(1R,2S,6S,9S)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-7-en-2-ol | 1305340-00-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,6S,9S)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-7-en-2-ol
• CAS: 1305340-00-4
• 化学式: C₂₂H₄₀O₅
• 分子量: 384.557
• InChiKey: NVEMGDVIUWGMCQ-XJESJRCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  27.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,6S,9S)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-7-en-2-ol 在 四丙基高钌酸铵 、 sodium hexamethyldisilazane 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 (1R,6S,9S)-2-(bromomethylene)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-7-ene
  参考文献：
  名称：

  New C15-Substituted Active Vitamin D₃

  摘要：

  C15-Substituted 1 alpha,25-dihydroxyvitamin D-3 analogs were synthesized for the first time to investigate the effects of the modified CD-ring on biological activity concerning the agonistic positioning of helix-3 and helix-12 of the vitamin D receptor (VDR). X-ray cocrystallographic analysis proved that 0.6 angstrom shifts of the CD-ring and shrinking of the side chain were necessary to maintain the position of the 25-hydroxy group for proper interaction with helix-12. The 15-hydroxy-16-ene derivative showed higher binding affinity for hVDR than the natural hormone.

  DOI：

  10.1021/ol200828s
• 作为产物：
  描述：

  (1S,2S,6S,8R,9R)-2-[(tert-butyldimethylsilyl)oxy]-8,9-epoxy-6-methylbicyclo[4.3.0]nonan-7-one 在 正丁基锂 、 四丁基氟化铵 、 magnesium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 70.0h， 生成 (1R,2S,6S,9S)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-7-en-2-ol
  参考文献：
  名称：

  New C15-Substituted Active Vitamin D₃

  摘要：

  C15-Substituted 1 alpha,25-dihydroxyvitamin D-3 analogs were synthesized for the first time to investigate the effects of the modified CD-ring on biological activity concerning the agonistic positioning of helix-3 and helix-12 of the vitamin D receptor (VDR). X-ray cocrystallographic analysis proved that 0.6 angstrom shifts of the CD-ring and shrinking of the side chain were necessary to maintain the position of the 25-hydroxy group for proper interaction with helix-12. The 15-hydroxy-16-ene derivative showed higher binding affinity for hVDR than the natural hormone.

  DOI：

  10.1021/ol200828s