N,N-diisopropyl-2-hydroxy-8-methoxy-1-naphthamide | 676613-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diisopropyl-2-hydroxy-8-methoxy-1-naphthamide
• 英文别名: 2-hydroxy-N,N-diisopropyl-8-methoxy-1-naphthamide；2-hydroxy-8-methoxy-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 676613-74-4
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: WXGAUTMROJXLCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-2-hydroxy-8-methoxy-1-naphthamide 在 AD-mix-β 、 potassium hexacyanoferrate(III) (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan] 、 potassium osmate(VI) 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 2,3-Dihydroxy-butyric acid 1-diisopropylcarbamoyl-8-methoxy-naphthalen-2-yl ester
  参考文献：
  名称：

  Synthesis of atropisomeric 2,8-dioxygenated N,N-diisopropyl-1-naphthamides via kinetic resolution under Sharpless asymmetric dihydroxylation conditions

  摘要：

  A kinetic resolution approach under Sharpless asymmetric dihydroxylation conditions was used to synthesize enantio-enriched atropisomeric N,N-diisopropyl-1-naphthamides possessing oxygenated functionalities at both the C2 and C8 positions. A significant influence of the substrate structures on the efficiency of the kinetic resolution was observed. (+)-(aS)-N,N-Diisopropyl-2[2'-(E)-butenoyloxy]-8-methoxy-1-naphthamide is obtained in 35% yield with 94.3% ee after treating the racemate with 3.5 mol% each of Os and (DHQD)(2)-PHAL at 0degreesC for 22 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.039
• 作为产物：
  描述：

  N,N-diisopropyl-8-hydroxy-1-naphthamide 在 仲丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 27.0h， 生成 N,N-diisopropyl-2-hydroxy-8-methoxy-1-naphthamide
  参考文献：
  名称：

  Synthesis of atropisomeric 2,8-dioxygenated N,N-diisopropyl-1-naphthamides via kinetic resolution under Sharpless asymmetric dihydroxylation conditions

  摘要：

  A kinetic resolution approach under Sharpless asymmetric dihydroxylation conditions was used to synthesize enantio-enriched atropisomeric N,N-diisopropyl-1-naphthamides possessing oxygenated functionalities at both the C2 and C8 positions. A significant influence of the substrate structures on the efficiency of the kinetic resolution was observed. (+)-(aS)-N,N-Diisopropyl-2[2'-(E)-butenoyloxy]-8-methoxy-1-naphthamide is obtained in 35% yield with 94.3% ee after treating the racemate with 3.5 mol% each of Os and (DHQD)(2)-PHAL at 0degreesC for 22 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.039

文献信息

• Dynamic Kinetic Resolution of Axially Chiral Naphthamides via Atroposelective Allylic Alkylation Reaction
  作者：Shou-Lei Li、Quan Wu、Chen Yang、Xin Li、Jin-Pei Cheng

  DOI：10.1021/acs.orglett.9b01796

  日期：2019.7.19

  Axially chiral amides are usually found in many biologically active compounds and are useful ligands in asymmetric catalysis. Herein, by using the dynamic kinetic resolution approach, an asymmetric allylic alkylation reaction of racemic amide naphthols is disclosed, which leads to generation of the axially chiral naphthamides in good to excellent yields (up to 97%) and enantioselectivities (up to 96:4

  轴向手性酰胺通常存在于许多生物活性化合物中，并且在不对称催化中是有用的配体。本文中，通过使用动态动力学拆分方法，揭示了外消旋酰胺萘的不对称烯丙基烷基化反应，其导致轴向手性萘酰胺的生成，具有良好的产率（高达97％）和对映选择性（高达96：4）。 er）。使用密度泛函理论来获得对该反应中对映选择性的理论理解。
• Hydrogen‐Bond‐Enabled Dynamic Kinetic Resolution of Axially Chiral Amides Mediated by a Chiral Counterion
  作者：Alison J. Fugard、Antti S. K. Lahdenperä、Jaqueline S. J. Tan、Aroonroj Mekareeya、Robert S. Paton、Martin D. Smith

  DOI：10.1002/anie.201814362

  日期：2019.2.25

  their enantioselective synthesis remains a challenge. Herein, a counterion‐mediated O‐alkylation method for the generation of atropisomeric amides with an er up to 99:1 is outlined. This dynamic kinetic resolution is enabled by the observation that the rate of racemization of atropisomeric naphthamides is significantly increased by the presence of an intramolecular O−H⋅⋅⋅NCO hydrogen bond. Upon O‐alkylation

  非联芳基阻转异构体在医学、材料和催化方面具有重要价值，但其对映选择性合成仍然是一个挑战。本文概述了一种抗衡离子介导的 O-烷基化方法，用于生成 er 高达 99:1 的阻转异构酰胺。这种动态动力学分辨率是通过观察到由于分子内 OH⋅⋅⋅NCO 氢键的存在而显着增加了阻转异构萘酰胺的外消旋化速率而实现的。当氢键供体发生 O 烷基化时，旋转势垒显着增加。量子计算表明，分子内氢键减少了芳基酰胺键的旋转势垒，使外消旋化的平面过渡态稳定约 40 kJ mol -1，从而促进了观察到的动态动力学分辨率。