spiro[5.5]undecane-2,8-dione | 70682-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiro[5.5]undecane-2,8-dione
• 英文别名: spiro[5.5]undecane-4,10-dione
• CAS: 70682-04-1
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: ILKUIQCOFNIYKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 以 乙醚 为溶剂， 反应 2.0h， 生成 spiro[5.5]undecane-2,8-dione
  参考文献：
  名称：

  Stereoselectivity in formation of spiro[5.5]undecanes by cationic .pi. cyclization

  摘要：

  DOI：

  10.1021/jo01330a003

文献信息

• Activation of carbonyl function by 1,2-diol; novel asymmetric spirocyclization based on acid-catalysed conjugate addition
  作者：Hiroshi Suemune、Youichi Takahashi、Kiyoshi Sakai

  DOI：10.1039/c39930001858

  日期：——

  Novel asymmetric spirocyclization of 3-(4-oxopentyl)cyclohex-2-en-1-one 3 based on activation of carbonyl function by BF3-(S,S)-cyclohexane-1,2-diol system has been studied to afford the C2-symmetric dione (–)-5 of 85% enantiomeric excess (e.e.) in 86% yield.

  基于 BF3-(S,S)-环己烷-1,2-二醇体系对羰基功能的活化，研究了 3-(4-氧代戊基)环己-2-烯-1-酮 3 的新型不对称螺环化，得到了对映体过量率为 85% (e.e.)的 C2 对称二酮 (-)-5，收率为 86%。
• Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1, 4-addition to form carba-spirocyclic compounds
  作者：Satoshi Yamada、Satoru Karasawa、Youichi Takahashi、Mariko Aso、Hiroshi Suemune

  DOI：10.1016/s0040-4020(98)01009-6

  日期：1998.12

  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.