8-甲基-1,7-二氧杂螺<5.5>十一烷-2-基甲醇 | 84589-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 8-甲基-1,7-二氧杂螺<5.5>十一烷-2-基甲醇
• 英文名称: (8-methyl-1,7-dioxaspiro<5.5>undecan-2-yl)methanol
• CAS: 84589-07-1；104596-86-3；104596-89-6；105454-05-5；141115-30-2；141115-31-3；141115-32-4；141115-33-5；141115-60-8；141115-61-9；141115-62-0
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: XJYMRZITOLWEFW-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-甲基-1,7-二氧杂螺<5.5>十一烷-2-基甲醇 在 镍 sodium tetrahydroborate 、 三氟化硼乙醚 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 18.0h， 生成 (2S,10S)-undecane-2,10-diol
  参考文献：
  名称：

  Furanyl spiroketals as stereochemical relays in the synthesis of 1,9-anti diols: synthesis of insect pheromones

  摘要：

  A suite of spiroketal insect pheromones (15 and 17a-d) has been synthesised in good yield and with very high levels of diastereoselectivity via furanyl spiroketals. Remote asymmetric induction is achieved under thermodynamic control. The use of furanyl spiroketals as temporary scaffolds in the synthesis of 1,9-anti diols has been demonstrated with the synthesis of the swede midge pheromone (2S, 10S)-2, 10-diacetoxyundecane 1. The enzymatic resolution of a C-2 symmetric 1,9-anti diol was used as a confirmation of diastereomeric purity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.004
• 作为产物：
  描述：

  丁位己内酯 在 ruthenium trichloride sodium tetrahydroborate 、 sodium periodate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 生成 8-甲基-1,7-二氧杂螺<5.5>十一烷-2-基甲醇
  参考文献：
  名称：

  Furanyl spiroketals as stereochemical relays in the synthesis of 1,9-anti diols: synthesis of insect pheromones

  摘要：

  A suite of spiroketal insect pheromones (15 and 17a-d) has been synthesised in good yield and with very high levels of diastereoselectivity via furanyl spiroketals. Remote asymmetric induction is achieved under thermodynamic control. The use of furanyl spiroketals as temporary scaffolds in the synthesis of 1,9-anti diols has been demonstrated with the synthesis of the swede midge pheromone (2S, 10S)-2, 10-diacetoxyundecane 1. The enzymatic resolution of a C-2 symmetric 1,9-anti diol was used as a confirmation of diastereomeric purity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.004

文献信息

• Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis
  作者：Michael V. Perkins、Mark F. Jacobs、William Kitching、Peter J. Cassidy、Judith A. Lewis、Richard A. I. Drew

  DOI：10.1021/jo00038a027

  日期：1992.6

  Routes to the four regioisomeric 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols have been developed, and in the racemic series, mercury(II)-mediated reactions of appropriate dienone, hydroxy enone, dienedione, and hydroxy dienone systems have been exploited. Most of the epimeric pairs of alcohols (i.e. axial or equatorial) in the E,E, E,Z, or Z,E spiroacetal ring systems have been characterized by detailed H-1, C-13, and correlated NMR spectroscopy and mass spectrometry. Key enantiomers of these alcohols have been obtained by elaborating chiral starting materials such as D-mannitol, L-arabinose, poly(hydroxybutyrate), and in the case of the 5-hydroxy derivative, mandelonitrile lyase mediated formation of a key chiral cyanohydrin was employed. Most of the alcohols, as their trifluoroacetates, are resolved (into enantiomers) on a Lipodex A GC column, thus facilitating their identification from natural sources. In this way, the absolute configurations of a number of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols present in the rectal gland secretion of Bactrocera cucumis (cucumber fly) have been determined.
• Furanyl spiroketals as stereochemical relays in the synthesis of 1,9-anti diols: synthesis of insect pheromones
  作者：Shane Cahill、Lyndsay A. Evans、Matthew O’Brien

  DOI：10.1016/j.tetlet.2007.06.004

  日期：2007.8

  A suite of spiroketal insect pheromones (15 and 17a-d) has been synthesised in good yield and with very high levels of diastereoselectivity via furanyl spiroketals. Remote asymmetric induction is achieved under thermodynamic control. The use of furanyl spiroketals as temporary scaffolds in the synthesis of 1,9-anti diols has been demonstrated with the synthesis of the swede midge pheromone (2S, 10S)-2, 10-diacetoxyundecane 1. The enzymatic resolution of a C-2 symmetric 1,9-anti diol was used as a confirmation of diastereomeric purity. (c) 2007 Elsevier Ltd. All rights reserved.