3-dodec-11-enyl-(5S)-methyl-3-phenylsulfanyl-dihydrofuran-2-one | 943024-25-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-dodec-11-enyl-(5S)-methyl-3-phenylsulfanyl-dihydrofuran-2-one
• 英文别名: (5S)-3-dodec-11-enyl-5-methyl-3-phenylsulfanyloxolan-2-one
• CAS: 943024-25-7
• 化学式: C₂₃H₃₄O₂S
• 分子量: 374.588
• InChiKey: KGBRAOUNPZGHIQ-AJZOCDQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-dodec-11-enyl-(5S)-methyl-3-phenylsulfanyl-dihydrofuran-2-one 、 acrylic acid (2R)-benzyloxy-(1R)-vinylbut-3-enyl ester 在 Hoveyda-Grubbs' second-generation catalyst 作用下， 以 苯 为溶剂， 反应 14.0h， 以77%的产率得到(5R)-[(1R)-benzyloxy-13-[(5S)-methyl-2-oxo-3-phenylsulfanyltetrahydrofuran-3-yl]-tridec-2-enyl]-5H-furan-2-one
  参考文献：
  名称：

  Convergent total synthesis of squamostolide

  摘要：

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.151
• 作为产物：
  描述：

  10-十一烯醛 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 mercury(II) diacetate 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.17h， 生成 3-dodec-11-enyl-(5S)-methyl-3-phenylsulfanyl-dihydrofuran-2-one
  参考文献：
  名称：

  Convergent total synthesis of squamostolide

  摘要：

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.151

文献信息

• Convergent total synthesis of squamostolide
  作者：Kevin J. Quinn、Austin G. Smith、Carolyn M. Cammarano

  DOI：10.1016/j.tet.2007.03.151

  日期：2007.6

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.