threo-2-Methyl-1-phenylbutanol-(1) | 16725-80-7

• 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: threo-2-Methyl-1-phenylbutanol-(1)
• 英文别名: (1R,2S)-1-Phenyl-2-methyl-butylalkohol；(1R,2S)-2-methyl-1-phenylbutan-1-ol
• CAS: 16725-80-7
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: XYYQWQIEEXLXDX-GXSJLCMTSA-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：

  2-甲基-1-苯基-丙-2-烯-1-酮 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 氢气 、 C₄₆H₆₆FeNO₂P 、 sodium hydroxide 作用下， 以 正己烷 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 42.0h， 以99%的产率得到threo-2-Methyl-1-phenylbutanol-(1)
  参考文献：
  名称：

  Ir/f-Ampha配合物催化烯酮的不对称顺序氢化：获得具有两个连续手性中心的手性醇的一般途径

  摘要：

  通过使用铱/f-Ampha 配合物作为催化剂，开发了一种通用且高效的 α,β-不饱和酮的不对称顺序氢化方法，以高收率提供具有两个连续立体中心的相应手性醇，并具有优异的非对映和对映选择性（高达 99% 的产率，>20 : 1 dr 和 >99% ee）。对照实验表明，烯酮的 C C 和 C O 键依次氢化，最终的立体选择性由酮的动态动力学拆分决定。此外，DFT 计算表明，外球途径参与了 C C 和 C的减少。O 烯酮键。该方法的合成效用通过克级反应和极低催化剂负载量 (S/C = 20 000) 和获得抗哮喘药物 CP-199,330 的关键手性中间体的简明合成路线得到证明。

  DOI：

  10.1039/d1sc05963g

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。
• 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.
• COMPOUNDS AND METHODS FOR THE PREVENTION AND TREATMENT OF TUMOR METASTASIS AND TUMORIGENESIS
  申请人：The United States of America, as represented by the Secretary, Dept of Health and Human Services

  公开号：US20170260192A1

  公开（公告）日：2017-09-14

  The disclosure provides compounds for reducing the prevalence of the perinucleolar compartment in cells, for example, of formula (I), wherein R 1 , R 2 , R 3 , and R 4 are as defined herein, that are useful in treating a disease or disorder associated with increased prevalence of the perinucleolar compartment, such as cancer. Also disclosed is a composition containing a pharmaceutically acceptable carrier and at least one compound embodying the principles of the invention, and a method of treating or preventing cancer in a mammal.
• US7291744B2
  申请人：——

  公开号：US7291744B2

  公开（公告）日：2007-11-06