(2SR,3RS)-2-phenyltetrahydrofuran-3-ol

• 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: (2SR,3RS)-2-phenyltetrahydrofuran-3-ol
• 英文别名: (2S,3R)-2-phenyloxolan-3-ol
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: IVSJPOQKBYMUOG-ZJUUUORDSA-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2SR,3RS)-2-phenyltetrahydrofuran-3-ol 在 4-二甲氨基吡啶 、 (R)-methoxytrifluoromethylphenylacetyl chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到
  参考文献：
  名称：

  Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds

  摘要：

  The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.

  DOI：

  10.1021/ol302669q
• 作为产物：
  描述：

  (2S,3R)-tetrahydro-2-phenylfuran-3-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到(2SR,3RS)-2-phenyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds

  摘要：

  The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.

  DOI：

  10.1021/ol302669q

文献信息

• Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn
  作者：Kyungsoo Oh、William Eric Knabe

  DOI：10.1016/j.tet.2009.02.013

  日期：2009.4

  A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O–C/O–N/O–S bonds through a single electron transfer from zinc metal to the niobium–substrate complex

  使用亚化学计量量的由市售NbCl 5和锌粉原位生成的低价铌络合物，描述了对环氧化合物，亚砜和胺N-氧化物进行温和且简单的脱氧的方法。由于铌物种的高亲氧性，单价电子从锌金属转移到铌-底物络合物，使极化的O-C / O-N / O-S键还原性裂解，从而进行脱氧。相邻的自由基稳定基团的存在对环氧底物是有利的。但是，类似的前提条件不适用于亚砜和胺N-氧化物，在这些亚胺和N-胺胺中，各种底物均能以优异的产率有效地脱氧。
• Synthesis of tetrahydrofurans by regio- and stereoselective cyclization of epoxyalcohols using magnesium halide
  作者：Michinori Karikomi、Shigeru Watanabe、Yukino Kimura、Tadao Uyehara

  DOI：10.1016/s0040-4039(02)00042-4

  日期：2002.2

  A Nobel synthetic method for several tetrahydrofuran derivatives by intramolecular cyclization of epoxyalchols is described. The presence of a catalytic amount of magnesium halide altered the regio- and stereoselectivity of the cyclization reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds
  作者：Takuya Okada、Airi Shimoda、Tetsuro Shinada、Kazuhiko Sakaguchi、Yasufumi Ohfune

  DOI：10.1021/ol302669q

  日期：2012.12.21

  The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.