(1R,2R)-2-methyl-1-phenylbutan-1-ol | 16725-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-2-methyl-1-phenylbutan-1-ol
• CAS: 16725-77-2
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: XYYQWQIEEXLXDX-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (-)-(R)-1-phenyl-2-methyl-butane-1-one 在 三(五氟苯基)硼烷 、 三正丁基氢锡 作用下， 生成 (1R,2R)-2-methyl-1-phenylbutan-1-ol 、 (1S,2R)-2-methyl-1-phenylbutan-1-ol
  参考文献：
  名称：

  Hypercoordination of Boron and Aluminum:  Synthetic Utility as Chelating Lewis Acids

  摘要：

  DOI：

  10.1021/ja9736828

文献信息

• Catalytic enantioselective synthesis of sterically demanding alcohols using di(2°-alkyl)zinc prepared by the refined Charette's method
  作者：Manabu Hatano、Tomokazu Mizuno、Kazuaki Ishihara

  DOI：10.1039/c0cc01301c

  日期：——

  A highly practical, catalytic enantioselective 2°-alkyl addition to aldehydes and ketones was developed. Chiral phosphoramide ligand (1) with salt-free and solvent-free di(2°-alkyl)zinc reagents prepared from (2°-alkyl)MgCl was essential.

  开发了一种高度实用的催化手性选择性2°烷基对醛和酮的加成反应。手性磷酰胺配体（1）与从2°烷基氯化镁制备的无盐、无溶剂的二(2°烷基)锌试剂是关键。
• Chiral Imidazolium Salts for Asymmetric Catalysis
  申请人：Northwestern University

  公开号：US20160075728A1

  公开（公告）日：2016-03-17

  Planar chiral N-heterocyclic carbenes that incorporate an iron sandwich complex into the NHC framework are disclosed for use in organocatalytic and transition metal-catalyzed reactions.

  插入铁三明治配合物到NHC骨架中的平面手性N-杂环卡宾已被披露，用于有机催化和过渡金属催化反应。
• Enantioselective synthesis of α-phenyl- and α-(dimethylphenylsilyl)alkylboronic esters by ligand mediated stereoinductive reagent-controlled homologation using configurationally labile carbenoids
  作者：Adam L. Barsamian、Zhenhua Wu、Paul R. Blakemore

  DOI：10.1039/c5ob00159e

  日期：——

  with a combination of O-(α-lithiobenzyl)-N,N-diisopropylcarbamate and ligand 3,3-bis[(4S)-4,5-dihydro-4-isopropyloxazol-2-yl] pentane in toluene solvent (−78 °C to rt) with MgBr2·OEt2 additive. Enantioenriched α-(dimethylsilylphenylsilyl)alkylboronates were obtained in 35–69% yield and 9–57% ee by reaction of B-alkyl pinacol boronates with a combination of lithio(dimethylphenylsilyl)methyl 2,4,6-triisopropylbenzoate

  在存在规模的双恶唑啉配体的存在下，通过构型不稳定的外消旋锂类胡萝卜素的作用，研究了硼酸酯的扩链，以对映异构地合成两种标题产物。最初的α-苯基烷基硼酸酯的氧化后处理（NaOOH）产生的对映体富集的2°甲醇，通过B-烷基和B-芳基新戊二醇硼酸酯与以下物质的组合反应，收率35-83％，ee达到70-96％。ø - （α-lithiobenzyl） - ñ，ñ -diisopropylcarbamate和配体3,3-双[（4-小号）-4,5-二氢-4- isopropyloxazol -2-基]戊烷在甲苯溶剂中（-78℃至rt）与MgBr 2 ·OEt 2添加剂。通过使B-烷基频哪醇硼酸酯与硫代（二甲基苯基甲硅烷基）甲基2,4,6-三异丙基苯甲酸酯和配体2,2结合反应，可得到对映体富集的α-（二甲基甲硅烷基苯基甲硅烷基）烷基硼酸酯，产率为35-69％，ee为9-57％-双[（4 S）-4,5-二氢
• Chelation of 2-substituted 1-lithoxides: structural and energetic factors of relevance to synthetic organic chemistry
  作者：Michael A. Nichols、Andrew T. McPhail、Edward M. Arnett

  DOI：10.1021/ja00016a045

  日期：1991.7

  A number of lithium 2-(methylamino)-, 2-(dimethylamino)-, 2-methoxy-, and 2-(isopropylthio)-substituted-1-phenyl-1-propoxides were studied as models for asymmetric synthetic strategies for which lithium chelation between two electronegative atoms has frequently been invoked. The heats of formation of these alkoxides were determined by deprotonating the alcohols with lithium bis(trimethylsilyl)amide in a solution calorimeter. Aggregation numbers for the substituted alcohols and their corresponding lithium alkoxides were obtained with freezing point depression and vapor pressure osmometry in THF, benzene, and dioxane. In several cases, solution structures were obtained through H-1, Li-6, and 2D Li-6-H-1 NOE (HOESY) NMR spectroscopy. Solid-state structures of lithium (+)-N-methylpseudoephedrate and (-)-N-methylephedrate (+)-N-methylpseudoephedrate and (-)-N-methylephedrate (as the benzene solvate) were obtained by X-ray crystallography, and both were found to be present as tetramers in which the dimethylamino nitrogen atoms were coordinated to the lithium cations to form five-membered chelate rings. The lithium alkoxides were either tetramers or hexamers in nonpolar solvents; however, the alkoxides' solution structures were very complex in THF as evidenced by several Li-6 resonances observed in the Li-6 NMR spectra at low temperatures. Intramolecular lithium chelation was found to occur in each alkoxide in dioxane and benzene. The enthalpies of chelational stabilization were estimated by comparing their heats of deprotonation with those of nonchelatable 2-alkyl-substituted analogues. The stabilization enthalpies ranged from 5 to 11 kcal/mol per alkoxide molecule.
• US7291744B2
  申请人：——

  公开号：US7291744B2

  公开（公告）日：2007-11-06