(R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)-phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-2-(3-methyl-3-buten-1-yl)-2-cyclohexen-1-one | 1115267-05-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)-phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-2-(3-methyl-3-buten-1-yl)-2-cyclohexen-1-one
• 英文别名: (5R)-5-[(Z)-1-[4-[tert-butyl(diphenyl)silyl]oxy-2-phenylmethoxyphenyl]-3-(2-methoxyethoxymethoxy)prop-1-en-2-yl]-2-(3-methylbut-3-enyl)cyclohex-2-en-1-one
• CAS: 1115267-05-4
• 化学式: C₄₇H₅₆O₆Si
• 分子量: 745.044
• InChiKey: IGXCEBMRPSYZPY-XHRLJDMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.49
• 重原子数：
  54
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)-phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-2-(3-methyl-3-buten-1-yl)-2-cyclohexen-1-one 在 叔丁基过氧化氢 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 22.0h， 生成
  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：

  (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 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以69%的产率得到(R,Z)-5-{3-[2-benzyloxy-4-(tert-butyldiphenylsilanyloxy)-phenyl]-1-[(2-methoxyethoxy)methoxy]-2-propen-2-yl}-2-(3-methyl-3-buten-1-yl)-2-cyclohexen-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

文献信息

• Synthetic studies toward miroestrols: trials for elongation of the methyl group of 5-substituted 2-methyl-2-cyclohexanone to 3-methyl-2-butenyl function
  作者：Fumihiro Ito、Takuya Kumamoto、Kentaro Yamaguchi、Tsutomu Ishikawa

  DOI：10.1016/j.tet.2008.11.055

  日期：2009.1

  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.