((2S,2'S,5R,5'R)-5'-((S)-1-hydroxyundec-2-yn-1-yl)octahydro-[2,2'-bifuran]-5-yl)methyl benzoate | 1086569-65-4

• 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: ((2S,2'S,5R,5'R)-5'-((S)-1-hydroxyundec-2-yn-1-yl)octahydro-[2,2'-bifuran]-5-yl)methyl benzoate
• CAS: 1086569-65-4
• 化学式: C₂₇H₃₈O₅
• 分子量: 442.596
• InChiKey: WFKFMVDOYVPEPM-NRWDCXGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((2S,2'S,5R,5'R)-5'-((S)-1-hydroxyundec-2-yn-1-yl)octahydro-[2,2'-bifuran]-5-yl)methyl benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 生成 [(2R,5S)-5-[(2S,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Alteration of the Bis-tetrahydrofuran Core Stereochemistries in Asimicin Can Affect the Cytotoxicity

  摘要：

  A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.

  DOI：

  10.1021/jm801028c
• 作为产物：
  描述：

  1-癸炔 、 [(2R,5S)-5-[(2S,5R)-5-formyloxolan-2-yl]oxolan-2-yl]methyl benzoate 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以52%的产率得到((2S,2'S,5R,5'R)-5'-((R)-1-hydroxyundec-2-yn-1-yl)octahydro-[2,2'-bifuran]-5-yl)methyl benzoate
  参考文献：
  名称：

  Alteration of the Bis-tetrahydrofuran Core Stereochemistries in Asimicin Can Affect the Cytotoxicity

  摘要：

  A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.

  DOI：

  10.1021/jm801028c