P-1-(4',6'-dimethyl-2'-hydroxyphenyl)-2-(N,N-di-n-butylaminomethyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: P-1-(4',6'-dimethyl-2'-hydroxyphenyl)-2-(N,N-di-n-butylaminomethyl)naphthalene
• 英文别名: 1-(4',6'-dimethyl-2'-hydroxyphenyl)-2-(N,N-di-n-butylaminomethyl)naphthalene；2-[2-[(Dibutylamino)methyl]naphthalen-1-yl]-3,5-dimethylphenol
• 化学式: C₂₇H₃₅NO
• 分子量: 389.581
• InChiKey: ACNMJTIKZNCJHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-(hydroxymethyl)naphthalen-1-yl)-3,5-dimethylphenol 在 lithium aluminium tetrahydride 、 三氯化硼 、 N-甲基-N-苯胺基三苯基碘化膦 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 13.67h， 生成 P-1-(4',6'-dimethyl-2'-hydroxyphenyl)-2-(N,N-di-n-butylaminomethyl)naphthalene
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts [1]

  摘要：

  The synthesis of atropo-enantiomerically pure aminomethyl and hydroxymethyl substituted biaryls derivatives M-2 and M-3 (and, optionally, their enantiomers), by dynamic kinetic resolution of a racemic lactone precursor, is described. Their application as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes leads to excellent enantiomeric ratios of up to 99:1 and high chemical yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00020-2
• 作为试剂：
  描述：

  diethylzinc 、 1-萘甲醛 在 P-1-(4',6'-dimethyl-2'-hydroxyphenyl)-2-(N,N-di-n-butylaminomethyl)naphthalene 作用下， 以 正己烷 为溶剂， 反应 16.0h， 生成 (S)-1-naphthalen-1-yl-propan-1-ol
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts [1]

  摘要：

  The synthesis of atropo-enantiomerically pure aminomethyl and hydroxymethyl substituted biaryls derivatives M-2 and M-3 (and, optionally, their enantiomers), by dynamic kinetic resolution of a racemic lactone precursor, is described. Their application as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes leads to excellent enantiomeric ratios of up to 99:1 and high chemical yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00020-2

文献信息

• Ruthenium-Catalyzed Atropoenantioselective Synthesis of Axial Biaryls via Reductive Amination and Dynamic Kinetic Resolution
  作者：Donghui Guo、Jianwei Zhang、Bei Zhang、Jian Wang

  DOI：10.1021/acs.orglett.8b02785

  日期：2018.10.5

  via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in good to high yields with high to excellent enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral

  描述了通过级联转移氢化和动态动力学拆分策略，空前的钌催化的烷基胺对醛的对苯二酸选择性还原胺化反应。该方案具有广泛的底物范围和良好的官能团耐受性，并允许以高至高收率和高至优异的对映选择性快速组装轴向手性联芳基。另外，这样的结构基序可以作为手性配体或催化剂在对映选择性催化中具有潜在的应用。