(Z)-4-(4-(triphenylsilyl)-2-oxodihydrofuran-3(2H)-ylidene)-2,2-dimethylbutanal | 1256752-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (Z)-4-(4-(triphenylsilyl)-2-oxodihydrofuran-3(2H)-ylidene)-2,2-dimethylbutanal
• 英文别名: (4Z)-2,2-dimethyl-4-(2-oxo-4-triphenylsilyloxolan-3-ylidene)butanal
• CAS: 1256752-72-3
• 化学式: C₂₈H₂₈O₃Si
• 分子量: 440.614
• InChiKey: XUTXVEXEZYKXSR-XIEYBQDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-(4-(triphenylsilyl)-2-oxodihydrofuran-3(2H)-ylidene)-2,2-dimethylbutanal 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以88%的产率得到rac-(3S,4R)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)-4-(triphenylsilyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  SmI₂-Mediated Radical Cyclizations Directed by a C−Si Bond

  摘要：

  The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI2 results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.

  DOI：

  10.1021/ol102278c
• 作为产物：
  描述：

  三苯基氯硅烷 在 水 、 sodium methylate 、 copper(l) cyanide 、 lithium 、 三乙胺 、 calcium carbonate 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 52.5h， 生成 (Z)-4-(4-(triphenylsilyl)-2-oxodihydrofuran-3(2H)-ylidene)-2,2-dimethylbutanal
  参考文献：
  名称：

  SmI₂-Mediated Radical Cyclizations Directed by a C−Si Bond

  摘要：

  The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI2 results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.

  DOI：

  10.1021/ol102278c

文献信息

• SmI₂-Mediated Radical Cyclizations Directed by a C−Si Bond
  作者：Hassan Y. Harb、Karl D. Collins、Jose V. Garcia Altur、Sue Bowker、Leonie Campbell、David J. Procter

  DOI：10.1021/ol102278c

  日期：2010.12.3

  The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI2 results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.