(2R,4S)-5-azido-2,4-dimethylpentanal | 335060-57-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2R,4S)-5-azido-2,4-dimethylpentanal
• CAS: 335060-57-6
• 化学式: C₇H₁₃N₃O
• 分子量: 155.2
• InChiKey: NEXYANZMUQUMJK-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S)-5-azido-2,4-dimethylpentanal 在 potassium cyanide 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids

  摘要：

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02157-2
• 作为产物：
  描述：

  (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol 在 叠氮磷酸二苯酯 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,4S)-5-azido-2,4-dimethylpentanal
  参考文献：
  名称：

  Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids

  摘要：

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02157-2

文献信息

• Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids
  作者：Junliang Hao、Josep Aiguade、Craig J Forsyth

  DOI：10.1016/s0040-4039(00)02157-2

  日期：2001.1

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.