2-ethynyl-2-isopropyl-1,3-dithiolane | 950758-25-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2-ethynyl-2-isopropyl-1,3-dithiolane
• CAS: 950758-25-5
• 化学式: C₈H₁₂S₂
• 分子量: 172.315
• InChiKey: HVZJZBMZDAOYGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-ethynyl-2-isopropyl-1,3-dithiolane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 3-methyl-4-(1,4-dithiaoctyl)-4-isopropyl-1-trimethylsilyldeca-1,5-diyn-3-ol
  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：

  4-methyl-1-(trimethylsilyl)pent-1-yn-3-one 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-ethynyl-2-isopropyl-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

• Elimination of β-Thioalkoxy Alcohols under Mitsunobu Conditions. A New Synthesis of Conjugated Enynes from Propargylic Dithioacetals
  作者：Chih-Wei Chen、Tien-Yau Luh

  DOI：10.1021/jo8013885

  日期：2008.11.7

  Treatment of propargylic dithiolanes 1 with (n)BuLi followed by a carbonyl electrophile yields the corresponding homopropargylic alcohol 3. Upon treatment with 2 equiv of PPh3 and DIAD, elimination of SR and OH moieties from 3 affords the corresponding olefins 4 in moderate to good yield. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.

  用（n）BuLi然后用羰基亲电试剂处理炔丙基二硫杂环戊烷1得到相应的均炔丙基醇3。用2当量的PPh3和DIAD处理后，从3中除去SR和OH部分得到相应的烯烃4，产率中等至良好。该反应可以被认为是两种不同的羰基当量的麦克默里偶联的替代方法。