2,3-diphenylbutane-1,4-diol | 6583-62-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,3-diphenylbutane-1,4-diol
• CAS: 6583-62-6
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: RODMSFOPKZGWIX-UHFFFAOYSA-N

物化性质

• 熔点：
  148-148.5 °C
• 沸点：
  180-200 °C(Press: 2 Torr)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-diphenylbutane-1,4-diol 、 对甲苯磺酰氯 在 吡啶 作用下， 以85%的产率得到[4-(4-Methylphenyl)sulfonyloxy-2,3-diphenylbutyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Convenient Methods for Synthesis of C2-Symmetric Diphenyltetrahydro­thiophenes

  摘要：

  通过在关键步骤中使用易于处理的硼烷体系四丁基硼氢化铵-碘和四丁基铵-氨，合成了外消旋和光学纯的 (-)-(3R,4R)-3,4-二苯基四氢噻吩、(+)-(2S,5S)-2,5-二苯基四氢噻吩和 (-)-(3S,6S)-3,6-二苯基-1、2-dithiane 的合成，在关键步骤中使用了易于处理的硼烷体系四丁基硼氢化铵-碘和四丁基硼氢化铵-碘甲烷。

  DOI：

  10.1055/s-0028-1088123
• 作为产物：
  描述：

  氧化苯乙烯 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到2,3-diphenylbutane-1,4-diol
  参考文献：
  名称：

  Novel Reductive Cleavage Reaction of α-Halo Epoxides with SMI₂: Synthesis of Cyclopropanols

  摘要：

  在 HMPA 存在的情况下，芳基取代的 δ-halo 环氧化物与 SmI2 反应生成环丙醇，而在 HMPA 不存在的情况下生成烯丙醇。

  DOI：

  10.1055/s-1998-1889

文献信息

• Radical Titanocene Promoted Coupling of Epoxides and Vinyl Sulfones
  作者：Alfonso Fernández-Mateos、Soledad Encinas-Madrazo、Pablo Herrero-Teijón、Rosa Rubio González

  DOI：10.1002/ejoc.201403288

  日期：2015.1

  A radical coupling reaction of diverse vinyl sulfones and epoxides was mediated by Cp2TiCl (Cp = cyclopentadienyl) to provide a straightforward synthetic pathway to hydroxy sulfones. The reaction was successfully achieved by using either an excess or a catalytic amount of the TiIII reagent. The scope of the reaction was studied for several different functionalized and substituted epoxides and vinyl

  多种乙烯基砜和环氧化物的自由基偶联反应由 Cp2TiCl（Cp = 环戊二烯基）介导，以提供直接合成羟基砜的途径。通过使用过量或催化量的 TiIII 试剂成功地实现了反应。对几种不同的官能化和取代的环氧化物和乙烯基砜的反应范围进行了研究。
• Reactions of oxiranes with alkali metals: intermediacy of radical-anions
  作者：K.N. Gurudutt、M.A. Pasha、B. Ravindranath、P. Srinivas

  DOI：10.1016/s0040-4020(01)91816-2

  日期：1984.1

  Reaction of oxiranes with alkali metals in aprotic solvents yields a variety of products depending on the nature of the metal and the structure of the oxirane. Deoxygenation to olefins is the major reaction in case of lithium. Rearrangement to carbonyl compounds, reduction to alcohols and formation of dimeric products occur when oxiranes are treated with sodium. All the reactions could be rationalised

  在非质子传递溶剂中环氧乙烷与碱金属的反应产生各种产物，具体取决于金属的性质和环氧乙烷的结构。在锂的情况下，脱氧为烯烃是主要反应。当用钠处理环氧乙烷时，会发生羰基化合物的重排，醇的还原和二聚产物的形成。所有反应都可以通过一种机制进行合理化处理，该机制涉及初始的单个电子转移，从而导致自由基阴离子中间体的形成。
• Control of Homocoupling Versus Reduction in Titanium(III)-Mediated Radical Opening of Styrene Oxides
  作者：José A. González-Delgado、Jesús F. Arteaga

  DOI：10.1002/ejoc.201901625

  日期：2019.12.31

  Titanocene monochloride mediates the homolytic opening of styrene oxides in a chemoselectively controlled manner, leading either to homocoupling products or to phenethyl alcohol derivatives. Remarkably this protocol encompasses the diverse reactivity pattern of styrene oxides towards the desired products, thereby adding value to this interesting building block.

  钛新世一氯化物以化学选择性控制的方式介导苯乙烯氧化物的均相开口，从而导致均偶联产物或苯乙醇衍生物。值得注意的是，该方案涵盖了苯乙烯氧化物对所需产品的多种反应模式，从而为这一令人感兴趣的构件增加了价值。
• Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides
  作者：Laura A. Brozek、Michael J. Ardolino、James P. Morken

  DOI：10.1021/ja2075967

  日期：2011.10.26

  Palladium-catalyzed allyl-ally cross-coupling was investigated with substituted prochiral allylic boronates. These reactions deliver products bearing adjacent stereocenters, and the issue of diastereocontrol is therefore paramount. Under appropriately modified conditions, this allyl allyl coupling strategy was found to apply to a range of substrates, generally occurring with high enantioselectivity (92:8 to >99:1 er) and good diastereoselection (4:1 to 14:1 dr).
• Titanocene-Promoted Intermolecular Couplings of Epoxides with Nitriles. An Easy Access to β-Hydroxyketones
  作者：A. Fernández-Mateos、S. Encinas Madrazo、P. Herrero Teijón、R. Rubio González

  DOI：10.1021/jo900479v

  日期：2009.5.15

  Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of beta-hydroxyketones. The conditions of this "aldol-like" reaction are mild enough to avoid the dehydration of the beta-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.