(+)-(S)-methoxy-1,2-diphenylethanone | 82572-27-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+)-(S)-methoxy-1,2-diphenylethanone
• 英文别名: (S)-benzoin methyl ether；benzoin methyl ether；Ethanone, 2-methoxy-1,2-diphenyl-, (2S)-；(2S)-2-methoxy-1,2-diphenylethanone
• CAS: 82572-27-8
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: BQZJOQXSCSZQPS-HNNXBMFYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  343.4±30.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(S)-methoxy-1,2-diphenylethanone 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以85%的产率得到(+)-erythro-α,β-diphenyl-β-hydroxyethanol methyl ether
  参考文献：
  名称：

  Asymmetric synthesis of the methyl and benzyl ethers of erythro-.alpha.,.beta.-diphenyl-.beta.-hydroxyethanol and erythro-.alpha.,.beta.-diphenyl-.beta.-hydroxyethylamine from (+)-(S)-benzoin

  摘要：

  DOI：

  10.1021/jo00269a054
• 作为产物：
  描述：

  安息香甲基醚 在 zeolite with (D)-diethyl-tartarate 作用下， 生成 (+)-(S)-methoxy-1,2-diphenylethanone
  参考文献：
  名称：

  Supramolecular control of photochemical enantiomeric induction and radical pair recombination in zeolites

  摘要：

  Geminate radical pairs are formed from the alpha-photocleavage of aryl ketones within the supercage of zeolites which has been modified with chiral guest molecules. Herein, we report the supramolecular structure and dynamic control of both the enantiomeric selectivity and probability of the recombination of the radical pairs. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00426-7

文献信息

• HPLC enantioseparation on a homochiral MOF–silica composite as a novel chiral stationary phase
  作者：Koichi Tanaka、Toshihide Muraoka、Yasuhiro Otubo、Hiroki Takahashi、Atsushi Ohnishi

  DOI：10.1039/c5ra26520g

  日期：——

  frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal–organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers

  色谱对映体分离的手性固定相开发的最后一个领域涉及同手性金属-有机骨架（MOF）。以对映体（R）-2,2'-二羟基-1,1'-双萘-6,6'-二羧酸为起始原料，制备了三种均手性MOF，进一步用作高性能液体的手性固定相色谱分离各种消旋亚砜，仲醇，β-内酰胺，安息香，黄烷酮和环氧化物的对映异构体。实验结果表明，对映体分离具有出色的性能，并强调了在手性MOF色谱柱上进行对映体分离是可行的。
• Forming Stereogenic Centers in Acyclic Systems from Alkynes
  作者：Roxane Vabre、Biana Island、Claudia J. Diehl、Peter R. Schreiner、Ilan Marek

  DOI：10.1002/anie.201504756

  日期：2015.8.17

  This method provides access to functionalized products in which three new carbon–carbon bonds and two to three stereogenic centers, including a quaternary one, were created in acyclic systems in a single‐pot operation from simple alkynes.

  合并的碳金属化/锌同源性，然后与α-杂取代的醛和亚胺反应，通过椅子状过渡结构进行，传入醛残基的取代基优先占据伪轴向位置，以避免两个gauche相互作用。轴向上的杂原子产生螯合的中间体（而不是α-氯醛和亚胺的Cornforth-Evans过渡结构），从而导致烯丙基化反应中的表面差异。这种方法提供了功能化产品的访问途径，在该产品中，简单炔烃通过单罐操作在无环系统中创建了三个新的碳-碳键和两个至三个立体异构中心，其中包括一个四元立体中心。
• [EN] NEW CHIRAL STATIONARY PHASES FOR CHROMATOGRAPHY BASED ON AROMATIC ALLYL AMINES<br/>[FR] NOUVELLES PHASES STATIONNAIRES CHIRALES POUR CHROMATOGRAPHIE À BASE D'AMINES D'ALLYLE AROMATIQUES
  申请人：RUDJER BOSKOVIC INST

  公开号：WO2009109792A1

  公开（公告）日：2009-09-11

  New chiral stationary phases (CSPs) based on chiral selectors covalently bound on a solid support were prepared. Chiral selectors were obtained from enantiomerically pure aromatic amines and 3,5-dinitrobenzoic acid and then linked to the support surface through the allylic double bond. Such obtained materials allow enantioseparation of racemates or enantiomerically enriched compounds. These chiral stationary phases can be used as fillings in chromatographic columns for enantiomer separation of naproxen type drugs and other similar non-steroidal anti-inflammatory drugs (NSAID) by means of high performance liquid chromatography on both the analytical and preparative scale.

  基于手性选择剂共价结合在固体支持上的新手性固定相（CSPs）已经制备。手性选择剂是从对映异构纯芳香胺和3,5-二硝基苯甲酸中获得的，然后通过烯丙基双键连接到支持表面。这样获得的材料可以用于拆分混合物或对映富集化合物的手性分离。这些手性固定相可以作为色谱柱中的填料，通过高效液相色谱在分析和制备尺度上对萘普生类药物和其他类似的非甾体类抗炎药物（NSAID）进行对映异构体分离。
• Nanocellulose Derivative/Silica Hybrid Core-Shell Chiral Stationary Phase: Preparation and Enantioseparation Performance
  作者：Xiaoli Zhang、Litao Wang、Shuqing Dong、Xia Zhang、Qi Wu、Liang Zhao、Yanping Shi

  DOI：10.3390/molecules21050561

  日期：——

  Core-shell silica microspheres with a nanocellulose derivative in the hybrid shell were successfully prepared as a chiral stationary phase by a layer-by-layer self-assembly method. The hybrid shell assembled on the silica core was formed using a surfactant as template by the copolymerization reaction of tetraethyl orthosilicate and the nanocellulose derivative bearing triethoxysilyl and 3,5-dimethylphenyl groups. The resulting nanocellulose hybrid core-shell chiral packing materials (CPMs) were characterized and packed into columns, and their enantioseparation performance was evaluated by high performance liquid chromatography. The results showed that CPMs exhibited uniform surface morphology and core-shell structures. Various types of chiral compounds were efficiently separated under normal and reversed phase mode. Moreover, chloroform and tetrahydrofuran as mobile phase additives could obviously improve the resolution during the chiral separation processes. CPMs still have good chiral separation property when eluted with solvent systems with a high content of tetrahydrofuran and chloroform, which proved the high solvent resistance of this new material.

  通过逐层自组装方法，成功制备了在混合壳中具有纳米纤维素衍生物的核壳硅微球作为手性固定相。在硅核上组装的混合壳是通过表面活性剂作为模板，通过正硅酸四乙酯与带有三乙氧基硅烷基和3,5-二甲基苯基的纳米纤维素衍生物的共聚反应形成的。对所得的纳米纤维素混合核壳手性填料（CPMs）进行了表征并装入色谱柱，通过高效液相色谱法评估了其手性分离性能。结果表明，CPMs具有均匀的表面形貌和核壳结构。在正相和反相模式下，各种类型的手性化合物均被有效地分离。此外，作为流动相添加剂的氯仿和四氢呋喃可以明显提高手性分离过程中的分辨率。当用四氢呋喃和氯仿含量高的溶剂体系洗脱时，CPMs仍然具有良好的手性分离性能，这证明了这种新材料具有很高的耐溶剂性。
• Flash chiral chromatography using carbohydrate carbamate-coated silica
  作者：Stephen A. Matlin、Sally J. Grieb、Ana M. Belenguer

  DOI：10.1039/c39950000301

  日期：——

  Enantiomers of many chiral compounds are resolved rapidly on a preparative scale by passage through a column packed with flash chromatography silica which has been physically coated with a carbohydrate carbamate.

  许多手性化合物的对映体都可以通过闪速色谱硅胶填料柱快速制备分离。