2-cyclohexyl-2-hex-1-ynyl-1,3-dithiolane | 950758-19-7

• 分子结构分类: 有机化合物
• 英文名称: 2-cyclohexyl-2-hex-1-ynyl-1,3-dithiolane
• CAS: 950758-19-7
• 化学式: C₁₅H₂₄S₂
• 分子量: 268.488
• InChiKey: VJLLHRGRAKJXNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl-2-hex-1-ynyl-1,3-dithiolane 在 甲基碘化镁 、 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 1.0h， 生成 3-cyclohexyl-2-methylnon-2-en-4-yne
  参考文献：
  名称：

  Iron-Promoted Elimination of β-Thioalkoxy Alcohols. Olefination by Coupling of a Carbonyl Group with a Dithioacetal

  摘要：

  Treatment of propargylic dithiolanes with (BuLi)-Bu-n followed by a carbonyl electrophile yields the corresponding propargylic dithioacetals. Upon treatment with 1 equiv of Fe(acac)(3) and excess MeMgI, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.

  DOI：

  10.1021/ol701579f
• 作为产物：
  描述：

  (2-cyclohexyl-1,3-dithiolan-2-ylethynyl)-trimethylsilane 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 0.5h， 生成 2-cyclohexyl-2-hex-1-ynyl-1,3-dithiolane
  参考文献：
  名称：

  Iron-Promoted Elimination of β-Thioalkoxy Alcohols. Olefination by Coupling of a Carbonyl Group with a Dithioacetal

  摘要：

  Treatment of propargylic dithiolanes with (BuLi)-Bu-n followed by a carbonyl electrophile yields the corresponding propargylic dithioacetals. Upon treatment with 1 equiv of Fe(acac)(3) and excess MeMgI, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.

  DOI：

  10.1021/ol701579f

文献信息

• Mercuric acetate-mediated annulation of homopropargylic alcohols having thioether substituent. A general route for the synthesis of tetrasubstituted furans from propargylic dithioacetals
  作者：Chih-Wei Chen、Tien-Yau Luh

  DOI：10.1016/j.tetlet.2009.02.043

  日期：2009.7

  Treatment of an alkyl-substituted propargylic dithioacetal with (BuLi)-Bu-n followed by an aldehyde furnishes thio-substituted homopropargylic alcohol 7 which undergoes annulation in the presence of two equivalents of mercury acetate to give the corresponding mercurio-substituted furan 12. Reaction of 12 with iodine gives iodofuran in moderate to good yield. (C) 2009 Elsevier Ltd. All rights reserved.