(-)-(aS,1'S,1''R,2''S)-N,N-diisopropyl-2-[1'-(2''-methoxycarbonylcycloxex-4''-ene-1''-carbonyloxy)ethyl]-1-naphthamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-(aS,1'S,1''R,2''S)-N,N-diisopropyl-2-[1'-(2''-methoxycarbonylcycloxex-4''-ene-1''-carbonyloxy)ethyl]-1-naphthamide
• 英文别名: 2-O-[(1S)-1-[1-[di(propan-2-yl)carbamoyl]naphthalen-2-yl]ethyl] 1-O-methyl (1S,2R)-cyclohex-4-ene-1,2-dicarboxylate
• 化学式: C₂₈H₃₅NO₅
• 分子量: 465.59
• InChiKey: BQPWTQQUJADWNN-WDJPJFJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-diisopropyl-2-formyl-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 11.0h， 生成 (-)-(aS,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

文献信息

• Study on enantiomerically pure 2-substituted N,N-dialkyl-1-naphthamides: resolution, absolute stereochemistry, and application to desymmetrization of cyclic meso anhydrides
  作者：Wei-Min Dai、Kelly Ka Yim Yeung、Chun Wo Chow、Ian D. Williams

  DOI：10.1016/s0957-4166(01)00278-6

  日期：2001.7

  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.