9,9-diphenyl-1,7-dioxaspiro[5.5]undec-4-ene | 1093662-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 9,9-diphenyl-1,7-dioxaspiro[5.5]undec-4-ene
• CAS: 1093662-77-1
• 化学式: C₂₁H₂₂O₂
• 分子量: 306.404
• InChiKey: WZIHYCXAOJOANP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,2,3,3,15,15,16,16-octamethyl-12,12-diphenyl-4,14-dioxa-3,15-disilaheptadec-8-yn-7-ol 在 对甲苯磺酸 、 gold(I) chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 9,9-diphenyl-1,7-dioxaspiro[5.5]undec-4-ene
  参考文献：
  名称：

  Controlling Regiochemistry in the Gold-Catalyzed Synthesis of Unsaturated Spiroketals

  摘要：

  A novel gold-catalyzed synthesis of unsaturated spiroketals that addresses regioselectivity issues commonly reported in metal-catalyzed spiroketalization of alkynes is reported. The reaction sequence is regulated by an acetonide protecting group which undergoes extrusion of acetone to deliver the desired spiroketals in good yields and diastereoselectivities. The reaction, which is carried out under very mild conditions employing AuCl as the catalyst, should be widely applicable in the synthesis of a broad range of spiroketals.

  DOI：

  10.1021/ol5024954

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.
• Controlling Regiochemistry in the Gold-Catalyzed Synthesis of Unsaturated Spiroketals
  作者：Paulo H. S. Paioti、John M. Ketcham、Aaron Aponick

  DOI：10.1021/ol5024954

  日期：2014.10.17

  A novel gold-catalyzed synthesis of unsaturated spiroketals that addresses regioselectivity issues commonly reported in metal-catalyzed spiroketalization of alkynes is reported. The reaction sequence is regulated by an acetonide protecting group which undergoes extrusion of acetone to deliver the desired spiroketals in good yields and diastereoselectivities. The reaction, which is carried out under very mild conditions employing AuCl as the catalyst, should be widely applicable in the synthesis of a broad range of spiroketals.