4-{8-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.5]dec-8-yl}-2,4-dimethyl-cyclohex-2-enone | 194364-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-{8-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.5]dec-8-yl}-2,4-dimethyl-cyclohex-2-enone
• 英文别名: 4-[8-[2-[Tert-butyl(diphenyl)silyl]oxyethyl]-1,4-dioxaspiro[4.5]decan-8-yl]-2,4-dimethylcyclohex-2-en-1-one
• CAS: 194364-98-2
• 化学式: C₃₄H₄₆O₄Si
• 分子量: 546.822
• InChiKey: YEAJEWADEQOBKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{8-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.5]dec-8-yl}-2,4-dimethyl-cyclohex-2-enone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以98%的产率得到(1R,4R)-4-{8-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.5]dec-8-yl}-2,4-dimethyl-cyclohex-2-enol
  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：

  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