(R)-2-piperazino-1,1,2-triphenylethanol | 620120-36-7

• 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: (R)-2-piperazino-1,1,2-triphenylethanol
• 英文别名: (2R)-1,1,2-triphenyl-2-piperazin-1-ylethanol
• CAS: 620120-36-7
• 化学式: C₂₄H₂₆N₂O
• 分子量: 358.483
• InChiKey: RGMHTUAPJDIABG-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-piperazino-1,1,2-triphenylethanol 在 caesium carbonate 、 sodium ascorbate 作用下， 以 乙腈 、 叔丁醇 为溶剂， 反应 141.0h， 生成 (R)-2-(4-(4-(1-benzyl-1H-1,2,3-triazol-4-yl)butyl)piperazin-1-yl)-1,1,2-triphenylethanol
  参考文献：
  名称：

  Assessing the Suitability of 1,2,3-Triazole Linkers for Covalent Immobilization of Chiral Ligands:  Application to Enantioselective Phenylation of Aldehydes

  摘要：

  Alkynyl-functionalized amino alcohols have been covalently supported on azidomethylpolystyrene resins with different levels of functionalization through Cu(I)-catalyzed 1,3-dipolar cycloadditions ("click chemistry"). The resulting 1,2,3-triazole-substituted resins, characterized by different levels of ligand loading and, depending on the nature of the alkynyl-functionalized amino alcohol, the presence of a one-carbon, four-carbon, or eight-carbon linear spacer, have been tested as catalysts in the enantioselective phenyl transfer from zinc to aldehydes. High catalytic activities and enantioselectivities (up to 82% ee) have been recorded. The influence of structural characteristics of the resin on enantioselectivity are discussed, and the limitations in enantiocontrol inherent to the use of a 1,2,3-triazole linker have been rationalized with the help of DFT calculations on model systems.

  DOI：

  10.1021/jo0624952
• 作为产物：
  描述：

  哌嗪 、 (S)-2,2,3-triphenyloxirane 在 lithium perchlorate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以80%的产率得到(R)-2-piperazino-1,1,2-triphenylethanol
  参考文献：
  名称：

  Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups

  摘要：

  本文描述了一种从醛合成对映富集二芳基甲醇的连续流动系统。该系统使用氨基醇功能化的聚苯乙烯树脂作为催化剂，芳基化试剂通过三芳基硼烷与二乙基锌的转金属化方便地制备。

  DOI：

  10.3762/bjoc.5.56

文献信息

• Polystyrene-supported amino alcohol ligands for the heterogeneous asymmetric addition of phenyl zinc reagents to aldehydes
  作者：David Castellnou、Montserrat Fontes、Ciril Jimeno、Daniel Font、Lluís Solà、Xavier Verdaguer、Miquel A. Pericàs

  DOI：10.1016/j.tet.2005.07.112

  日期：2005.12

  A family of polystyrene-supported amino alcohols, characterized by a high catalytic activity in alkyl transfer from zinc to formyl groups has been successfully tested in the enantioselective addition of phenyl zinc reagents to aldehydes to afford chiral diarylmethanols. Enantioselectivities higher than 90% (mean ee 90.5%; eight examples) are recorded with aromatic aldehydes in what represents the first

  在苯基锌试剂对醛的对映选择性加成中，得到手性二芳基甲醇，已成功测试了一系列聚苯乙烯负载的氨基醇，其特征在于从锌到甲酰基的烷基转移具有很高的催化活性。在芳香醛中记录到高于90％的对映选择性（平均90.5％；八个实例），这是首次成功地使用非均质聚合试剂进行醛的苯酚对映控制。
• New Silica-Immobilized Chiral Amino Alcohol for the Enantioselective Addition of Diethylzinc to Benzaldehyde
  作者：José M. Fraile、José A. Mayoral、Jorge Serrano、Miquel A. Pericàs、Lluís Solà、David Castellnou

  DOI：10.1021/ol0355985

  日期：2003.11.1

  chiral amino alcohol has been immobilized on silica by sol-gel synthesis and grafting. The solid prepared according to the latter method led to the best enantioselectivity (77% ee) described for the asymmetric addition of diethylzinc to benzaldehyde using inorganic solids.

  [反应：见正文]通过溶胶-凝胶合成和接枝将一种容易获得的手性氨基醇固定在二氧化硅上。根据后一种方法制备的固体导致使用无机固体将二乙基锌不对称加成到苯甲醛中时具有最佳的对映选择性（77％ee）。
• Polystyrene-Supported (<i>R</i>)-2-Piperazino-1,1,2-triphenylethanol:  A Readily Available Supported Ligand with Unparalleled Catalytic Activity and Enantioselectivity
  作者：David Castellnou、Lluís Solà、Ciril Jimeno、José M. Fraile、José A. Mayoral、Antoni Riera、Miquel A. Pericàs

  DOI：10.1021/jo048310d

  日期：2005.1.1

  DIAGRAMA very active and highly enantioselective catalytic resin, designed for minimal perturbation of the catalytic center by the polymer matrix, has been assembled in two steps from (S)-triphenylethylene oxide, piperazine, and Merrifield resin and tested in the enantioselective ethylation of aldehydes. 1-Arylpropanols of 94-95 % ee are obtained in high yield by the use of only 2 mol % of catalytic resin at 0 degreesC for 4 h.