N,N-diisopropyl-2-formyl-8-methoxy-1-naphthamide | 252270-71-6

• 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-formyl-8-methoxy-1-naphthamide
• 英文别名: 2-formyl-8-methoxy-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 252270-71-6；252288-93-0；252288-96-3
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: YXJGOSIFOLQFOG-UHFFFAOYSA-N

物化性质

• 沸点：
  498.0±30.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-2-formyl-8-methoxy-1-naphthamide 在 盐酸 、 Lindlar's catalyst 、 正丁基锂 、 丙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 xylene 、 正丁醇 为溶剂， -78.0~140.0 ℃ 、101.33 kPa 条件下， 反应 120.5h， 生成 (3'R)-N,N-diisopropyl-2-[(E)-3'-(N,N-dimethylcarbamoylmethyl)non-1'-enyl]-8-methoxy-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
• 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 26.0h， 生成 N,N-diisopropyl-2-formyl-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

• Efficient Remote Axial-to-Central Chirality Transfer in Enantioselective SmI₂-Mediated Reductive Coupling of Aldehydes with Crotonates of Atropisomeric 1-Naphthamides
  作者：Yan Zhang、Yongqiang Wang、Wei-Min Dai

  DOI：10.1021/jo0526486

  日期：2006.3.1

  different 2-substituted 8-methoxy-1-naphthamides. The enantiomers of atropisomeric 8-methoxy-1-naphthamides were prepared through a chemical resolution process, and their absolute stereochemistry was determined by X-ray crystal structural analysis. It was found that the linkage between crotonate and the C2 position of 8-methoxy-1-naphthamides remarkably influenced the efficiency of remote chirality transfer

  在SmI 2介导的醛与具有不同的2-取代的8-甲氧基-1-萘酰胺的巴豆酸酯的还原偶联中，已经研究了通过远程酰胺构象控制对映选择性的方法。通过化学拆分方法制备对映异构体8-对甲氧基-1-萘酰胺的对映异构体，并通过X射线晶体结构分析确定其绝对立体化学。发现巴豆酸酯和8-甲氧基-1-萘酰胺的C2位之间的键合显着影响源自酰胺构象的远程手性转移的效率。在所检查的四种巴豆酸酯中，一种由2-羟基-8-甲氧基-1-萘酰胺衍生的戊烯酸酯与戊醛反应，以使顺式的ee最高，> 99％-γ-丁内酯，合并产率为90％，顺/反比为90:10。我们开发了一种在温和条件下通过C8氧将手性巴豆酸酯连接到Rink酰胺树脂上的新程序，并在固相反应中获得了相同水平的极远的轴向向中心手性转移。
• Dynamically resolved peri-substituted 2-formyl naphthamides: a new class of atropisomeric chiral auxiliary
  作者：Jonathan Clayden、Catherine McCarthy、John G Cumming

  DOI：10.1016/s0040-4039(00)00397-x

  日期：2000.4

  the amide group. They may be obtained as single enantiomers by dynamic resolution on formation of diastereoisomeric aminal derivatives and used as chiral auxiliaries in a new addition/rearrangement strategy. Nucleophilic attack by vinyl anion equivalents in the presence of Lewis acids leads atroposelectively to single diastereoisomers of allylic alcohols, whose derivatives undergo stereospecific [3

  2-甲酰基-N，N-二烷基萘酰胺是手性的阻转异构化合物，只要它们在酰胺基团周围被取代即可。它们可以通过动态拆分非对映异构的氨基衍生物的形成而作为单一对映异构体获得，并在新的添加/重排策略中用作手性助剂。在路易斯酸的存在下，乙烯基阴离子当量的亲核攻击会导致对映体选择性地导致烯丙基醇的单一非对映异构体，其衍生物会经历立体有规[3,3]-σ重排。重排产物的还原性臭氧分解返回对映体纯的官能化醇，并且原则上可以回收阻转异构体助剂。
• (−)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control
  作者：Jonathan Clayden、Lai Wah Lai

  DOI：10.1016/s0040-4039(01)00416-6

  日期：2001.4

  N,N-Dialkyl-2-formylbenzamides and N,N-dialkyl-2-formyl-1-naphthamides condense with (-)-ephedrine in refluxing toluene to give oxazolidines both as single diastereoisomers with respect to the new stereogenic centre and as single conformers with respect to the slowly-rotating Ar-CONR2 bond. In the naphthamide series, removal of the ephedrine auxiliary by hydrolysis returns the starting aldehyde (isolated by reduction to the more stable alcohol) in enantiomerically enriched form (up to 94% ee). Overall, the two-step sequence amounts to a dynamic resolution under thermodynamic control. (C) 2001 Elsevier Science 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。