(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 | 1115266-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (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
• 英文别名: tert-butyl-[4-[(Z)-3-(2-methoxyethoxymethoxy)-2-[(1R,3R,6R)-6-methyl-5-(2-methylprop-2-enyl)-5-trimethylsilyloxy-7-oxabicyclo[4.1.0]heptan-3-yl]prop-1-enyl]-3-phenylmethoxyphenoxy]-diphenylsilane
• CAS: 1115266-97-1
• 化学式: C₅₀H₆₆O₇Si₂
• 分子量: 835.241
• InChiKey: OAPJWTBMOIDGPY-KSELEGFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.35
• 重原子数：
  59
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  三甲基氯硅烷 、 (1RS,2R,3R,5R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl]-1-[(2-methoxyethoxy)-methoxy]-2-propen-2-yl}-2,3-epoxy-2-methyl-1-(2-methyl-2-propen-1-yl)cyclohexanol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到(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
  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