(2R,3R)-diphenyl-1,4-butanediol | 24568-35-2

• 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: (2R,3R)-diphenyl-1,4-butanediol
• 英文别名: (2R,3R)-(-)-2,3-diphenylbutane-1,4-diol；(-)-(2R,3R)-2,3-diphenyl-1,4-butanediol；(2R,3R)-diphenylbutane-1,4-diol；<2R.3R>-2.3-Diphenyl-butan-diol-(1.4)；(2R,3R)-2,3-diphenylbutane-1,4-diol
• CAS: 24568-35-2
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: RODMSFOPKZGWIX-HOTGVXAUSA-N

物化性质

• 熔点：
  100-101 °C(Solv: hexane (110-54-3))
• 沸点：
  392.1±37.0 °C(Predicted)
• 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：

  (2R,3R)-diphenyl-1,4-butanediol 生成 trans-(3R,4R)-diphenylpyrrolidine
  参考文献：
  名称：

  Novel 3,4-Diarylpyrrolidine-Based Chiral Ligands for the Asymmetric Reaction of Arylmagnesium Bromides with Aldehydes

  摘要：

  利用新型手性二胺配体，将芳基溴化镁不对称加成到醛上，得到相应的甲醇，其 ee 为 40-75%。

  DOI：

  10.1246/cl.1987.65
• 作为产物：
  描述：

  3,4-diphenylhexa-1,5-diene 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3R)-diphenyl-1,4-butanediol
  参考文献：
  名称：

  Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides

  摘要：

  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).

  DOI：

  10.1021/ja2075967

文献信息

• Iron-Catalyzed Ring-Closing C−O/C−O Metathesis of Aliphatic Ethers
  作者：Tobias Biberger、Szabolcs Makai、Zhong Lian、Bill Morandi

  DOI：10.1002/anie.201802563

  日期：2018.6.4

  Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring‐closing reactions. Herein, we report

  在迄今为止有机化学中已知的所有复分解反应中，诸如烯烃和炔烃之类的多个键的复分解已发展成为构建分子复杂性的最有效方法之一。相比之下，涉及单键的复分解反应很少，而且发展还很不充分，特别是在具有合成价值的闭环反应的情况下。在这里，我们报道了脂肪族醚的铁催化开环复分解反应，用于合成取代的四氢吡喃和四氢呋喃，以及吗啉和多环醚。这种转变是通过简单的铁催化剂实现的，并且可能会通过环状氧鎓中间体进行。
• Convenient Methods for Synthesis of C2-Symmetric Diphenyltetrahydro­thiophenes
  作者：Mariappan Periasamy、Gurubrahamam Ramani、Gopal Muthukumaragopal

  DOI：10.1055/s-0028-1088123

  日期：2009.5

  Racemic and optically pure (-)-(3R,4R)-3,4-diphenyltetrahydrothiophene, (+)-(2S,5S)-2,5-diphenyltetrahydrothiophene, and (-)-(3S,6S)-3,6-diphenyl-1,2-dithiane were synthesized by use, in the crucial steps, of the easy-to-handle borane systems tetra­butylammonium borohydride-iodine and tetrabutylammonium borohydride-iodomethane.

  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。
• Influence of β-arranged substituents in chiral seven-membered rhodium diphosphine rings on asymmetric hydrogenation of amino acid precursors
  作者：Hanswalter Krause、Cornelia Sailer

  DOI：10.1016/0022-328x(92)83120-7

  日期：1992.1

  Investigations concerning the optical induction in asymmetric hydrogenation reactions confirm the stereochemical control function of mono- and di-substituents in seven-membered chelate ring diphosphines, whereby the bulkiness of substituents in the backbone of the ligands is reflected in higher enantioselectivities.

  关于不对称氢化反应中的光诱导的研究证实了七元螯合环二膦中单取代基和二取代基的立体化学控制功能，由此配体主链中取代基的庞大反映在较高的对映选择性中。
• Absolute configurations of some 1,2-diphenylethane derivatives
  作者：N.D. Berova、B.J. Kurtev

  DOI：10.1016/s0040-4020(01)82780-0

  日期：1969.1

  The absolute configurations of two series of genetically related compounds with a general formula PhCH(X) - CH(Y)Ph are determined by chemical correlation with 2,3-diphenylpropanoic acid (V). It is demonstrated that all threo-isomers of absolute configuration A are laevorotatory and reasons are given that this is due to conformational asymmetry.

  通式为PhCH（X）-CH（Y）Ph的两个系列遗传相关化合物的绝对构型是通过与2,3-二苯基丙酸（V）的化学相关性确定的。证明了所有具有绝对构型A的苏式异构体都是立构的，并且给出了这是由于构象不对称的原因。
• Asymmetric C C bond formation by the mixed oxidative coupling of 1,1′-bi-2-naphthyl esters
  作者：Aurelio G. Csákÿ、M.Belén Mula、Myriam Mba、Joaquı́n Plumet

  DOI：10.1016/s0957-4166(02)00173-8

  日期：2002.5

  Asymmetric C-C bond formation was effected by the oxidative coupling of two different ester enolates using (R)-(+)-1,1'-bi(2-naphthol) as a common tether which served to link together both ester moieties in an asymmetric environment. Reduction of the corresponding succinates afforded diastereomerically pure 2,3-disubstituted-1,4-butanediols. (C) 2002 Published by Elsevier Science Ltd.