(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-trifluoromethanesulfonyloxy-cyclohex-2-enyl ester | 849676-23-9

• 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: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-trifluoromethanesulfonyloxy-cyclohex-2-enyl ester
• 英文别名: [(1S,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3-(trifluoromethylsulfonyloxy)cyclohex-2-en-1-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 849676-23-9
• 化学式: C₂₃H₃₅F₃O₈SSi
• 分子量: 556.673
• InChiKey: KTVJAVZYJQZKRZ-WWLNLUSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-trifluoromethanesulfonyloxy-cyclohex-2-enyl ester 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
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 4-(叔丁基二甲基硅氧)环己酮 、 (1S)-(-)-莰烷酰氯 以1.04 g的产率得到(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-3-trifluoromethanesulfonyloxy-cyclohex-2-enyl ester
  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.