(4R,5S)-2,4,5,7-Tetramethyl-octa-2,6-diene-4,5-diol | 80885-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-2,4,5,7-Tetramethyl-octa-2,6-diene-4,5-diol
• 英文别名: (4S,5R)-2,4,5,7-tetramethylocta-2,6-diene-4,5-diol
• CAS: 80885-65-0
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: TUCWJXMQYQTUPB-TXEJJXNPSA-N

物化性质

• 沸点：
  70-80 °C(Press: 0.6 Torr)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 以40%的产率得到
  参考文献：
  名称：

  PONS, JEAN-MARC;SANTELLI, MAURICE, J. ORG. CHEM., 54,(1989) N, C. 877-884

  摘要：

  DOI：

文献信息

• Reductive coupling of α,β-enones I: Reduction of methyl-vinyl ketone and mesityl oxide.
  作者：Jean-Marc Pons、Jean-Pierre Zahra、Maurice Santelli

  DOI：10.1016/s0040-4039(01)82039-6

  日期：1981.1

  Reductive coupling of methyl-vinyl ketone with TiCl4-Mg gives pinacol (25%). According to the reducing agents, mesityl oxide yields 2,4,5,7-tetramethyl-octa-2,4,6-triene (with 4TiCl3-LialH4), triene or 2,4,5,7-tetramethyl-octa-2,6-dien-4,5-diol (with TiCl4-Mg), pinacol (with VCl3-Mg), and 2-acetyl-1,3,3,4,4-pentamethyl-cyclopentane (with CrCl3-Mg or FeCl3-Mg or ZrCl4 or ZrCl4-Mg) as major products

  甲基-乙烯基酮与TiCl 4 -Mg的还原偶联得到频哪醇（25％）。根据还原剂，异亚丙基丙酮产生2,4,5,7-四甲基-辛基-2,4,6-三烯（具有4TiCl 3 -LialH 4），三烯或2,4,5,7-四甲基-辛基-2,6-二烯-4,5-二醇（含TiCl 4 -Mg），频哪醇（含VCl 3 -Mg）和2-乙酰基-1,3,3,4,4-五甲基环戊烷（含CrCl 3 -Mg或FeCl 3 -Mg或ZrCl 4或ZrCl 4 -Mg）为主要产品。
• Unexpected Ti^III/Mn-Promoted Pinacol Coupling of Ketones
  作者：Miguel Paradas、Araceli G. Campaña、Rosa E. Estévez、Luis Álvarez de Cienfuegos、Tania Jiménez、Rafael Robles、Juan M. Cuerva、J. Enrique Oltra

  DOI：10.1021/jo9005238

  日期：2009.5.1

  Titanocene(III) chemistry has emerged in the last decades as an indispensable tool in C-C bond-forming reactions. In this context, pinacol and related reactions allow the stereoselective synthesis of vicinal diols. In this work, we present new applications of these reactions using as starting materials aromatic ketones. Simple and smooth reaction conditions have been developed and have been applied for inter- and intramolecular processes. We also describe that although Cp2TiCl is usually used as a monoelectronic reducing agent, it can be also used as an efficient Lewis acid.
• PONS J.-M.; ZAHRA J.-P.; SANTELLI M., TETRAHEDRON LETT., 1981, 22, NO 40, 3965-3968
  作者：PONS J.-M.、 ZAHRA J.-P.、 SANTELLI M.

  DOI：——

  日期：——