 10 min, 2.) -78 deg C, 6 h
    With dmap; sodium periodate; osmium(VIII) oxide; tin(IV) chloride; triethylamine;Indichloromethane;
    (-)-8-phenylmenthol
    65253-04-5

    (-)-8-phenylmenthol

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate
    100020-76-6,100101-45-9

    (-)-8-phenylmenthyl (2S)-2-hydroxy-4-octenoate

    Conditions
    ConditionsYield
    Multi-step reaction with 4 steps
    1: 95 percent / p-toluenesulfonic acid monohydrate / benzene / 11 h / Heating
    2: 81 percent / AgNO3 / acetonitrile / 94 h / Ambient temperature
    3: 92 percent / sodium acetate trihydrate / dimethylsulfoxide / 1.17 h / Ambient temperature
    4: 92 percent / SnCl4 / CH2Cl2 / -78 °C
    With sodium acetate; tin(IV) chloride; toluene-4-sulfonic acid; silver nitrate;Indichloromethane; dimethyl sulfoxide; acetonitrile; benzene;
    Multi-step reaction with 3 steps
    1: 87 percent / 4-dimethylaminopyridine, Et3N / CH2Cl2 / 2.2 h / 0 °C
    3: 92 percent / SnCl4 / CH2Cl2 / -78 °C
    With dmap; tin(IV) chloride; triethylamine;Indichloromethane;

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