(1R,2R)-1-phenylbut-3-ene-1,2-diol | 145376-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-1-phenylbut-3-ene-1,2-diol
• CAS: 145376-17-6
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: WIVMOHUVHFHFLN-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (1R,2R)-1-phenylbut-3-ene-1,2-diol 在 双(乙腈)氯化钯(II) 4-二甲氨基吡啶 、 AD-mix-β 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 7,8-di-O-acetyl-goniodiol
  参考文献：
  名称：

  A Short and General Approach to the Synthesis of Styryllactones:(+)-Goniodiol, its Acetates and β-Trifluoromethyl Derivative, (+)-7-epi-Goniodiol and (+)-9-Deoxygoniopypyrone

  摘要：

  (+)-Goniodiol 及其醋酸盐和δ-三氟甲基衍生物、(+)-7-epi-Goniodiol 和 (+)-9-deoxygoniopypyrone 是苯乙烯内酯的代表，这些化合物已通过简短而通用的方法合成。关键步骤包括环状烯丙基碳酸酯与乙烯基三丁基锡的区域选择性不对称二羟基化和钯催化交叉耦合。

  DOI：

  10.1055/s-2002-32977
• 作为产物：
  描述：

  在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 12.0h， 以25.1 mg的产率得到(1R,2R)-1-phenylbut-3-ene-1,2-diol
  参考文献：
  名称：

  Enantio- and Diastereoselective Synthesis of (E)-1,5-syn-Diols: Application to the Synthesis of the C(23)−C(40) Fragment of Tetrafibricin

  摘要：

  A highly stereoselective synthesis of (E)-1,5-syn-diols 6 Is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 In 72-98% yields with > 95% ee and > 20:1 dr. Application of this method to the synthesis of the tetraflbricin C(23)-C(40) fragment 19 is described.

  DOI：

  10.1021/ol2003836

文献信息

• 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
  作者：Sergio Rossi、Tiziana Benincori、Laura Maria Raimondi、Maurizio Benaglia

  DOI：10.1055/s-0039-1690777

  日期：2020.4

  This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride)

  该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
• Enantioselective <i>syn</i>- and <i>anti</i>-Alkoxyallylation of Aldehydes via Brønsted Acid Catalysis
  作者：Shang Gao、Ming Chen

  DOI：10.1021/acs.orglett.8b02653

  日期：2018.10.5

  A diastereo- and enantioselective alkoxyallylation via phosphoric acid catalysis was reported. Under the developed conditions, either 1,2-syn- or 1,2-anti-alkoxyallylation adducts were obtained in good yields with high enantioselectivities.

  报道了通过磷酸催化的非对映和对映选择性烷氧基化。在发达的条件下，以高收率和高对映选择性获得1,2-顺-或1,2-抗烷氧基化加合物。
• A simple route to enantiomerically enriched oxazolidin-2-ones
  作者：Daqiang Xu、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)77462-4

  日期：1993.2

  The reaction of ene diols, which are readily available through catalytic asymmetric dihydroxylation of conjugated dienes, with p-tosylisocynate catalyzed by Pd(0) gave enantiomerically enriched oxazolidin-2-ones in high yields.

  烯二醇（可通过共轭二烯的催化不对称二羟基化反应轻松获得）与Pd（0）催化的对甲苯磺酰基异氰酸酯的反应可以高收率得到对映体富集的恶唑烷-2-酮。
• Asymmetric Synthesis of Trisubstituted Vicinal Diols through Copper(I)‐Catalyzed Diastereoselective and Enantioselective Allylation of Ketones with Siloxypropadienes
  作者：Nan Jiang、Pei‐Zhi Liu、Zhi‐Zhou Pan、Si‐Qing Wang、Qian Peng、Liang Yin

  DOI：10.1002/anie.202402195

  日期：——

  trisubstituted vicinal diols is accomplished by copper(I)-catalyzed diastereoselective and enantioselective reductive allylation of ketones with siloxypropadienes. The generation of both syn-diols and anti-diols is rationalized by DFT calculations, which show that cis-γ-siloxy-allyl copper species are generated favorably in the reduction of either 1-TBSO-propadiene or 1-TIPSO-propadiene by copper hydride

  三取代邻位二醇的不对称合成是通过铜(I) 催化的酮与甲硅烷氧基丙二烯的非对映选择性和对映选择性还原烯丙基化来完成的。通过DFT计算合理化了顺式二醇和反式二醇的生成，这表明顺式-γ-甲硅烷氧基-烯丙基铜物种在铜还原1-TBSO-丙二烯或1-TIPSO-丙二烯时有利地生成氢化物种类。
• Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: application to the synthesis of the C(23)–C(40) fragment of tetrafibricin
  作者：Philippe Nuhant、Jeremy Kister、Ricardo Lira、Achim Sorg、William R. Roush

  DOI：10.1016/j.tet.2011.06.008

  日期：2011.9

  Interest in the synthesis of the C(23) C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23) C(40) fragment 2 of tetrafibricin. (C) 2011 Elsevier Ltd. All rights reserved.