Spiro<5.5>undeca-1,7-dien | 39170-86-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: Spiro<5.5>undeca-1,7-dien
• 英文别名: spiro[5.5]undeca-4,10-diene
• CAS: 39170-86-0
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: SMFOMOFFYYAWJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  Spiro<5.5>undeca-1,7-dien 在 ruthenium(IV) oxide 、 sodium hydroxide 、 sodium periodate 、 硼烷四氢呋喃络合物 、 双氧水 作用下， 以 四氯化碳 、 水 为溶剂， 反应 51.0h， 生成 spiro[5.5]undecane-2,8-dione
  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：

  生成 Spiro<5.5>undeca-1,7-dien
  参考文献：
  名称：

  从空间位烯烃的合成硫代碳酸酯的热解阻醇ø -酯

  摘要：

  用O -4-甲基苯基氯硫代甲酸酯将位阻受阻的醇（如（I； R = H））酰化，并通过热解将所得的硫代碳酸酯转化为烯烃。

  DOI：

  10.1039/c39720001215

文献信息

• Spirocycle assembly through selective tandem ring closing metathesis reactions
  作者：Martin J. Bassindale、Peter Hamley、Andreas Leitner、Joseph P.A. Harrity

  DOI：10.1016/s0040-4039(99)00375-5

  日期：1999.4

  A range of functionalised spirocyclic systems have been prepared under mild and neutral conditions by tandem selective ring closing olefin metathesis reactions. Additionally, a marked preference for 5-membered ring closure over 7-membered ring closure was observed which appears to be a result of a kinetically favoured cyclisation process. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of olefins from sterically hindered alcohols by pyrolysis of thiocarbonate O-esters
  作者：H. Gerlach、Tran Thi Houng、W. Müller

  DOI：10.1039/c39720001215

  日期：——

  Sterically hindered alcohols e.g.(I; R = H) were acylated with O-4-methylphenyl chlorothioformate in high yield and the resulting thiocarbonates were converted into olefins by pyrolysis.

  用O -4-甲基苯基氯硫代甲酸酯将位阻受阻的醇（如（I； R = H））酰化，并通过热解将所得的硫代碳酸酯转化为烯烃。
• 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.