(2S,6R,Z)-t-4-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-1-methylcyclohexan-r-1,c-2,c-6-triol | 1115267-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,6R,Z)-t-4-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-1-methylcyclohexan-r-1,c-2,c-6-triol
• CAS: 1115267-12-3
• 化学式: C₄₃H₅₄O₈Si
• 分子量: 726.982
• InChiKey: UBFSXICXAVGRHT-BMYFAXCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  106.84
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (1S,2R,3R,4R,6S,Z)-4-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-2,3-epoxy-1-methylcyclohexan-1,6-diol 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以32 mg的产率得到(2S,6R,Z)-t-4-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-1-methylcyclohexan-r-1,c-2,c-6-triol
  参考文献：
  名称：

  Synthetic studies toward miroestrols: trials for elongation of the methyl group of 5-substituted 2-methyl-2-cyclohexanone to 3-methyl-2-butenyl function

  摘要：

  Toward total synthesis of miroestrols (miroestrol and deoxymiroestrol), 3-methyl-2-butenyl function (endo-C5 unit) on D ring as a carbon chain for C and E rings was prepared by elongation of the methyl group in alpha-methyl-alpha.,beta-unsaturated ketone unit, and 3,5-dinitrobenzoyl group was introduced as a potential leaving group for the construction of B ring. The former was accomplished through a sequence of epoxide ring-opening, microwave-irradiated siloxy-Cope rearrangement, and isomerization of 3-methyl-3-butenyl function (exo-C5 unit) to endo-C5 unit. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.055