2-(2-phenylallyl)propane-1,3-diol | 835880-17-6

• 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: 2-(2-phenylallyl)propane-1,3-diol
• 英文别名: 2-(2-Phenylprop-2-enyl)propane-1,3-diol
• CAS: 835880-17-6
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: CMRUOENZDPTSKK-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C
• 沸点：
  361.5±42.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-(2-phenylallyl)propane-1,3-diol 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(5-methyl-5-phenyltetrahydrofuran-3-yl)methanol
  参考文献：
  名称：

  Catalytic and enantioselective bromoetherification of olefinic 1,3-diols: mechanistic insight

  摘要：

  How can high enantioselectivity be achieved when the racemic background reaction proceeds at a rate comparable to that of the catalytic asymmetric reaction? We attempted to rationalize this counterin-tuitive observation by studying the effect of (1) catalyst structure, (2) temperature and addition sequence of components, (3) catalyst loading, and (4) Bronsted acid additives. In the course of our investigation, it was found that increasing the amount of catalyst used led to inhibition of the stoichiometric reaction. Olefinic 1,3-diol 1, 5 mol % of catalyst 3a, 1 equiv of MsOH, and NBS were added at low temperature in a specific sequence to provide the best performance for the enantioselective bromoetherification. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.016
• 作为产物：
  描述：

  dimethyl 2-(2'-bromoallyl)malonate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 potassium carbonate 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 34.5h， 生成 2-(2-phenylallyl)propane-1,3-diol
  参考文献：
  名称：

  Catalytic Asymmetric Bromoetherification and Desymmetrization of Olefinic 1,3-Diols with C₂-Symmetric Sulfides

  摘要：

  An enantioselective and highly diastereoselective bromoetherification and desymmetrization of olefinic 1,3-diols has been developed using a C-2-symmetric cyclic sulfide catalyst. This methodology has been successfully applied to the synthesis of the key intermediate of an orally active antifungal drug posaconazole (Noxafil).

  DOI：

  10.1021/ja5029155

文献信息

• Nucleophile-Selective Selenocyclizations
  作者：Shaista�S. Khokhar、Thomas Wirth

  DOI：10.1002/ejoc.200400526

  日期：2004.11

  Electrophilic cyclizations are one of the major strategies for cyclofunctionalizations of alkenes. Selective selenocyclizations can be performed by adjusting various factors in such reactions. The nature of the electrophile, the counterion, solvents, and external additives coordinating to the electrophilic species are used to control the course of such cyclizations with high degrees of efficiency.

  亲电环化是烯烃环官能化的主要策略之一。选择性硒环化可以通过调整此类反应中的各种因素来进行。亲电试剂的性质、抗衡离子、溶剂和与亲电物质配位的外部添加剂用于以高效率控制这种环化过程。我们的研究已经扩展到使用手性硒亲电试剂的立体选择性反应。
• Investigating the Enantiodetermining Step of a Chiral Lewis Base Catalyzed Bromocycloetherification of Privileged Alkenes
  作者：Scott Denmark、Dietrich Böse

  DOI：10.1055/s-0036-1590951

  日期：2018.3

  The development of catalytic, enantioselective halofunctionalizations of unactivated alkenes has made significant progress in recent years. However, the identification of generally applicable catalysts for wide range of substrates has yet to be realized. A detailed understanding of the reaction mechanism is essential to guide the formulation of a truly general catalyst. Herein, we present our investigations on the enantiodetermining step of a Lewis base catalyzed bromocycloetherification that provides important insights and design criteria.

  最近几年来，对于未活化烯烃的催化、对映选择性卤代功能化反应取得了显著进展。然而，尚未实现对广泛底物适用的通用催化剂的识别。对反应机理的详细理解对于指导真正通用催化剂的制定至关重要。在这里，我们介绍了我们对路易斯碱催化溴环氧烷化反应中的对映决定步骤的研究，提供了重要的见解和设计准则。
• Desymmetrizing Enantio- and Diastereoselective Selenoetherification through Supramolecular Catalysis
  作者：Jie Yang See、Hui Yang、Yu Zhao、Ming Wah Wong、Zhihai Ke、Ying-Yeung Yeung

  DOI：10.1021/acscatal.7b03510

  日期：2018.2.2

  cations rapidly interchange between olefinic partners. Recently, it has been demonstrated that Lewis bases, assisted by Brønsted acids, induce high levels of enantioselectivity in selenocyclization reactions. The Brønsted acid serves as an activator for the reaction. In this work, we demonstrate an asymmetric selenoetherification and desymmetrization of olefinic 1,3-diols, driven by a unique chiral

  硒代官能化用于引入芳基或烷基硒基部分，然后可以将其转化成其他官能团（例如烯烃和羰基）。但是，未活化的烯烃的不对称硒官能化通常难以实现，因为芳基和烷基硒化阳离子在烯烃配偶体之间迅速交换。最近，已证明在布朗斯台德酸的辅助下，路易斯碱在硒环化反应中诱导高水平的对映选择性。布朗斯台德酸作为反应的活化剂。在这项工作中，我们证明烯1,3-二醇的不对称selenoetherification和desymmetrization，由一个唯一的手性配对之间驱动Ç 2 -对称环状硒化物催化剂和手性布朗斯台德酸。所得的取代的四氢呋喃含有苯基硒醚手柄，可以转化为合成有用的结构单元。一系列实验和计算研究表明，该反应通过超分子催化途径进行。
• Selenocyclizations: Control by Coordination and by the Counterion
  作者：Shaista S. Khokhar、Thomas Wirth

  DOI：10.1002/anie.200352884

  日期：2004.1.23
• Indole-Catalyzed Bromolactonization in Lipophilic Solvent: A Solid–Liquid Phase Transfer Approach
  作者：Tao Chen、Thomas Jian Yao Foo、Ying-Yeung Yeung

  DOI：10.1021/acscatal.5b01182

  日期：2015.8.7

  We have developed a novel indole-catalyzed bromolactonization of olefinic acids. The reaction could be conducted in lipophilic solvent through a solid liquid phase transfer mechanism. This catalytic protocol has been applied to the synthesis of base-sensitive bromolactones.