Trifluoro-methanesulfonic acid (4aR,7R,8aR)-4a-methyl-7-(1-methyl-1-triethylsilanyloxy-ethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester | 253864-06-1

• 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: Trifluoro-methanesulfonic acid (4aR,7R,8aR)-4a-methyl-7-(1-methyl-1-triethylsilanyloxy-ethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester
• 英文别名: [(4aR,7R,8aR)-4a-methyl-7-(2-triethylsilyloxypropan-2-yl)-4,5,6,7,8,8a-hexahydro-3H-naphthalen-1-yl] trifluoromethanesulfonate
• CAS: 253864-06-1
• 化学式: C₂₁H₃₇F₃O₄SSi
• 分子量: 470.669
• InChiKey: QERAEAITHKXQMR-FUHIMQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (4aR,7R,8aR)-4a-methyl-7-(1-methyl-1-triethylsilanyloxy-ethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester 在 六甲基磷酰三胺 、 四(三苯基膦)钯 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 18.08h， 生成 (+)-δ-selinene
  参考文献：
  名称：

  A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

  摘要：

  The ether extract of the liverwort Porella perrottetiana afforded (-)-alpha-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-alpha-eudesmol strongly suggested that the positive values (e.g. + 28.5 degrees) described in many previous papers should be revised. Since the absolute configuration of (-)-alpha-eudesmol was identical to that of (+)-beta-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-alpha-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-alpha-eudesmol will be discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00299-x
• 作为产物：
  描述：

  beta-桉叶醇 在 咪唑 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 Trifluoro-methanesulfonic acid (4aR,7R,8aR)-4a-methyl-7-(1-methyl-1-triethylsilanyloxy-ethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

  摘要：

  The ether extract of the liverwort Porella perrottetiana afforded (-)-alpha-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-alpha-eudesmol strongly suggested that the positive values (e.g. + 28.5 degrees) described in many previous papers should be revised. Since the absolute configuration of (-)-alpha-eudesmol was identical to that of (+)-beta-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-alpha-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-alpha-eudesmol will be discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00299-x