N,N-diisopropyl-8-hydroxy-1-naphthamide | 252270-69-2

• 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-hydroxy-1-naphthamide
• 英文别名: 8-hydroxy-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 252270-69-2
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: OYHMGWFPHHTTSP-UHFFFAOYSA-N

物化性质

• 沸点：
  452.4±18.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-8-hydroxy-1-naphthamide 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 53.67h， 生成
  参考文献：
  名称：

  Synthesis and properties of atropisomeric phosphinous acids

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.01.093
• 作为产物：
  描述：

  8-[(diisopropylamino)carbonyl]-1-naphthyl propionate 在 lithium diisopropyl amide 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以25%的产率得到N,N-diisopropyl-8-hydroxy-1-naphthamide
  参考文献：
  名称：

  阻转异构的苯甲酰胺和萘酰胺作为手性助剂

  摘要：

  手性位于旋转受限的阻转异构化合物 芳基–CONR 2键可用作手性助剂。吸电子酰胺基团导致由对映异构苯基酯衍生的烯醇酯的非对映选择性官能化产生问题，但是基于将对映异构性亲核加成到手性化合物上的策略醛随后进行立体定向[3,3]σ重排，可以将阻转异构萘酰胺用作助剂。辅助通过动态分辨率解决阿米纳尔 脯氨酸衍生形成 二胺。

  DOI：

  10.1039/b004682p

文献信息

• A Novel Class of Nonbiaryl Atropisomeric P,O-Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylation
  作者：Wei-Min Dai、Kelly Ka Yim Yeung、Jin-Teng Liu、Ye Zhang、Ian D. Williams

  DOI：10.1021/ol0258233

  日期：2002.5.1

  [structure: see text]. A novel class of nonbiaryl atropisomeric P,O-ligands possessing an N,N-dialkyl-1-naphthamide skeleton has been synthesized via an efficient chemical resolution process. It represents the first example of axially chiral P,O-ligands devoid of central chirality. Up to 94.7% ee was obtained for the Pd-catalyzed asymmetric allylic alkylation (AAA). Effects of solvent, base, and the

  [结构：见文字]。通过有效的化学拆分过程合成了具有N，N-二烷基-1-萘酰胺骨架的新型一类非联芳基阻转异构体P，O-配体。它代表了没有中心手性的轴向手性P，O-配体的第一个例子。对于Pd催化的不对称烯丙基烷基化（AAA），可获得高达94.7％的ee。检查了溶剂，碱和P，O-配体的C8氧基团的体积对AAA反应的影响。
• 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.
• Perilithiation and the synthesis of 8-substituted-1-naphthamides
  作者：Jonathan Clayden、Christopher S. Frampton、Catherine McCarthy、Neil Westlund

  DOI：10.1016/s0040-4020(99)00881-9

  日期：1999.12

  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.
• Atropisomeric benzamides and naphthamides as chiral auxiliaries †
  作者：Jonathan Clayden、Madeleine Helliwell、Catherine McCarthy、Neil Westlund

  DOI：10.1039/b004682p

  日期：——

  The electron-withdrawing amide group causes problems in the diastereoselective functionalisation of enolates derived from atropisomeric phenyl esters, but a strategy based on atroposelective nucleophilic addition to a chiral aldehyde followed by stereospecific [3,3] sigmatropic rearrangement allows atropisomeric naphthamides to be used as auxiliaries. The auxiliaries are resolved by dynamic resolution

  手性位于旋转受限的阻转异构化合物 芳基–CONR 2键可用作手性助剂。吸电子酰胺基团导致由对映异构苯基酯衍生的烯醇酯的非对映选择性官能化产生问题，但是基于将对映异构性亲核加成到手性化合物上的策略醛随后进行立体定向[3,3]σ重排，可以将阻转异构萘酰胺用作助剂。辅助通过动态分辨率解决阿米纳尔 脯氨酸衍生形成 二胺。
• 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.