N,N-diisopropyl-8-methoxy-1-naphthamide | 252270-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diisopropyl-8-methoxy-1-naphthamide
• 英文别名: 8-methoxy-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 252270-68-1；252288-85-0；252288-87-2；722455-86-9
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: PRKLFXOGFFSMFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-8-methoxy-1-naphthamide 在 仲丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N,N-diisopropyl-2-[2'-(E)-butenyloxy]-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
• 作为产物：
  描述：

  2H-萘并[1,8-bc]呋喃-2-酮 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 28.33h， 生成 N,N-diisopropyl-8-methoxy-1-naphthamide
  参考文献：
  名称：

  Perilithiation and the synthesis of 8-substituted-1-naphthamides

  摘要：

  Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing l-substituents such as -NMe2 or -CH2NMe2 allows the synthesis of 8-substituted-1-naphthamides. The 8-CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00881-9

文献信息

• Sulfoxides as ‘traceless’ resolving agents for the synthesis of atropisomers by dynamic or classical resolution
  作者：Jonathan Clayden、Przemyslaw M Kubinski、Federica Sammiceli、Madeleine Helliwell、Louis Diorazio

  DOI：10.1016/j.tet.2004.01.099

  日期：2004.5

  stereochemical integrity. Overall the reaction sequence is a resolution but without the need for an acidic or basic substituent—a ‘traceless’ method. In certain instances, for example when the nucleophile is an ortholithiated peri-substituted 1-naphthamide, the diastereoisomeric sulfoxides may be interconverted thermally. This allows a dynamic resolution, under thermodynamic control, and hence in principle

  （-）-薄荷基亚磺酸盐与阻转异构但外消旋的芳基锂反应生成两种阻转非对映异构亚砜。每种非对映异构体的分离（通过色谱法或结晶法）和亚砜-锂交换可再生出对映体纯形式的芳基锂，可以用一系列亲电试剂将其淬灭，并保留立体化学完整性。总的来说，反应顺序是分离的，但不需要酸性或碱性取代基-“无痕”方法。在某些情况下，例如，当亲核试剂为ortholithiated迫取代的1-萘酰胺可以将非对映异构亚砜热转化。这允许在热力学控制下进行动态拆分，因此原则上可以使最终产物的产率大于50％。通过合成已知的阻转异构膦配体证明了该方法的实用性。
• Determination of absolute configuration of 2-methyl-1-(o-tolyl)naphthalene and the related axially chiral biaryls
  作者：Lijie Sun、Wei-Min Dai

  DOI：10.1016/j.tet.2011.09.107

  日期：2011.11

  (aS)-2-methyl-1-[(((o-triisopropylsilyl)oxy)methyl)phenyl]naphthalene was produced via catalytic asymmetric Suzuki–Miyaura cross-coupling using an atropisomeric naphthamide-derived phosphine (A2phos) as the chiral ligand. After one recrystallization, enantiopurity of the biaryl product was improved to 98.9% ee and its absolute configuration was determined by X-ray crystal structural analysis. Through chemical transformations

  通过使用不对称异构体的催化不对称Suzuki-Miyaura交叉偶联反应制备了对映体富集的（a S）-2-甲基-1-[（（（（o-三异丙丙基甲硅烷基）氧基）甲基）苯基]萘的对映体样品（84.3％ee）萘酰胺衍生的膦（A 2 phos）作为手性配体。重结晶一次后，联芳基产物的对映体纯度提高至ee的98.9％，并通过X射线晶体结构分析确定其绝对构型。通过化学转化中，（一个小号[（ - ）1 -对映体的直径：羟甲基）苯基] -2-甲基萘，1 - [（ø氯甲基）苯基] -2-甲基萘，2-甲基-1-（Ø获得了甲苯基萘。合成了其他几种手性联芳基，并进行了立体化学分配。
• Synthesis and properties of atropisomeric phosphinous acids
  作者：Paul Wyatt、Peter Hooper、Francine Sternfeld

  DOI：10.1016/j.tet.2004.01.093

  日期：2004.5

  In this paper we describe two groups of atropisomeric phosphinous acids-bis-[(N,N-diisopropyl-1-naphthamide)-2-]-phosphinous acids (2 to 4) and their 8-methoxy- substituted relations (8 to 10). The first group of acids interconvert at room temperature and the second group do not. The interconversion and properties are illustrated by two dimensional TLC and some NMR spectra. The peri substituent turns out to be important. (C) 2004 Elsevier Ltd. All rights reserved.
• The first example of atropisomeric amide-derived P,O-ligands used for an asymmetric Heck reaction
  作者：Wei-Min Dai、Kelly Ka Yim Yeung、Yongqiang Wang

  DOI：10.1016/j.tet.2004.02.062

  日期：2004.5

  Atropisomeric N,N-diisopropyl 2-diphenylphosphino- and 2-di(tert-butyl)phosphino-1-naphthamides were used, for the first time, as bidentate P,O-ligands for intermolecular asymmetric Heck reactions of 2,3-dihydrofuran with aryl triflates. The reactions were carried out in the presence of 4 mol% Pd(OAc)(2), 8 mol% of the axially chiral ligand, and 3 equiv. of (i-Pr)(2)NEt in THF at 60 degreesC for 3 days. Optically active 2-aryl-2,5-dihydrofurans were obtained as the major products along with the rearranged 2-aryl-2,3-dihydrofurans. Enantioselectivity up to 55.2% ee was obtained for the major product. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of atropisomeric 2,8-dioxygenated N,N-diisopropyl-1-naphthamides via kinetic resolution under Sharpless asymmetric dihydroxylation conditions
  作者：Wei-Min Dai、Yan Zhang、Ye Zhang

  DOI：10.1016/j.tetasy.2003.11.039

  日期：2004.2

  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.