(2S,5R,Z)-5-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-2-hydroxy-2-(3-methyl-2-buten-1-yl)-cyclohexan-1-one | 1115267-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,5R,Z)-5-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-2-hydroxy-2-(3-methyl-2-buten-1-yl)-cyclohexan-1-one
• CAS: 1115267-24-7
• 化学式: C₄₇H₅₈O₇Si
• 分子量: 763.059
• InChiKey: SDJNWVNMPAPKRT-CZKBKFLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  55.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,5R,Z)-5-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-2-hydroxy-2-(3-methyl-2-buten-1-yl)-cyclohexan-1-one 在 4-甲基苯磺酸吡啶 作用下， 以 丁酮 为溶剂， 反应 0.1h， 以48%的产率得到(2S,5R,Z)-5-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-hydroxy-2-propen-2-yl]-2-hydroxy-2-(3-methyl-2-buten-1-yl) cyclohexan-1-one
  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
• 作为产物：
  描述：

  (1S,2S,4R,Z)-4-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-1-(3-methyl-2-buten-1-yl)-cyclohexane-1,2-diol 在 2-碘酰苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 以90%的产率得到(2S,5R,Z)-5-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-2-hydroxy-2-(3-methyl-2-buten-1-yl)-cyclohexan-1-one
  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