(1R,2R)-1,2-di(furan-2-yl)ethane-1,2-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1R,2R)-1,2-di(furan-2-yl)ethane-1,2-diol
• 英文别名: (S,S)-(-)-1,2-di(2'-furyl)ethane-1,2-diol；(R,R)-1,2-di(furan-2-yl)ethane-1,2-diol；1,2-di(furan-2-yl)ethane-1,2-diol；(1R,2R)-1,2-bis(furan-2-yl)ethane-1,2-diol
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: PAGAJWBCCKFHIT-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2'-联糠醛 在 甲酸 、 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 三乙胺 作用下， 反应 2.0h， 以99%的产率得到
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 1,2-DI(FURAN-2-YL)ETHANE-1,2-DIOLS AND DERIVATES THEREOF
  [FR] PROCÉDÉ DE PRÉPARATION DE 1,2-DI(FURAN-2-YL)ÉTHANE-1,2-DIOLS OPTIQUEMENT ACTIFS ET DÉRIVÉS DE CEUX-CI

  摘要：

  这项发明涉及利用手性金属化合物作为催化剂和特定氢源，通过不对称转移氢化合成式（II）化合物或式（IV）化合物或二者的混合物，制备式（S，S）-（I）或替代式（R，R）-（I）的光学活性1,2-二醇的过程。

  公开号：

  WO2013135869A1

文献信息

• Truly Catalytic and Enantioselective Pinacol Coupling of Aryl Aldehydes Mediated by Chiral Ti(III) Complexes^†
  作者：A. Chatterjee、T. H. Bennur、N. N. Joshi

  DOI：10.1021/jo0342875

  日期：2003.7.1

  A variety of chiral Ti(IV) complexes were reduced in situ with zinc in acetonitrile. The resulting chiral Ti(III) complexes were found to catalyze the pinacol coupling reaction stereoselectively. The best results were obtained from the Ti-SALEN complex, which was found to be an efficient catalyst at 10 mol % concentration. Various aromatic aldehydes were coupled to obtain chiral hydrobenzoin derivatives

  各种手性Ti（IV）配合物在乙腈中用锌原位还原。发现所得的手性Ti（III）配合物立体选择性地催化频哪醇偶联反应。从Ti-SALEN配合物获得了最佳结果，该配合物被发现是浓度为10 mol％的有效催化剂。偶联各种芳族醛以获得具有高非对映选择性和对映选择性的手性氢安息香衍生物。提出了合理的机制，使反应的立体化学结果合理化。
• Stereoselective Synthesis of Optically Active Hydrobenzoins via Asymmetric Hydrogenation of Benzils with Ru(OTf)(TsDPEN)(η6-cymene) as the Pre-catalyst
  作者：Xiaofei Huang、Naikai Li、Zhicong Geng、Fengfeng Pan、Xingwang Wang

  DOI：10.1002/cjoc.201200393

  日期：2012.8.14

  Optically active hydrobenzoins are very important building blocks for further derivation of biologically active complexes, natural products, and pharmaceutical compounds. In this paper, A practical approach has been developed for asymmetric hydrogenation of benzils with Ru(OTf)(TsDPEN)(η6‐cymene) as a pre‐catalyst in methanol. Therefore, a series of chiral hydrobenzoins was synthesized in good yields

  光学活性氢安息香素是进一步衍生生物活性复合物，天然产物和药物化合物的重要组成部分。在本文中，一个实用的方法已被用于与钌苯偶酰的不对称氢化显影（OTF）（TsDPEN）（η 6 -cymene）作为在甲醇中的预催化剂。因此，以良好的产率合成了一系列手性的氢安息香素，具有良好至中等的非对映选择性和良好至优异的对映选择性。
• Biomass Conversion to High Value Chemicals: From Furfural to Chiral Hydrofuroins in Two Steps
  作者：Anzhelika Kabro、Eduardo C. Escudero-Adán、Vladimir V. Grushin、Piet W. N. M. van Leeuwen

  DOI：10.1021/ol3018402

  日期：2012.8.3

  Catalytic asymmetric transfer hydrogenation of rac-furoin and furil produces hydrofuroin with up to 99% ee and 9:1 dr. This reaction provides an exceptionally easy access to optically active hydrofuroins in two straightforward steps from biomass-derived furfural (global production 200 000-300 000 t annually) using benzoin condensation.
• Stereoselective Reduction of Benzils:  A New Convenient Route to Enantiomerically Pure 1,2-Diarylethanediols
  作者：K. R. K. Prasad、N. N. Joshi

  DOI：10.1021/jo952017j

  日期：1996.1.1
• Enantioselective pinacol coupling reaction of aromatic aldehydes catalyzed by chiral vanadium complexes
  作者：Jiangtao Sun、Zhenya Dai、Changsi Li、Xu Pan、Chengjian Zhu

  DOI：10.1016/j.jorganchem.2009.06.030

  日期：2009.9

  The asymmetric pinacol coupling of aromatic aldehydes by chiral salan-vanadium complexes as effective catalysts is reported. Chiral 1,2-diols were obtained with high diastereoselectivities (up to 90/10) and moderate to high enantioselectivities (up to 82% ee). The possible mechanism of the pinacol coupling reaction is also discussed. (C) 2009 Elsevier B. V. All rights reserved.