[(3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexen-1-yl] trifluoromethanesulfonate | 849676-24-0

• 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: [(3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexen-1-yl] trifluoromethanesulfonate
• CAS: 849676-24-0
• 化学式: C₁₄H₂₅F₃O₅SSi
• 分子量: 390.496
• InChiKey: AYVWJEBZKXQXDU-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲醇 、 一氧化碳 、 [(3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexen-1-yl] trifluoromethanesulfonate 在 palladium diacetate 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以322 mg的产率得到methyl (3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexene-1-carboxylate
  参考文献：
  名称：

  Enantioselective Approaches to Potential MetAP-2 Reversible Inhibitors

  摘要：

  Enantioselective deprotonation of 4-substituted cyclohexanones and highly stereoselective conjugate addition of higher order mixed cuprates were the key steps in a concise synthesis of fumagalone-related molecules. The origin of the (low) biological activity of the new compounds as compared to fumagalone is briefly discussed.

  DOI：

  10.1021/jo047858h
• 作为产物：
  描述：

  4-(叔丁基二甲基硅氧)环己酮 在 二异丁基氢化铝 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 19.0h， 生成 [(3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexen-1-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Enantioselective Approaches to Potential MetAP-2 Reversible Inhibitors

  摘要：

  Enantioselective deprotonation of 4-substituted cyclohexanones and highly stereoselective conjugate addition of higher order mixed cuprates were the key steps in a concise synthesis of fumagalone-related molecules. The origin of the (low) biological activity of the new compounds as compared to fumagalone is briefly discussed.

  DOI：

  10.1021/jo047858h

文献信息

• Enantioselective Approaches to Potential MetAP-2 Reversible Inhibitors
  作者：Vincent Rodeschini、Pierre Van de Weghe、Emmanuel Salomon、Céline Tarnus、Jacques Eustache

  DOI：10.1021/jo047858h

  日期：2005.3.1

  Enantioselective deprotonation of 4-substituted cyclohexanones and highly stereoselective conjugate addition of higher order mixed cuprates were the key steps in a concise synthesis of fumagalone-related molecules. The origin of the (low) biological activity of the new compounds as compared to fumagalone is briefly discussed.