4-phenylbutane-1,2,4-triol | 943621-73-6

• 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: 4-phenylbutane-1,2,4-triol
• 英文别名: 4-Phenylbutane-1,2,4-triol
• CAS: 943621-73-6
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: DHURKUJTEAIZJM-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±42.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenylbutane-1,2,4-triol 在 盐酸 、 sodium periodate 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 43.5h， 生成 1-phenylhex-5-ene-1,3-diol
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans

  摘要：

  An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.

  DOI：

  10.1021/acs.joc.5b02371
• 作为产物：
  描述：

  1-苯基-3-丁烯-1-醇 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以91%的产率得到4-phenylbutane-1,2,4-triol
  参考文献：
  名称：

  金催化的烯键式酰胺的环异构化

  摘要：

  1，6-烯-酰胺的金催化的环异构化在温和的条件下进行，并从末端或三甲基甲硅烷基取代的酰胺中产生环丁酮，或从具有炔丙醇部分的底物上产生带有2,3-甲基吡咯烷亚基的羰基化合物。用在氮原子的α或β位置具有立体中心的1，6-烯-酰胺具有高的非对映选择性。

  DOI：

  10.1016/j.tet.2008.10.108

文献信息

• Gold-catalyzed cycloisomerizations of ene-ynamides
  作者：Sylvain Couty、Christophe Meyer、Janine Cossy

  DOI：10.1016/j.tet.2008.10.108

  日期：2009.2

  The gold-catalyzed cycloisomerizations of 1,6-ene-ynamides proceed under mild conditions and lead to cyclobutanones from terminal or trimethylsilyl substituted ynamides, or to carbonyl compounds bearing a 2,3-methanopyrrolidine subunit from substrates possessing a propargylic alcohol moiety. High diastereoselectivities are observed with 1,6-ene-ynamides having a stereocenter at the α or β position

  1，6-烯-酰胺的金催化的环异构化在温和的条件下进行，并从末端或三甲基甲硅烷基取代的酰胺中产生环丁酮，或从具有炔丙醇部分的底物上产生带有2,3-甲基吡咯烷亚基的羰基化合物。用在氮原子的α或β位置具有立体中心的1，6-烯-酰胺具有高的非对映选择性。
• Transformation of homoallylic alcohol oxides into 3-hydroxytetrahydrofurans in aqueous HClO4
  作者：M. V. Chirskaya、A. A. Vasil’ev、S. V. Shorshnev、S. I. Sviridov

  DOI：10.1007/s11172-006-0415-8

  日期：2006.7

  Hydrolysis of allyl carbinol oxides in aqueous HClO4 gave the corresponding 1,2,4-triols. On heating in the same reaction medium, they underwent cyclization into 3-hydroxytetrahydrofurans. The method is restricted to substrates that can generate stable carbocations via elimination of the hydroxy group from position 4 in intermediate 1,2,4-triols.

  烯丙基甲醇氧化物在 HClO4 水溶液中水解得到相应的 1,2,4-三醇。在相同的反应介质中加热时，它们环化成 3-羟基四氢呋喃。该方法仅限于可通过消除中间体 1,2,4-三醇中 4 位羟基而产生稳定碳正离子的底物。
• The Nature of the Catalytically Active Species in Olefin Dioxygenation with PhI(OAc)₂: Metal or Proton?
  作者：Yan-Biao Kang、Lutz H. Gade

  DOI：10.1021/ja110805b

  日期：2011.3.16

  Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)(2) as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.
• Fournier, Bulletin de la Societe Chimique de France, 1895, vol. <3> 13, p. 121
  作者：Fournier

  DOI：——

  日期：——
• Green Organocatalytic Dihydroxylation of Alkenes
  作者：Alexis Theodorou、Ierasia Triandafillidi、Christoforos G. Kokotos

  DOI：10.1002/ejoc.201601144

  日期：2017.3.17

  A cheap, green and metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 was employed as the oxidant and 2,2,2-trifluoroacetophenone as the organocatalyst, leading to a highly sustainable protocol, where a variety of homoallylic alcohols, amino-alkenes and double bonds were converted into the corresponding polyalcohols in high to excellent yields. This manifold takes advantage

  描述了一种用于烯烃二羟基化的廉价、绿色和无金属的一锅法。使用 H2O2 作为氧化剂，使用 2,2,2-三氟苯乙酮作为有机催化剂，形成了一种高度可持续的方案，其中各种高烯丙醇、氨基烯烃和双键以高产率转化为相应的多元醇。该歧管利用环氧化反应，然后对反应混合物进行原位酸处理，水环打开三元环，产生所需的产物。