(2E,8E,10E)-Dodeca-2,8,10-trienoic acid methoxy-phenyl-amide | 550346-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,8E,10E)-Dodeca-2,8,10-trienoic acid methoxy-phenyl-amide
• 英文别名: (2E,8E,10E)-N-methoxy-N-phenyldodeca-2,8,10-trienamide
• CAS: 550346-98-0
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: WLZPQJMJQRUFGP-NJVZWDTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  (2E,8E,10E)-Dodeca-2,8,10-trienoic acid methoxy-phenyl-amide 以 甲苯 为溶剂， 反应 144.0h， 生成 (1S,2R,4aS,8aS)-2-Methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methoxy-phenyl-amide 、 (1S,2S,4aR,8aS)-2-Methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methoxy-phenyl-amide
  参考文献：
  名称：

  Synthesis of (±)-solanapyrones A and B

  摘要：

  In this paper we report the development of a stereoselective IMDA approach to the phytotoxic polyketides (+/-)-solanapyrones A and B. The stereoselectivity of the key IMDA cycloaddition was optimized by investigating a range of 2,8,10-dodecatrienoic acid derivatives. This established that use of the Weinreb amide led to the desired exo-selectivity and also facilitated construction of the pyrone moiety. A novel approach to the installation of the C-3 formyl group in solanapyrone A is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00288-0
• 作为产物：
  描述：

  (2E,8E,10E)-dodeca-2,8,10-trienoic acid 在 草酰氯 、 碳酸氢钠 、 potassium carbonate 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2E,8E,10E)-Dodeca-2,8,10-trienoic acid methoxy-phenyl-amide
  参考文献：
  名称：

  Synthesis of (±)-solanapyrones A and B

  摘要：

  In this paper we report the development of a stereoselective IMDA approach to the phytotoxic polyketides (+/-)-solanapyrones A and B. The stereoselectivity of the key IMDA cycloaddition was optimized by investigating a range of 2,8,10-dodecatrienoic acid derivatives. This established that use of the Weinreb amide led to the desired exo-selectivity and also facilitated construction of the pyrone moiety. A novel approach to the installation of the C-3 formyl group in solanapyrone A is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00288-0

文献信息

• Synthesis of (±)-solanapyrones A and B
  作者：Barry Lygo、Mohamed Bhatia、Jason W.B. Cooke、David J. Hirst

  DOI：10.1016/s0040-4039(03)00288-0

  日期：2003.3

  In this paper we report the development of a stereoselective IMDA approach to the phytotoxic polyketides (+/-)-solanapyrones A and B. The stereoselectivity of the key IMDA cycloaddition was optimized by investigating a range of 2,8,10-dodecatrienoic acid derivatives. This established that use of the Weinreb amide led to the desired exo-selectivity and also facilitated construction of the pyrone moiety. A novel approach to the installation of the C-3 formyl group in solanapyrone A is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.