(1R,2S,4S,Z)-4-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-1-(3-methyl-3-buten-1-yl)-cyclohexan-1,2-diol | 1115267-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,2S,4S,Z)-4-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-1-(3-methyl-3-buten-1-yl)-cyclohexan-1,2-diol
• 英文别名: (1S,2S,4R)-4-[(Z)-1-[4-[tert-butyl(diphenyl)silyl]oxy-2-phenylmethoxyphenyl]-3-(2-methoxyethoxymethoxy)prop-1-en-2-yl]-1-(3-methylbut-3-enyl)cyclohexane-1,2-diol
• CAS: 1115267-20-3
• 化学式: C₄₇H₆₀O₇Si
• 分子量: 765.075
• InChiKey: KMWZLYHGEMBLNP-HBIAWAIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,Z)-4-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-1-(3-methyl-3-buten-1-yl)-cyclohexan-1,2-diol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%的产率得到(1S,2S,4R,Z)-4-[3-{2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl}-1-{(2-methoxyethoxy)methoxy}-2-propen-2-yl]-1,2-(dimethylmethylenedioxy)-1-(3-methyl-3-buten-1-yl)-cyclohexane
  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,3R,5S,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-2,3-epoxy-2-(3-methyl-3-buten-1-yl)cyclohexanol 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以89%的产率得到(1R,2S,4S,Z)-4-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-1-(3-methyl-3-buten-1-yl)-cyclohexan-1,2-diol
  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