prop-2-enyl (2E,4E,6E)-9-azidonona-2,4,6-trienoate | 919771-02-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: prop-2-enyl (2E,4E,6E)-9-azidonona-2,4,6-trienoate
• CAS: 919771-02-1
• 化学式: C₁₂H₁₅N₃O₂
• 分子量: 233.27
• InChiKey: AILDCNYWTQXUJE-GJOOXVBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2E,4E,6E)-9-azidonona-2,4,6-trienoate 在 四(三苯基膦)钯 水 、 二乙胺 、 三苯基膦 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  A flexible route to immunosuppressive agent FR252921. Asymmetric total synthesis of its (13R,14R,19R)-isomer

  摘要：

  A flexible route to the proposed structure of FR252921, a novel immunosuppressive agent, is developed. The key elements include the assembly of its two P-hydroxy acid residues via asymmetric aldol condensation of N-acylthiazolidinethinones with aldehydes, and its triene part via a CuI/N,N-dimethylglycine catalyzed Sonogashira coupling and subsequent isomerization. Using this strategy (13R,14R,19R)-FR252921 is elaborated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.169
• 作为产物：
  描述：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 copper(l) iodide 4-二甲氨基吡啶 、 sodium azide 、 N,N-二甲基甘氨酸 、 四丁基氟化铵 、 caesium carbonate 、 三乙胺 、 三苯基膦 、 苯酚 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 prop-2-enyl (2E,4E,6E)-9-azidonona-2,4,6-trienoate
  参考文献：
  名称：

  A flexible route to immunosuppressive agent FR252921. Asymmetric total synthesis of its (13R,14R,19R)-isomer

  摘要：

  A flexible route to the proposed structure of FR252921, a novel immunosuppressive agent, is developed. The key elements include the assembly of its two P-hydroxy acid residues via asymmetric aldol condensation of N-acylthiazolidinethinones with aldehydes, and its triene part via a CuI/N,N-dimethylglycine catalyzed Sonogashira coupling and subsequent isomerization. Using this strategy (13R,14R,19R)-FR252921 is elaborated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.169

文献信息

• A flexible route to immunosuppressive agent FR252921. Asymmetric total synthesis of its (13R,14R,19R)-isomer
  作者：Shouyun Yu、Feng Liu、Dawei Ma

  DOI：10.1016/j.tetlet.2006.09.169

  日期：2006.12

  A flexible route to the proposed structure of FR252921, a novel immunosuppressive agent, is developed. The key elements include the assembly of its two P-hydroxy acid residues via asymmetric aldol condensation of N-acylthiazolidinethinones with aldehydes, and its triene part via a CuI/N,N-dimethylglycine catalyzed Sonogashira coupling and subsequent isomerization. Using this strategy (13R,14R,19R)-FR252921 is elaborated. (c) 2006 Elsevier Ltd. All rights reserved.