[5-[Dimethyl(phenyl)silyl]-5-methylcyclohexen-1-yl] trifluoromethanesulfonate | 245657-53-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [5-[Dimethyl(phenyl)silyl]-5-methylcyclohexen-1-yl] trifluoromethanesulfonate
• CAS: 245657-53-8
• 化学式: C₁₆H₂₁F₃O₃SSi
• 分子量: 378.488
• InChiKey: SIDGSCRDSSBRHA-UHFFFAOYSA-N

物化性质

• 沸点：
  398.0±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [5-[Dimethyl(phenyl)silyl]-5-methylcyclohexen-1-yl] trifluoromethanesulfonate 在 四(三苯基膦)钯 sodium periodate 、 AD-mix-β 、 lithium chloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 14.5h， 生成 5-(Dimethyl-phenyl-silanyl)-5-methyl-cyclohex-1-enecarbaldehyde
  参考文献：
  名称：

  Total Synthesis of C-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar

  摘要：

  The total synthesis of urdamycinone B (1), a prototypical member of the C-glycosylangucycline antibiotics, was achieved by a novel and effective strategy without any protecting group in the sugar moiety. The unprotected C-glycosyljuglone 6 was effectively synthesized by the aryl C-glycosidation of 1,5-naphthalenediol (16) with the totally unprotected D-olivose (8) and the subsequent regioselective photooxygenation of the resultant C-glycosylnaphthalenediol 17. On the other hand, the diene 7 was prepared from 3-methyl-2-cyclohexen-1-one (9) in a short step via the cross-coupling of the vinyl triflate 20 and vinylbutyltin (21) and the Wittig reaction of the aldehyde 24 and the phosphine 25. Finally, the regioselective Diels-Alder reaction of the unprotected C-glycosyljuglone 6 and the diene 7, followed by the regioselecitive introduction of the ketone function at the C1 position, led to the total synthesis of 1.

  DOI：

  10.1021/jo990648y
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 3-(dimethyl(phenyl)silyl)-3-methylcyclohexanone 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到[5-[Dimethyl(phenyl)silyl]-5-methylcyclohexen-1-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels–Alder reaction of C-glycosyl juglone

  摘要：

  The total synthesis of C-glycosyl angucycline, urdamycinone B 1, was achieved via C-glycosidation of naphthol 6 and the unprotected o-olivose 7, and Diels-Alder reaction of the unprotected C-glycosyl juglone 9 and the diene 17 as the key steps.

  DOI：

  10.1039/cc9960000225

文献信息

• Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels–Alder reaction of C-glycosyl juglone
  作者：Goh Matsuo、Yuko Miki、Masaya Nakata、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1039/cc9960000225

  日期：——

  The total synthesis of C-glycosyl angucycline, urdamycinone B 1, was achieved via C-glycosidation of naphthol 6 and the unprotected o-olivose 7, and Diels-Alder reaction of the unprotected C-glycosyl juglone 9 and the diene 17 as the key steps.
• Total Synthesis of <i>C</i>-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar
  作者：Goh Matsuo、Yuko Miki、Masaya Nakata、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1021/jo990648y

  日期：1999.9.1

  The total synthesis of urdamycinone B (1), a prototypical member of the C-glycosylangucycline antibiotics, was achieved by a novel and effective strategy without any protecting group in the sugar moiety. The unprotected C-glycosyljuglone 6 was effectively synthesized by the aryl C-glycosidation of 1,5-naphthalenediol (16) with the totally unprotected D-olivose (8) and the subsequent regioselective photooxygenation of the resultant C-glycosylnaphthalenediol 17. On the other hand, the diene 7 was prepared from 3-methyl-2-cyclohexen-1-one (9) in a short step via the cross-coupling of the vinyl triflate 20 and vinylbutyltin (21) and the Wittig reaction of the aldehyde 24 and the phosphine 25. Finally, the regioselective Diels-Alder reaction of the unprotected C-glycosyljuglone 6 and the diene 7, followed by the regioselecitive introduction of the ketone function at the C1 position, led to the total synthesis of 1.