1,2-二-4-联苯基-1,2-乙二醇 | 86130-04-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,2-二-4-联苯基-1,2-乙二醇
• 英文名称: 1,2-di-4-biphenyl-1,2-ethanediol
• 英文别名: 1,2-Di(biphenyl-4-yl)ethane-1,2-diol；1,2-bis(4-phenylphenyl)ethane-1,2-diol
• CAS: 86130-04-3
• 化学式: C₂₆H₂₂O₂
• 分子量: 366.459
• InChiKey: HRKLEAARYLSDSO-UHFFFAOYSA-N

物化性质

• 沸点：
  578.5±50.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1,2-二-4-联苯基-1,2-乙二醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 1,2-二-1,1''-联苯-4-基乙烷-1,2-二酮
  参考文献：
  名称：

  Synthesis of Ferrocene Derivatives with Planar Chirality via Palladium-Catalyzed Enantioselective C–H Bond Activation

  摘要：

  The first catalytic and enantioselective C-H direct acylation of ferrocene derivative has been developed A series of 2-acyl-1-dimethylaminomethylferrocenes with planar chirality were provided under highly efficient and concise one-pot condition with up to 85% yield and 98% ee. The products obtained could be easily converted to various chiral ligands via diverse trans formations.

  DOI：

  10.1021/ol502509f
• 作为产物：
  描述：

  联苯-4-甲醇 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以20%的产率得到1,2-二-4-联苯基-1,2-乙二醇
  参考文献：
  名称：

  Use of 4-biphenylmethanol, 4-biphenylacetic acid and 4-biphenylcarboxylic acid/triphenylmethane as indicators in the titration of lithium alkyls. Study of the dianion of 4-biphenylmethanol

  摘要：

  DOI：

  10.1021/jo00163a038

文献信息

• Application of coumarin dyes for organic photoredox catalysis
  作者：Andrea Gualandi、Giacomo Rodeghiero、Emanuele Della Rocca、Francesco Bertoni、Marianna Marchini、Rossana Perciaccante、Thomas Paul Jansen、Paola Ceroni、Pier Giorgio Cozzi

  DOI：10.1039/c8cc04048f

  日期：——

  Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(III)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins

  在这里，我们报告易于制备和可用的香豆素染料在光氧化还原催化中的应用，它们能够模拟强大的还原剂[Ir（III）]配合物。在Et 3 N作为牺牲还原剂的情况下，香豆素衍生物9和10在频哪醇偶联和其他反应中用作光还原剂。由于香豆素的电子，光物理和空间性质可以改变，因此可以预测对几类光氧化还原反应的广泛适用性。
• Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide
  作者：Shintaro Okumura、Yasuhiro Uozumi

  DOI：10.1021/acs.orglett.1c02592

  日期：2021.9.17

  We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic

  我们开发了一种新的羰基化合物光催化聚合反应，以生成阴离子甲醇合成子。芳香醛或酮在铱光催化剂和 1,3-二甲基-2-苯基-2,3-二氢-1 H-苯并咪唑 (DMBI) 作为还原剂的存在下与二氧化碳反应，在可见光照射下提供通过将所得的甲醇阴离子与亲电二氧化碳进行亲核加成，生成相应的α-羟基羧酸。
• Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions
  作者：Simone Potenti、Andrea Gualandi、Alessio Puggioli、Andrea Fermi、Giacomo Bergamini、Pier Giorgio Cozzi

  DOI：10.1002/ejoc.202001640

  日期：2021.3.19

  Green Photoredox! Negligibly toxic bismuth salts can be employed in a photoredox allylation of aldehydes mediated by an organic dye. To further add interest to this new methodology, the photoredox Barbier allylation is carried out in EtOH/water and shows low sensitivity to oxygen and radical scavengers.

  绿色Photoredox！毒性极低的铋盐可用于有机染料介导的醛的光氧化还原烯丙基化。为了进一步增加对这种新方法的兴趣，光氧化还原巴比尔烯丙基化反应在EtOH /水中进行，对氧气和自由基清除剂的敏感性较低。
• The First Catalytic Enantioselective Nozaki-Hiyama Reaction
  作者：Marco Bandini、Pier Giorgio Cozzi、Paolo Melchiorre、Achille Umani-Ronchi

  DOI：10.1002/(sici)1521-3773(19991115)38:22<3357::aid-anie3357>3.0.co;2-w

  日期：1999.11.15

  The Nozaki-Hiyama reaction can be performed in an enantioselective catalytic way! The catalytic system utilizes 10 mol % of an inexpensive chiral [Cr(salen)] complex. The [Cr(salen)]/Mn/Me(3)SiCl system effectively promotes the enantioselective addition of allyl chloride to aliphatic and aromatic aldehydes at room temperature (65-89 % ee, 40-60 % yield).

  Nozaki-Hiyama反应可以对映选择性催化方式进行！催化系统利用10 mol％的廉价手性[Cr（salen）]配合物。[Cr（salen）] / Mn / Me（3）SiCl系统可在室温下（65-89％ee，40-60％的收率）有效地促进烯丙基氯向脂族和芳族醛的对映选择性加成。
• Photocatalytic Cross‐Pinacol Coupling Promoted by Carbon Dioxide**
  作者：Shintaro Okumura、Teruki Takahashi、Kaoru Torii、Yasuhiro Uozumi

  DOI：10.1002/chem.202300840

  日期：2023.8.4

  A first photocatalytic cross-pinacol coupling was achieved. The reaction proceeded with a various combination of two aldehydes, two ketones, or an aldehyde and a ketone to afford the corresponding unsymmetric vicinal 1,2-diols in up to 91 % yield. In this process, an umpoled anionic carbinol synthon was generated in situ, by the assistance of CO2 additive, to react nucleophilically with a second electrophilic

  首次实现了光催化交叉频哪醇偶联。该反应以两种醛、两种酮或醛和酮的各种组合进行，以高达 91% 的产率提供相应的不对称邻位 1,2-二醇。在此过程中，在 CO 2添加剂的帮助下，原位生成了反极性的阴离子甲醇合成子，与第二个亲电子羰基化合物发生亲核反应。二氧化碳促进的光催化交叉频哪醇偶联（S. Okumura、Y. Uozumi 等）等）