(aR,1'S)-N,N-diisopropyl-2-(1'-hydroxyethyl)-1-naphthamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (aR,1'S)-N,N-diisopropyl-2-(1'-hydroxyethyl)-1-naphthamide
• 英文别名: 2-[(1S)-1-hydroxyethyl]-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: OZASEBOEXZDWEJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (aR,1'S)-N,N-diisopropyl-2-(1'-hydroxyethyl)-1-naphthamide 在 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 8.0h， 生成 (-)-(aR,1'S,1''R,2''S)-N,N-diisopropyl-2-[1'-(2''-methoxycarbonylcycloxex-4''-ene-1''-carbonyloxy)ethyl]-1-naphthamide
  参考文献：
  名称：

  Study on enantiomerically pure 2-substituted N,N-dialkyl-1-naphthamides: resolution, absolute stereochemistry, and application to desymmetrization of cyclic meso anhydrides

  摘要：

  The axially chiral 2-substituted N,N-diisoproyl-1-1-naphthamides 1 and 2 were resolved by HPLC over a chiral stationary phase to provide enantiomerically pure atropisomers. The absolute stereochemistry of was determined by X-ray crystallographic analysis of the corresponding (1S)-camphanic acid derivative. Desymmetrization of cyclic meso anhydrides 5a and 5b using (-)-syn-1 gave a single diastercomer in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00278-6
• 作为产物：
  描述：

  N,N-diisopropyl-2-ethyl-1-naphthamide 在 过氧乙酸 、 mercury(II) diacetate 、 仲丁基锂 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 (aR,1'S)-N,N-diisopropyl-2-(1'-hydroxyethyl)-1-naphthamide
  参考文献：
  名称：

  Atroposelectivity in the Reactions of Laterally Lithiated Tertiary Amides

  摘要：

  Lateral lithiation-electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation-alkylation reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00401-2

文献信息

• Asymmetric induction using atropisomers: Diastereoselective additions to 2-acyl-1-naphthamides
  作者：Jonathan Clayden、Neii Westlund、Francis X Wilson

  DOI：10.1016/0040-4039(96)01129-x

  日期：1996.7

  The amide group of 2-acyl-N,N-dialkyl-1-naphthamides, twisted perpendicular to the naphthyl ring, controls the stereoselectivity of attack of nucleophiles on the 2-substituent. Selectivities of >140:1 may be achieved with bulky nucleophiles, which attack anti to the N,N-dialkyl group.

  垂直于萘基环扭曲的2-酰基-N，N-二烷基-1-萘酰胺的酰胺基控制亲核试剂攻击2-取代基的立体选择性。的> 140选择性：1可与亲核试剂笨重，其攻击来实现抗到Ñ，Ñ二烷基团。
• Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes
  作者：Peter Bowles、Jonathan Clayden、Matthew Tomkinson

  DOI：10.1016/0040-4039(95)01945-e

  日期：1995.12

  2-Substituted N,N-diethyl or N,N-diisopropyl 1-naphthamides exist as stable atropisomers. When the 2-substituent is a 1-hydroxyalkyl group, the atropisomers are separable diastereoisomers. Synthesis of these compounds by the addition of aldehydes to ortholithiated N,N-dialkyl 1-naphthamides proceeds with moderate to good diastereoselectivity in favour of the aR*S* (syn) diastereoisomer.