(2S,4R,5R)-2-((tert-butyldiphenylsilyloxy)methyl)-1,6-dioxaspiro[4.6]undecan-4-ol | 1093663-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (2S,4R,5R)-2-((tert-butyldiphenylsilyloxy)methyl)-1,6-dioxaspiro[4.6]undecan-4-ol
• 英文别名: (2S,4R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,11-dioxaspiro[4.6]undecan-4-ol
• CAS: 1093663-06-9
• 化学式: C₂₆H₃₆O₄Si
• 分子量: 440.655
• InChiKey: BOZJPAUHOQQYGS-BBVWWWHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (7R,9S)-10-(tert-butyldiphenylsilyloxy)dec-5-yne-1,7,9-triol 在 氯[2-(二叔丁基磷)二苯基]金 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以31%的产率得到(1,7-dioxaspiro[5.5]undec-4-en-2-ylmethoxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals

  摘要：

  The gold-catalyzed cyclization of monopropargylic triols to form olefin-containing spiroketals is reported. The reactions are rapid and high yielding when 2 mol % of the catalyst generated in situ from Au[P(t-BU)(2)(o-biphenyI)]Cl and AgOTf is employed in THF at 0 degrees C. A range of differentially substituted triols leading to substituted 5- and 6-membered ring spiroketals were prepared and function well in the reaction.

  DOI：

  10.1021/ol802491m

文献信息

• Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals
  作者：Aaron Aponick、Chuan-Ying Li、Jean A. Palmes

  DOI：10.1021/ol802491m

  日期：2009.1.1

  The gold-catalyzed cyclization of monopropargylic triols to form olefin-containing spiroketals is reported. The reactions are rapid and high yielding when 2 mol % of the catalyst generated in situ from Au[P(t-BU)(2)(o-biphenyI)]Cl and AgOTf is employed in THF at 0 degrees C. A range of differentially substituted triols leading to substituted 5- and 6-membered ring spiroketals were prepared and function well in the reaction.