(R)-(mesityl)phenylmethanol

• 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: (R)-(mesityl)phenylmethanol
• 英文别名: (R)-phenyl-(2,4,6-trimethylphenyl)methanol
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: WEJXJLHQHYCHDK-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,4,6-trimethylbenzhydrol 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-(mesityl)phenylmethanol
  参考文献：
  名称：

  Comparison of CD Spectra of (2-Methylphenyl)- and (2,6-Dimethylphenyl)-phenylmethanols Leads to Erroneous Absolute Configurations

  摘要：

  Enantiopure (2,6-dimethylphenyl)phenylmethanol (+)-(3) and analog (+)-(4) were prepared and their CD spectra were found opposite to that of (2-methylphenyl)phenylmethanol (R)-(-)-(2), the absolute configuration of which was previously established by X-ray crystallography. Therefore the S absolute configuration was once assigned to (+)-3 and (+)-4 . After that we have succeeded in the X-ray analyses of chiral dichlorophthalate esters of (+)-3 and (+)-4 , which clearly indicated R absolute configuration. It is thus evident that comparison of the CD spectra of alcohols 2, 3, and 4 leads to erroneous absolute configurations.

  DOI：

  10.1080/10242430212878

文献信息

• Application of β-Hydroxysulfoximines in Catalytic Asymmetric Phenyl Transfer Reactions for the Synthesis of Diarylmethanols
  作者：Jörg Sedelmeier、Carsten Bolm

  DOI：10.1021/jo7016718

  日期：2007.11.1

  Enantiomerically enriched diarylmethanols have been prepared by catalyzed asymmetric phenyl transfer reactions onto aromatic aldehydes with use of readily available β-hydroxysulfoximines as catalysts. As the aryl source, combinations of diethylzinc with either diphenylzinc or triphenylborane have been applied affording arylphenylmethanols with up to 93% ee in good yields. Various functionalized aldehydes

  对映体富集的二芳基甲醇已经通过使用容易获得的β-羟基磺氧亚砜作为催化剂，通过催化不对称的苯基转移反应到芳族醛上来制备。作为芳基源，已经应用了二乙基锌与二苯基锌或三苯基硼烷的组合，从而以良好的收率提供了具有高达93％ee的芳基苯基甲醇。可以耐受各种官能化的醛和杂环底物，从而产生合成上相关的产品。
• Application of a Planar Chiralη5-Cyclopentadienylrhenium(I)tricarbonyl Complex in Asymmetric Catalysis: Highly Enantioselective Phenyl Transfer to Aldehydes
  作者：Carsten Bolm、Martin Kesselgruber、Nina Hermanns、Jens P. Hildebrand、Gerhard Raabe

  DOI：10.1002/1521-3773(20010417)40:8<1488::aid-anie1488>3.0.co;2-b

  日期：2001.4.17

  as an efficient catalyst precursor for the asymmetric synthesis of diarylmethanol compounds 2 by phenylation of aldehydes. Compared to the corresponding ferrocene derivative, the performance of the cyrhetrene is superior or at least equally as good and gives excellent enantioselectivities even with catalyst loadings as low as 2 mol %.

  一种新型的平面手性乙炔1被认为是通过醛的苯基化反应不对称合成二芳基甲醇化合物2的有效催化剂前体。与相应的二茂铁衍生物相比，环丙三烯的性能优异或至少同样好，并且即使在催化剂负载量低至2摩尔％的情况下，也具有出色的对映选择性。
• Highly Enantioselective Synthesis of Secondary Alcohols using Triphenylborane
  作者：Jens Rudolph、Frank Schmidt、Carsten Bolm

  DOI：10.1002/adsc.200404067

  日期：2004.6

  Asymmetric phenyl transfer reactions with triphenylborane as aryl source and a ferrocene-based catalyst give secondary alcohols in high yields and excellent enantioselectivities.

  以三苯基硼烷为芳基源和二茂铁基催化剂的不对称苯基转移反应可高收率和出色的对映选择性得到仲醇。
• Davies et al., Journal of the Chemical Society, 1954, p. 3474,3478
  作者：Davies et al.

  DOI：——

  日期：——
• SEEBACH, D.;BECK, A. K.;ROGGO, S.;WONNACOTT, A., CHEM. BER., 1985, 118, N 9, 3673-3682
  作者：SEEBACH, D.、BECK, A. K.、ROGGO, S.、WONNACOTT, A.

  DOI：——

  日期：——