((3R,5R)-5-(bromomethyl)-5-phenyltetrahydrofuran-3-yl)methanol | 1593266-11-5

• 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: ((3R,5R)-5-(bromomethyl)-5-phenyltetrahydrofuran-3-yl)methanol
• 英文别名: [(3R,5R)-5-(bromomethyl)-5-phenyloxolan-3-yl]methanol
• CAS: 1593266-11-5
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: XODBSGAACGOQSI-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  dimethyl 2-(2'-bromoallyl)malonate 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 甲烷磺酸 、 potassium carbonate 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 82.5h， 生成 ((3R,5R)-5-(bromomethyl)-5-phenyltetrahydrofuran-3-yl)methanol
  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

• 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。
• 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.
• Catalytic and enantioselective bromoetherification of olefinic 1,3-diols: mechanistic insight
  作者：Zhihai Ke、Chong Kiat Tan、Yi Liu、Keefe Guang Zhi Lee、Ying-Yeung Yeung

  DOI：10.1016/j.tet.2015.09.016

  日期：2016.5

  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.
• Catalytic Asymmetric Bromoetherification and Desymmetrization of Olefinic 1,3-Diols with <i>C</i>₂-Symmetric Sulfides
  作者：Zhihai Ke、Chong Kiat Tan、Feng Chen、Ying-Yeung Yeung

  DOI：10.1021/ja5029155

  日期：2014.4.16

  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).