(R)-4-bromo-4-((R)-tetrahydrofuran-2-yl)butan-1-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (R)-4-bromo-4-((R)-tetrahydrofuran-2-yl)butan-1-ol
• 英文别名: (4R)-4-bromo-4-[(2R)-oxolan-2-yl]butan-1-ol
• 化学式: C₈H₁₅BrO₂
• 分子量: 223.11
• InChiKey: IJDCQSKTQSNBGD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,5-环辛二烯 在 甲醇 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 sodium (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diylhydrogen-phosphate 、 双氧水 、 ortho-tungstic acid 作用下， 以 二氯甲烷 为溶剂， 生成 2-(1'-bromo-4'-hydroxybutyl)-tetrahydrofuran 、 (R)-4-bromo-4-((R)-tetrahydrofuran-2-yl)butan-1-ol
  参考文献：
  名称：

  Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions

  摘要：

  A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.

  DOI：

  10.1021/ol1028805

文献信息

• Synthesis of Chiral Heterocyclic <i>N</i> -Haloamides and -imides and Their Applications as Halogenating Agents and Mechanistic Probes
  作者：Ulrich Hennecke、Christian H. Müller、Constantin G. Daniliuc

  DOI：10.1002/ejoc.201601159

  日期：2017.1.18

  reports of chiral derivatives of the most common of these reagents such as N-halosuccinimides. Herein, we report the synthesis of new chiral N-halogenated amides and imide derivatives, which are easily accessible from inexpensive starting materials of the chiral pool. These new chiral halogenating agents were then applied as stoichiometric reagents in haloetherification reactions and as mechanistic probes

  N-卤代酰胺和-酰亚胺是标准的卤化剂，已用于自由基和亲电卤化反应。尽管它们有很多应用，但关于这些试剂中最常见的手性衍生物（如 N-卤代琥珀酰亚胺）的报道很少。在此，我们报告了新的手性 N-卤代酰胺和酰亚胺衍生物的合成，它们很容易从手性池的廉价起始材料中获得。这些新的手性卤化剂随后被用作卤醚化反应中的化学计量试剂和有机催化卤环化反应中的机械探针。
• Enantioselective Haloetherification by Asymmetric Opening of <i>meso</i>-Halonium Ions
  作者：Ulrich Hennecke、Christian H. Müller、Roland Fröhlich

  DOI：10.1021/ol1028805

  日期：2011.3.4

  A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.