(S)-Spiro[4.5]dec-1-en-6-one | 220085-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-Spiro[4.5]dec-1-en-6-one
• 英文别名: (5S)-spiro[4.5]dec-3-en-10-one
• CAS: 220085-05-2
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: DQEWRUCBOXVWKE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-Spiro[4.5]dec-1-en-6-one 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 (S)-Spiro[4.5]deca-1,6-diene
  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：

  Trifluoro-methanesulfonic acid (5R,6R)-6-triethylsilanyloxy-spiro[4.5]dec-1-en-1-yl ester 在 palladium diacetate 、 甲酸 、 三乙胺 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (S)-Spiro[4.5]dec-1-en-6-one
  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