tert-butyl-[2-[[(Z)-[(2S,4S)-2-methoxy-4-methylcyclohexylidene]-trimethylsilyloxymethoxy]methyl]-3-methylcyclopent-2-en-1-yl]oxy-dimethylsilane | 1026335-14-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl-[2-[[(Z)-[(2S,4S)-2-methoxy-4-methylcyclohexylidene]-trimethylsilyloxymethoxy]methyl]-3-methylcyclopent-2-en-1-yl]oxy-dimethylsilane
• CAS: 1026335-14-7
• 化学式: C₂₅H₄₈O₄Si₂
• 分子量: 468.825
• InChiKey: MJNAMFRFIUMDIH-MWGNVMOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 tert-butyl-[2-[[(Z)-[(2S,4S)-2-methoxy-4-methylcyclohexylidene]-trimethylsilyloxymethoxy]methyl]-3-methylcyclopent-2-en-1-yl]oxy-dimethylsilane 在 盐酸 作用下， 生成 (S)-4-Methyl-cyclohex-1-enecarboxylic acid 5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclopent-1-enylmethyl ester 、 methyl (1R,2S,4S)-1-<(1S,3R)-3-(tert-butyldimethylsilyl)oxy-1-methyl-2-methylenecyclopentyl>-2-methoxy-4-methylcyclohexanecarboxylate 、 methyl (1R,2S,4S)-1-<(1R,3S)-3-(tert-butyldimethylsilyl)oxy-1-methyl-2-methylenecyclopentyl>-2-methoxy-4-methylcyclohexanecarboxylate
  参考文献：
  名称：

  Enantioselective synthesis of an ent-trichothecene

  摘要：

  A convergent route for the enantioselective synthesis of trichothecenes is described. A key step in the synthetic sequence is an Ireland-Claisen rearrangement that occurs with total facial selectivity and high diastereoselectivity. The relative stereochemistry about the vicinal quaternary centers of the major diastereomer is that of the trichothecene skeleton, but the absolute stereochemistry is opposite to that of the natural products.

  DOI：

  10.1016/s0040-4020(01)80841-3
• 作为产物：
  描述：

  <2-methyl-5-<(tert-butyldimethylsilyl)oxy>-1-cyclopentenyl>methanol 在 4-二甲氨基吡啶 、 TEA 、 甲基磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 tert-butyl-[2-[[(Z)-[(2S,4S)-2-methoxy-4-methylcyclohexylidene]-trimethylsilyloxymethoxy]methyl]-3-methylcyclopent-2-en-1-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Enantioselective synthesis of an ent-trichothecene

  摘要：

  A convergent route for the enantioselective synthesis of trichothecenes is described. A key step in the synthetic sequence is an Ireland-Claisen rearrangement that occurs with total facial selectivity and high diastereoselectivity. The relative stereochemistry about the vicinal quaternary centers of the major diastereomer is that of the trichothecene skeleton, but the absolute stereochemistry is opposite to that of the natural products.

  DOI：

  10.1016/s0040-4020(01)80841-3