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(-)-8-苯基薄荷醇

(-)-8-苯基薄荷醇

CAS号：65253-04-5

英文名：(-)-8-Phenylmenthol

分子式

C16H24O

熔点

密度

0.999g/mLat 20°C(lit.)

分子量

232.361

沸点

130 °C (0.7501 mmHg)

溶解度

信号词

危险品标志

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基本信息

中文名称

(-)-8-苯基薄荷醇

英文名称

(-)-8-Phenylmenthol

中文别名

(-)-8-苯基(2-丙基)-5-甲基环己醇

英文别名

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

CAS号

65253-04-5

分子式

C16H24O

分子量

232.361

精确质量

232.183

PSA

20.23

LOGP

3.7613

编号系统

MDL号

MFCD00010501

PubChem号

24887371

BRN号

3651167

物化性质

外观与性状

透明无色油性液体

密度

0.999g/mLat 20°C(lit.)

沸点

130 °C (0.7501 mmHg)

闪点

>230°F

折射率

n20/D 1.53(lit.)

储存条件

2-8ºC

安全信息

安全说明

S26-S36

WGK Germany

3

危险类别码

R36/37/38

海关编码

2906299090

危险品标志

Xi

生产方法及用途

生产方法

在碘化亚铜催化下，(1R,2S,5R)-(–)-8-苯基薄荷醇可通过苯基溴化镁与(+)-胡薄荷酮反应制备。

用途

手性不对称磷配体的合成(–)-8-苯基薄荷醇与三氯化磷、联苯酚衍生物反应，可以得到不对称有机磷配体 (
式1)。这种配体与金属Ru催化剂一起催化不对称加氢还原反应 (
式2)。作为手性诱导辅基(–)-8-苯基薄荷醇的衍生物可作为不对称诱导的手性助剂用于不对称诱导的合成中，包括分子间与分子内的Diels-Alder反应、双羟基化反应，以及分子内α,β-不饱和8-苯基薄荷醇酸酯的分子内烯化。这些反应的反应速度温和、具有高立体选择性和高反应产率。8-苯基薄荷醇的α-酮酯 (如8-苯基薄荷丙酮酸酯) 被用于酮不对称加成，也适用于不对称光催化加成和亲核烷基化反应。8-苯基薄荷醇的α-亚胺酯与烯烃的烯化可以得到高光学纯度的α-亚胺酸。在有甲基锌试剂参与下， (–)-8-苯基薄荷醇作为手性辅基可以诱导炔基锆化合物对α-酮酸酯的不对称加成 (
式3)。在4-芳基取代的哌啶合成中，有机镁试剂对不饱和醛酮的不对称Michael加成反应可受手性辅基8-苯基薄荷醇的诱导 (
式4)。在手性辅基8-苯基薄荷醇的存在下，不对称Diels-Alder环化反应是(–)-Epibatidine全合成中最关键的一步 (
式5)。

合成路线

共找到4条合成路线 >

(-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon

(-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon

(-)-8-苯基薄荷醇

(-)-8-苯基薄荷醇

上游原料

共找到53个上游原料 >

(1R,2S,5R)-8-Phenylmenthyl N-benzoyl-(R)-alaninate

(1R,2S,5R)-8-Phenylmenthyl N-benzoyl-(R)-alaninate

(3R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2,3-dihydroxy-2-methylbutanoate

(3R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2,3-dihydroxy-2-methylbutanoate

8-Phenylmenthyl (2S,3R)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate

8-Phenylmenthyl (2S,3R)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate

(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R)-2-(cyclohex-2-ene)acetate

(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R)-2-(cyclohex-2-ene)acetate

(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-((R)-cyclopent-2-en-1-yl)acetate

(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-((R)-cyclopent-2-en-1-yl)acetate

(1R)-8-phenylmenthyl (2S)-2-hydroxy-2,6-dimethyl-6-heptenoate

(1R)-8-phenylmenthyl (2S)-2-hydroxy-2,6-dimethyl-6-heptenoate

下游产品

共找到3个下游商品 >

(1R,2S,5R)-(+)-5-甲基-2-(1-甲基-1-苯乙基)氯乙酸环己酯

(1R,2S,5R)-(+)-5-甲基-2-(1-甲基-1-苯乙基)氯乙酸环己酯

[5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] prop-2-enoate

[5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] prop-2-enoate

[5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-oxopropanoate

[5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-oxopropanoate

上游原料

(1R,2S,5R)-8-Phenylmenthyl N-benzoyl-(R)-alaninate (3R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2,3-dihydroxy-2-methylbutanoate 8-Phenylmenthyl (2S,3R)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R)-2-(cyclohex-2-ene)acetate (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-((R)-cyclopent-2-en-1-yl)acetate (1R)-8-phenylmenthyl (2S)-2-hydroxy-2,6-dimethyl-6-heptenoate N-[((1R,2S,5R)-8-phenylmenthoxy)carbonyl]-1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (-)-8-Phenylmenthyl (2S,3R)-3-Amino-5-methyl-2-((triethylsilyl)oxy)hexanoate (1R,4aS,8aR)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 4-oxodecahydronaphthalene-1-carboxylate (2R,5R)-8-phenylmenthone (1R,5S)-7,7-Dichloro-6-oxo-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 溴化苯基镁 (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-3-methylheptanoate (+)-8-苯基薄荷醇 8-Phenylmenthyl (2S,3S)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon [1R-(1α,2β,5α)]-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl oxoacetate tert-butyldimethyl(((E)-4-(((1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl)oxy)buta-1,3-dien-2-yl)oxy)silane 8-phenylmenthol 8-Phenylmenthyl (2S,3R)-2-Hydroxy-5-methyl-3-nitro-hexanoate (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl pyrrolidine-1-carboxylate 长叶薄荷酮 (-)-8-Phenylmenthyl (2S,3R)-3-Amino-2-hydroxy-5-methyl-hexanoate (5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexan-1-one (-)-8-phenylmenthol phenylcarbamate (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2,3-dihydro-1H-pyrrole-1-carboxylate (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-hydroxypyrrolidine-1-carboxylate (-)-8-Phenylmenthyl (2S,3S)-3-Amino-5-methyl-2-((triethylsilyl)oxy)hexanoate (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-3-methyloctanoate (1S,5S)-6-Oxo-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester Phenylglyoxylsaeure-((1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl)ester N-[((1R,2S,5R)-8-phenylmenthoxyl)carbonyl]-2-(3,4-dimethoxyphenyl)ethylamine (2R,6R)-2-(l-phenmenthyloxy)-6-phenyl-4-[(tert-butyldimethylsilyl)-oxy]-2H(5,6)-dihydropyran (1R,2S,5R)-(+)-5-甲基-2-(1-甲基-1-苯乙基)氯乙酸环己酯 (+)-8-phenylmenthyl Z-crotonate (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (R)-3-phenylbutanoate (-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 甲醇 (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-oxopyrrolidine-1-carboxylate (1R,2S,5R)-(-)-8-phenylmenthyl chloroformate (1R,1R,5R)-8-phenylmenthol (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (1S,2S)-1-(diethoxyphosphoryl)-2-methylcyclohex-3-ene carboxylate (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (E)-but-2-enoate (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate 2,2-二甲氧基丙烷

下游产品

(1R,2S,5R)-(+)-5-甲基-2-(1-甲基-1-苯乙基)氯乙酸环己酯 [5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] prop-2-enoate [5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-oxopropanoate