(4S,10R,11R)-4-hydroxy-10-methyl-11-((tetrahydropyran-2-yl)oxy)dodec-2-en-1,4-olide | 1206551-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (4S,10R,11R)-4-hydroxy-10-methyl-11-((tetrahydropyran-2-yl)oxy)dodec-2-en-1,4-olide
• 英文别名: (2S)-2-[(6R,7R)-6-methyl-7-(oxan-2-yloxy)octyl]-2H-furan-5-one
• CAS: 1206551-70-3
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: IWDLLHOWBPGOSV-LTBNCBHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,10R,11R)-4-hydroxy-10-methyl-11-((tetrahydropyran-2-yl)oxy)dodec-2-en-1,4-olide 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到(4S,10R,11R)-4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115
• 作为产物：
  描述：

  (3S,9R,10R)-9-methyl-10-((tetrahydropyran-2-yl)oxy)undec-1-en-3-yl acrylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到(4S,10R,11R)-4-hydroxy-10-methyl-11-((tetrahydropyran-2-yl)oxy)dodec-2-en-1,4-olide
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115

文献信息

• Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone
  作者：Yan Wang、Wei-Min Dai

  DOI：10.1016/j.tet.2009.10.115

  日期：2010.1

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.