(1R,3R,5R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)-phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-2-methylene-1-(2-methyl-2-propen-1-yl)-1,3-cyclohexadiol | 1115267-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,3R,5R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)-phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-2-methylene-1-(2-methyl-2-propen-1-yl)-1,3-cyclohexadiol
• CAS: 1115267-04-3
• 化学式: C₄₇H₅₈O₇Si
• 分子量: 763.059
• InChiKey: LACREBIHOPPZKO-PQGMFPROSA-N

反应信息

• 作为产物：
  描述：

  (1R,2RS,4R,6R,Z)-4-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-1,6-epoxy-1-methyl-2-(2-methyl-2-propen-1-yl)-2-trimethylsilanyloxylcyclohexane 在 正丁基锂 、 N-环己基异丙基胺 、 二甲基氯化铝 、 氯化铵 作用下， 以 正己烷 、 苯 、 水 为溶剂， 以50%的产率得到(1R,3RS,5R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)-phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-3-(2-methyl-2-propen-1-yl)-2-methylene-3-trimethylsilanyloxy-1-cyclohexanol
  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