(4R,4aR,11bS)-methyl 8-acetoxy-1,2,3,4,4a,5,6,11b-octahydro-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylate | 1612793-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (4R,4aR,11bS)-methyl 8-acetoxy-1,2,3,4,4a,5,6,11b-octahydro-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylate
• CAS: 1612793-56-2
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: XQEIFBXIWQCYLQ-CEMLEFRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (1R,4aS,10aR)-7-(2-Chloro-acetyl)-6-hydroxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 26.0h， 生成 (4R,4aR,11bS)-methyl 8-acetoxy-1,2,3,4,4a,5,6,11b-octahydro-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylate
  参考文献：
  名称：

  A Fast Entry to Furanoditerpenoid-Based Hedgehog Signaling Inhibitors: Identifying Essential Structural Features

  摘要：

  New, small molecule Hedgehog (Hh) pathway inhibitors, such as the furanoditerpenoid taepeenin D, are of high medicinal importance. To establish key structure-activity relationships (SARs) for this lead, a synthetic sequence has been developed for the expedient preparation of several derivatives and their evaluation as Hh inhibitors exploiting its structural similarity to abietic acid. While C(14) substitution is not essential for biological activity, the presence of a hydrogen bond acceptor at C(6) and an intact benzofuran moiety are.

  DOI：

  10.1021/ol501370j