Trifluoro-methanesulfonic acid (5R,6R)-6-triethylsilanyloxy-spiro[4.5]dec-1-en-1-yl ester | 220085-01-8

• 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: Trifluoro-methanesulfonic acid (5R,6R)-6-triethylsilanyloxy-spiro[4.5]dec-1-en-1-yl ester
• CAS: 220085-01-8
• 化学式: C₁₇H₂₉F₃O₄SSi
• 分子量: 414.562
• InChiKey: LFXCAQUFAHQOTI-CVEARBPZSA-N

物化性质

• 沸点：
  410.174±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.192±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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 (5R,6R)-6-triethylsilanyloxy-spiro[4.5]dec-1-en-1-yl ester 在 palladium diacetate 、 甲酸 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1, 4-addition to form carba-spirocyclic compounds

  摘要：

  Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered alpha,beta-unsaturated cyclic ketones having a 4-oxopentyl group at the beta-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8-dione, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01009-6
• 作为产物：
  描述：

  (5SR,6SR)-6-hydroxyspiro[4.5]decan-1-one 在 咪唑 、 4-二甲氨基吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 Trifluoro-methanesulfonic acid (5R,6R)-6-triethylsilanyloxy-spiro[4.5]dec-1-en-1-yl ester
  参考文献：
  名称：

  Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1, 4-addition to form carba-spirocyclic compounds

  摘要：

  Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered alpha,beta-unsaturated cyclic ketones having a 4-oxopentyl group at the beta-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8-dione, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01009-6