N,N-dibenzyl-1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-amine | 1427036-71-2

• 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: N,N-dibenzyl-1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-amine
• 英文别名: (1R,2S)-N,N-dibenzyl-1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-amine
• CAS: 1427036-71-2
• 化学式: C₂₉H₃₆BNO₂
• 分子量: 441.421
• InChiKey: YPAXKCACESYJSH-WNCULLNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-amine 在 sodium perborate tetrahydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 C₂₃H₂₅NO
  参考文献：
  名称：

  Regioselective and Stereospecific Copper-Catalyzed Aminoboration of Styrenes with Bis(pinacolato)diboron and O-Benzoyl-N,N-dialkylhydroxylamines

  摘要：

  A Cu-catalyzed regioselective and stereospecific aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines that delivers the corresponding beta-aminoalkylboranes in good yields has been developed. The Cu catalysis enables introduction of both amine and boron moieties to C-C double bonds simultaneously in a syn fashion. Moreover, the use of a chiral biphosphine ligand, (S,S)-Me-Duphos, provides a catalytic enantioselective route to optically active beta-aminoalkylboranes.

  DOI：

  10.1021/ja4007645
• 作为产物：
  描述：

  甲基苯乙烯 、 N,N-dibenzyl-O-benzoylhydroxylamine 、 联硼酸频那醇酯 在 (+)-1,2-双((2S,5S)-2,5-二甲基磷烷)苯 、 copper(l) chloride 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以72%的产率得到N,N-dibenzyl-1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-amine
  参考文献：
  名称：

  Regioselective and Stereospecific Copper-Catalyzed Aminoboration of Styrenes with Bis(pinacolato)diboron and O-Benzoyl-N,N-dialkylhydroxylamines

  摘要：

  A Cu-catalyzed regioselective and stereospecific aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines that delivers the corresponding beta-aminoalkylboranes in good yields has been developed. The Cu catalysis enables introduction of both amine and boron moieties to C-C double bonds simultaneously in a syn fashion. Moreover, the use of a chiral biphosphine ligand, (S,S)-Me-Duphos, provides a catalytic enantioselective route to optically active beta-aminoalkylboranes.

  DOI：

  10.1021/ja4007645

文献信息

• Cu-Catalyzed Asymmetric Aminoboration of <i>E</i>-Vinylarenes with ^<i>piv</i>ZPhos as the Ligand
  作者：Linglin Wu、Olga Zatolochnaya、Bo Qu、Ling Wu、Lucille A. Wells、Marisa C. Kozlowski、Chris H. Senanayake、Jinhua J. Song、Yongda Zhang

  DOI：10.1021/acs.orglett.9b03328

  日期：2019.11.15

  enantioselectivities up to >99:1 er under the optimized conditions. The utility of the current method was further established by rapid conversion of an adduct to a chiral benzo[f][1,4]oxazepine. A model for the stereochemistry of the asymmetric aminoboration process, which agrees with the experimental outcomes, was generated by computational analysis of the systems.

  报道了具有piv ZPhos作为配体的Cu催化的E-乙烯基芳烃的对映选择性氨基硼化。在优化的条件下，制备的对映体富集的氨基硼酸盐具有高达> 99：1的极佳区域选择性和对映体选择性。通过将加合物快速转化为手性苯并[ f ] [1,4]奥氮平，进一步建立了当前方法的实用性。通过系统的计算分析，生成了与实验结果相符的不对称氨基硼酸酯化过程立体化学模型。