(5S*,6R*)-6-hydroxy-1-oxaspiro<4.5>decane-6-propanol | 141411-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (5S*,6R*)-6-hydroxy-1-oxaspiro<4.5>decane-6-propanol
• 英文别名: (5S*,6R*)-6-hydroxy-1-oxaspiro[4.5]decane-6-propanol；(5S,6R)-6-(3-hydroxypropyl)-1-oxaspiro[4.5]decan-6-ol
• CAS: 141411-95-2
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: KJZXYFQTBPRLDM-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S*,6R*)-6-hydroxy-1-oxaspiro<4.5>decane-6-propanol 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以84%的产率得到(5R*,6S*)-1,7-dioxadispiro<4.0.4.4>tetradecane
  参考文献：
  名称：

  Synthesis and molecular structure of belted spirocyclic tetrahydrofurans, a new class of preorganized hosts for cations

  摘要：

  The preparation and binding properties of spirocyclic tetrahydrofurans 7-11 are described. The condensation of cyclopentanone with 5-lithio-2,3-dihydrofuran (12) provided an alcohol which readily rearranged to ketone 14 under acidic conditions. ''Capping'' of the carbonyl group in 14 so as to generate a second spiro tetrahydrofuran subunit gave rise to 7 and 8. Starting with cyclobutanone, 2-fold ring expansion involving 12 provided the key reactions leading to 22 and 23, which were 'capped' as before. Crystal structure data are available for 9, 11, and 22. In addition, the variable-temperature NMR behavior of 7 and 10 was quantified by means of 2-D measurements. A detailed analysis is presented that shows the gauche effect to be of major importance in dictating the major conformation adopted by these ionophores. The binding properties of 7-11 have been assayed. Considerable variation was found, the efficiency being critically dependent upon the number of oxygen atoms, the relative stereochemistry of the C-O bonds, and the relative ease of conformational readjustment necessary to achieve proper organization around the oxophilic metal ion.

  DOI：

  10.1021/jo00040a041
• 作为产物：
  描述：

  6-allyl-1-oxaspiro<4.5>decan-6-ol 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 作用下， 生成 (5S*,6R*)-6-hydroxy-1-oxaspiro<4.5>decane-6-propanol 、 (5S*,6S*)-6-hydroxy-1-oxaspiro<4.5>decane-6-propanol
  参考文献：
  名称：

  Synthesis and molecular structure of belted spirocyclic tetrahydrofurans, a new class of preorganized hosts for cations

  摘要：

  The preparation and binding properties of spirocyclic tetrahydrofurans 7-11 are described. The condensation of cyclopentanone with 5-lithio-2,3-dihydrofuran (12) provided an alcohol which readily rearranged to ketone 14 under acidic conditions. ''Capping'' of the carbonyl group in 14 so as to generate a second spiro tetrahydrofuran subunit gave rise to 7 and 8. Starting with cyclobutanone, 2-fold ring expansion involving 12 provided the key reactions leading to 22 and 23, which were 'capped' as before. Crystal structure data are available for 9, 11, and 22. In addition, the variable-temperature NMR behavior of 7 and 10 was quantified by means of 2-D measurements. A detailed analysis is presented that shows the gauche effect to be of major importance in dictating the major conformation adopted by these ionophores. The binding properties of 7-11 have been assayed. Considerable variation was found, the efficiency being critically dependent upon the number of oxygen atoms, the relative stereochemistry of the C-O bonds, and the relative ease of conformational readjustment necessary to achieve proper organization around the oxophilic metal ion.

  DOI：

  10.1021/jo00040a041

文献信息

• π-Facial Diastereoselection in the 1,2-Addition of Allylmetal Reagents to 2-Methoxycyclohexanone and Tetrahydrofuranspiro-(2-cyclohexanone)
  作者：Leo A. Paquette、Paul C. Lobben

  DOI：10.1021/ja9536835

  日期：1996.1.1

  stereochemical course of the 1,2-addition of several allylmetal reagents and of the Normant Grignard [ClMgO(CH2)3MgCl] to 2-methoxycyclohexanone and tetrahydrofuranspiro-(2-cyclohexanone) has been determined. In four of the six substrates examined, a 4-tert-butyl group is present to serve as a conformational anchor. The neighboring methoxyl substituent is shown to be capable of engaging effectively in

  已经确定了几种烯丙基金属试剂和 Normant Grignard [ClMgO(CH2)3MgCl] 的 1,2-加成到 2-甲氧基环己酮和四氢呋喃螺-(2-环己酮) 的立体化学过程。在检测的六种底物中的四种中，存在一个 4-叔丁基作为构象锚。相邻的甲氧基取代基显示出能够有效参与螯合，尽管特殊情况可能另有规定。涉及烯丙基试剂作为水溶液中的亲核试剂的实验表明，水的存在不会抑制螯合控制的操作，这通常大大超过在无水介质中使用相应的镁、铈和铬试剂所能达到的效果。