2,2,7-trimethyl-3,6-dithiatrideca-7,8-diene | 192370-91-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,2,7-trimethyl-3,6-dithiatrideca-7,8-diene
• CAS: 192370-91-5
• 化学式: C₁₄H₂₆S₂
• 分子量: 258.492
• InChiKey: JUIVNFPVXOUQJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  苯基溴化镁 、 2,2,7-trimethyl-3,6-dithiatrideca-7,8-diene 在 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 potassium iodide 作用下， 以67%的产率得到1,3-diphenylbuta-1,2-diene
  参考文献：
  名称：

  Novel Coupling Reactions of Dithioacetals with Organocuprate Reagents. Propargylic Dithioacetal as an Allene−1,3-Zwitterion Synthon

  摘要：

  DOI：

  10.1021/jo970700v
• 作为产物：
  描述：

  lithium di-tertbutyl cuprate 、 2-(hex-1-yn-1-yl)-2-methyldithiolane 在 甲醇 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到2,2,7-trimethyl-3,6-dithiatrideca-7,8-diene
  参考文献：
  名称：

  Novel Coupling Reactions of Dithioacetals with Organocuprate Reagents. Propargylic Dithioacetal as an Allene−1,3-Zwitterion Synthon

  摘要：

  DOI：

  10.1021/jo970700v

文献信息

• Novel Coupling Reactions of Dithioacetals with Organocuprate Reagents. Propargylic Dithioacetal as an Allene−1,3-Zwitterion Synthon
  作者：Hsian-Rong Tseng、Tien-Yau Luh

  DOI：10.1021/jo970700v

  日期：1997.7.1
• Umpolung of Carbon−Sulfur Bonds. Novel Synthesis of Substituted Allenes from Propargylic Dithioacetals
  作者：Hsian-Rong Tseng、Chin-Fa Lee、Lian-Ming Yang、Tien-Yau Luh

  DOI：10.1021/jo991032b

  日期：1999.11.1

  Umpolung of the carbon-sulfur bonds can be achieved by treatment of propargylic dithioacetals 1 with organocuprates. The organocopper intermediates 3 gave the corresponding allenyl thioethers 4 upon protonolysis. When alkyl halides were used, propargylic thioethers 5 were obtained exclusively. Transmetalation of organocopper intermediates 3 with ZnBr2 followed by Pd(PPh3)(4)- catalyzed coupling with vinylic or aryl halides afforded the corresponding allenyl thioethers 4. Either 4 or 5 reacted with Grignard reagents in the presence of NiCl2(dppf) to yield the corresponding allenes 9 or 10, respectively. The overall reaction can be considered to use 1 as allene-1,3-zwitterion synthons. The relative reactivities of a propargylic ether versus a propargylic dithioacetal toward an organocopper reagent were compared. The sulfur moiety apparently has higher reactivity toward the copper reagent.