(1'S,6'R)-4'-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,5-diethyl-3'-[(E)-pent-1-enyl]spiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-one | 901769-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'S,6'R)-4'-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,5-diethyl-3'-[(E)-pent-1-enyl]spiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-one
• CAS: 901769-79-7
• 化学式: C₃₅H₄₆O₅Si
• 分子量: 574.833
• InChiKey: HRHNRKAUKWUQIL-LACLKWJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'S,6'R)-4'-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,5-diethyl-3'-[(E)-pent-1-enyl]spiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-one 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以80%的产率得到(1R,6S)-3-Hydroxymethyl-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-2,5-dione
  参考文献：
  名称：

  Total Synthesis of the Interleukin-1β Converting Enzyme Inhibitor EI-1941-2 Using Tandem Oxa-electrocyclization/Oxidation¹

  摘要：

  The total synthesis of the interleukin-1 beta, converting enzyme inhibitor EI-1941-2 was achieved utilizing tandem oxidation/oxa-electrocyclization/oxidation to access a key alpha-pyrone intermediate. Support for the tandem reaction mechanism was obtained by evaluation of a stepwise oxidation protocol.

  DOI：

  10.1021/ol060954f
• 作为产物：
  描述：

  10-Bromo-11-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,3-diethyl-1,5-dioxaspiro[5.5]undeca-7,10-dien-9-one 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 三苯甲基氢过氧化物 、 sodium hexamethyldisilazane 、 D-(-)-酒石酸二异丙酯 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 (1'S,6'R)-4'-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,5-diethyl-3'-[(E)-pent-1-enyl]spiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-one
  参考文献：
  名称：

  Total Synthesis of the Interleukin-1β Converting Enzyme Inhibitor EI-1941-2 Using Tandem Oxa-electrocyclization/Oxidation¹

  摘要：

  The total synthesis of the interleukin-1 beta, converting enzyme inhibitor EI-1941-2 was achieved utilizing tandem oxidation/oxa-electrocyclization/oxidation to access a key alpha-pyrone intermediate. Support for the tandem reaction mechanism was obtained by evaluation of a stepwise oxidation protocol.

  DOI：

  10.1021/ol060954f

文献信息

• Total Synthesis of the Interleukin-1β Converting Enzyme Inhibitor EI-1941-2 Using Tandem Oxa-electrocyclization/Oxidation¹
  作者：Andrew S. Kleinke、Chaomin Li、Nicolas Rabasso、John A. Porco

  DOI：10.1021/ol060954f

  日期：2006.6.1

  The total synthesis of the interleukin-1 beta, converting enzyme inhibitor EI-1941-2 was achieved utilizing tandem oxidation/oxa-electrocyclization/oxidation to access a key alpha-pyrone intermediate. Support for the tandem reaction mechanism was obtained by evaluation of a stepwise oxidation protocol.