1,4-bis-(2-(S)-oxiranylmethoxy)benzene | 201477-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis-(2-(S)-oxiranylmethoxy)benzene
• 英文别名: (2S)-2-[[4-[[(2S)-oxiran-2-yl]methoxy]phenoxy]methyl]oxirane
• CAS: 201477-75-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: FSYPIGPPWAJCJG-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis-(2-(S)-oxiranylmethoxy)benzene 在 potassium osmate 、 lithium aluminium tetrahydride 、 正丁基锂 、 K₂OsO₂(OH)4,DHQ)2PHAL 、 三氟化硼乙醚 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二乙二醇二甲醚 、 水 、 叔丁醇 为溶剂， 反应 122.0h， 生成 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene
  参考文献：
  名称：

  Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

  摘要：

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.

  DOI：

  10.1021/jo971324h
• 作为产物：
  描述：

  1,4-二(丙-2-烯氧基)苯 在 氢溴酸 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 63.5h， 生成 1,4-bis-(2-(S)-oxiranylmethoxy)benzene
  参考文献：
  名称：

  Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

  摘要：

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.

  DOI：

  10.1021/jo971324h

文献信息

• Synthesis and Recognition Properties of Enantiomerically Pure Acyclic Cucurbit[<i>n</i>]uril-Type Molecular Containers
  作者：Xiaoyong Lu、Lyle Isaacs

  DOI：10.1021/acs.orglett.5b01948

  日期：2015.8.21

  Enantiomerically pure acyclic cucurbit[n]uril containers 1 and 2 were synthesized by the condensation of enantiomerically pure aromatic sidewalls 3b and 4b with glycoluril tetramer 5. Containers 1 and 2 are C2-symmetric, feature four arms of the same handedness, and bind to a variety of guests (6–15) in aqueous solution including aliphatic and aromatic ammonium ions, amino acids, dyes, and viologens

  对映体纯的无环葫芦[ n ] uril容器1和2是通过对映体纯的芳族侧壁3b和4b与甘脲四聚体5的缩合合成的。容器1和2是C 2对称的，具有四个相同手性的臂，并与水溶液中的各种来宾（6 – 15）结合，包括脂肪族和芳香族铵离子，氨基酸，染料和紫精。主体1 Ac和1 OH的结合常数通过1 H NMR和UV / vis光谱法测定对所选手性铵离子的离子。
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  DOI：10.1080/14756366.2024.2353711

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  作者：Gullapalli Kumaraswamy、Kukkadapu Ankamma、Arigala Pitchaiah

  DOI：10.1021/jo701724f

  日期：2007.12.1

  [Graphics]A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.
• Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6<i>S</i>,7<i>S</i>,9<i>R</i>,10<i>R</i>)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product
  作者：Zhi-Min Wang、Ming Shen

  DOI：10.1021/jo971324h

  日期：1998.3.1

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.