1-[(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enyl]-2,2,2-trifluoro-ethanone | 849676-27-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-[(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enyl]-2,2,2-trifluoro-ethanone
• 英文别名: 1-[(3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxycyclohexen-1-yl]-2,2,2-trifluoroethanone
• CAS: 849676-27-3
• 化学式: C₁₅H₂₅F₃O₃Si
• 分子量: 338.442
• InChiKey: FZEZKRLAHDZJFY-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异丙烯基溴化镁 、 1-[(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enyl]-2,2,2-trifluoro-ethanone 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-[(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enyl]-1,1,1-trifluoro-3-methyl-but-3-en-2-ol 、 1-[(1R,2S,3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isopropenyl-3-methoxy-cyclohexyl]-2,2,2-trifluoro-ethanone
  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：

  (3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enecarbaldehyde 在 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 1-[(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enyl]-2,2,2-trifluoro-ethanone
  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.