tert-Butyl-{2-[8-(4-methoxy-1,3-dimethyl-cyclohexa-2,4-dienyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-ethoxy}-diphenyl-silane | 194364-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-{2-[8-(4-methoxy-1,3-dimethyl-cyclohexa-2,4-dienyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-ethoxy}-diphenyl-silane
• 英文别名: Tert-butyl-[2-[8-(4-methoxy-1,3-dimethylcyclohexa-2,4-dien-1-yl)-1,4-dioxaspiro[4.5]decan-8-yl]ethoxy]-diphenylsilane
• CAS: 194364-97-1
• 化学式: C₃₅H₄₈O₄Si
• 分子量: 560.849
• InChiKey: ZICQIMJVOQDPPC-UHFFFAOYSA-N

物化性质

• 沸点：
  604.6±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  tert-Butyl-{2-[8-(4-methoxy-1,3-dimethyl-cyclohexa-2,4-dienyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-ethoxy}-diphenyl-silane 在 草酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.3h， 以68%的产率得到4-{8-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.5]dec-8-yl}-2,4-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  A Synthesis of (±)-Stemodinone:  An Application of Organoiron Chemistry to the Construction of Sterically Congested Quaternary Carbon Centers

  摘要：

  A synthesis of racemic stemodinone is described, using tricarbonyl(1-5-eta-4-methoxy-1,3-dimethylcyclohexadienyl)iron( I) hexafluorophosphate (9) as an electrophile that is the A-ring precursor. Reaction of 9 with the tin enolate from 4,4-(ethylenedioxy)cyclohexanecarbaldehyde proceeded with excellent regioselectivity and high yield to generate an intermediate representing the A and C rings of the target molecule, The B ring was constructed by introducing a two-carbon electrophilic group onto the A ring, followed by ring closure using an intramolecular enolate alkylation. installation of the D ring and manipulation to give the final product followed transformations precedented with this series of compounds.

  DOI：

  10.1021/jo9705475
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 十二/十四烷基二甲基氧化胺 作用下， 以 苯 为溶剂， 反应 18.0h， 以91%的产率得到tert-Butyl-{2-[8-(4-methoxy-1,3-dimethyl-cyclohexa-2,4-dienyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-ethoxy}-diphenyl-silane
  参考文献：
  名称：

  A Synthesis of (±)-Stemodinone:  An Application of Organoiron Chemistry to the Construction of Sterically Congested Quaternary Carbon Centers

  摘要：

  A synthesis of racemic stemodinone is described, using tricarbonyl(1-5-eta-4-methoxy-1,3-dimethylcyclohexadienyl)iron( I) hexafluorophosphate (9) as an electrophile that is the A-ring precursor. Reaction of 9 with the tin enolate from 4,4-(ethylenedioxy)cyclohexanecarbaldehyde proceeded with excellent regioselectivity and high yield to generate an intermediate representing the A and C rings of the target molecule, The B ring was constructed by introducing a two-carbon electrophilic group onto the A ring, followed by ring closure using an intramolecular enolate alkylation. installation of the D ring and manipulation to give the final product followed transformations precedented with this series of compounds.

  DOI：

  10.1021/jo9705475