2-(trimethylsiloxy)furan | 65769-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-(trimethylsiloxy)furan
• 英文别名: Trimethyl[(oxolan-2-yl)oxy]silane；trimethyl(oxolan-2-yloxy)silane
• CAS: 65769-92-8
• 化学式: C₇H₁₆O₂Si
• 分子量: 160.288
• InChiKey: YEKUVQLVLUJGLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(trimethylsiloxy)furan 、 2,3-O-isopropylidene-4-O-benzyl-L-threose N-benzylimine 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以77%的产率得到5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone
  参考文献：
  名称：

  Total syntheses of (+)-2,8,8a-tri-epi-swainsonine and (-)-1-epi-swainsonine

  摘要：

  Parallel syntheses of the title swainsonine-related enantiomers 9 and 15 were achieved in five steps and in 55% overall yield via enantiomeric threose N-benzylimines 4 and 10, derived from L- and D-tartaric acid, respectively. A stereospecific 4+4 homologative procedure using 2-(trimethylsiloxy)furan (TMSOF), obtained from 2-furaldehyde, was employed to form the eight-carbon skeleton of the indolizidine triols and to install the proper chirality. Remarkably, the syntheses were completed by cyclizations of tetrahydroxypiperidine intermediates 8 and 14 to 9 and 15, respectively (ca. 90 %; PPh3, CCl4, Et3N in DMF at room temperature), without recourse to protecting groups.

  DOI：

  10.1021/jo00064a031
• 作为产物：
  描述：

  2-羟基四氢呋喃 、 六甲基二硅氮烷 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以82%的产率得到2-(trimethylsiloxy)furan
  参考文献：
  名称：

  Lakouraj; Akbari, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 5, p. 1165 - 1167

  摘要：

  DOI：

文献信息

• BRINKMAN, K. C.;GLADYSZ, J. A., ORGANOMETALLICS, 1984, 3, N 1, 147-155
  作者：BRINKMAN, K. C.、GLADYSZ, J. A.

  DOI：——

  日期：——
• Lakouraj; Akbari, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 5, p. 1165 - 1167
  作者：Lakouraj、Akbari

  DOI：——

  日期：——
• Total syntheses of (+)-2,8,8a-tri-epi-swainsonine and (-)-1-epi-swainsonine
  作者：Giovanni Casiraghi、Gloria Rassu、Pietro Spanu、Luigi Pinna、Fausta Ulgheri

  DOI：10.1021/jo00064a031

  日期：1993.6

  Parallel syntheses of the title swainsonine-related enantiomers 9 and 15 were achieved in five steps and in 55% overall yield via enantiomeric threose N-benzylimines 4 and 10, derived from L- and D-tartaric acid, respectively. A stereospecific 4+4 homologative procedure using 2-(trimethylsiloxy)furan (TMSOF), obtained from 2-furaldehyde, was employed to form the eight-carbon skeleton of the indolizidine triols and to install the proper chirality. Remarkably, the syntheses were completed by cyclizations of tetrahydroxypiperidine intermediates 8 and 14 to 9 and 15, respectively (ca. 90 %; PPh3, CCl4, Et3N in DMF at room temperature), without recourse to protecting groups.