16α-hydroxymethyl-3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17β-ol | 158498-06-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 16α-hydroxymethyl-3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17β-ol
• CAS: 158498-06-7
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: ISFAYOFEACGJRV-ZCHQJCHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  16α-hydroxymethyl-3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17β-ol 在 吡啶 、 六甲基磷酰三胺 、 氢氧化钾 、 copper(l) iodide 、 三甲基氯硅烷 、 甲基锂 、 四氯化钛 、 二异丁基氢化铝 、 臭氧 、 三苯基膦 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 43.66h， 生成 [(1S,2R,11S,14S,15R,16R)-15-acetyloxy-7-hydroxy-14-methyl-16-pentacyclo[13.2.2.01,14.02,11.05,10]nonadeca-5(10),6,8-trienyl] acetate
  参考文献：
  名称：

  Cycloaddition-fragmentation route to 14β-allylestrone and the derived 14α,17α-ethano analogue of estriol

  摘要：

  3-Methoxyestra-1,3,5(10),14,16-pentaen-17-yl acetate (1) undergoes efficient baron trifluoride catalysed cycloaddition at 20 degrees C with. acrolein to give the corresponding 17 beta-acetoxy 14 alpha,17 alpha-etheno 16 alpha-carbaldebyde (2). The derived 16 alpha-tosyloxymethyl intermediates are converted via Wharton fragmentation into 14 beta-allyl derivatives of estrone. Oxidative cleavage of 14-allyl-3-methoxy-14 beta-estra-1,3,5(10)-trien-17-one (14) furnishes the 14 beta-formylmethyl derivative (17). Intramolecular reductive cyclisation of 17, followed by stepwise protection-deprotection of functionality provides an efficient synthetic route to 14,17 alpha-ethanoestra-1,3,5(10)-triene-3,16 alpha,17 beta-triol (23), the structure of which is confirmed with the aid of X-ray crystallographic analysis of the derived triacetate.

  DOI：

  10.1016/s0040-4020(01)80653-0
• 作为产物：
  描述：

  17β-acetoxy-3-methoxy-14,17α-ethenooestra-1,3,5(10)-triene-16α-carbaldahyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以74%的产率得到16α-hydroxymethyl-3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17β-ol
  参考文献：
  名称：

  Cycloaddition-fragmentation route to 14β-allylestrone and the derived 14α,17α-ethano analogue of estriol

  摘要：

  3-Methoxyestra-1,3,5(10),14,16-pentaen-17-yl acetate (1) undergoes efficient baron trifluoride catalysed cycloaddition at 20 degrees C with. acrolein to give the corresponding 17 beta-acetoxy 14 alpha,17 alpha-etheno 16 alpha-carbaldebyde (2). The derived 16 alpha-tosyloxymethyl intermediates are converted via Wharton fragmentation into 14 beta-allyl derivatives of estrone. Oxidative cleavage of 14-allyl-3-methoxy-14 beta-estra-1,3,5(10)-trien-17-one (14) furnishes the 14 beta-formylmethyl derivative (17). Intramolecular reductive cyclisation of 17, followed by stepwise protection-deprotection of functionality provides an efficient synthetic route to 14,17 alpha-ethanoestra-1,3,5(10)-triene-3,16 alpha,17 beta-triol (23), the structure of which is confirmed with the aid of X-ray crystallographic analysis of the derived triacetate.

  DOI：

  10.1016/s0040-4020(01)80653-0