(2S,3S,5E)-2,3-oxirane-6-phenylhex-5-en-1-ol | 678148-77-1

• 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: (2S,3S,5E)-2,3-oxirane-6-phenylhex-5-en-1-ol
• 英文别名: [(2S,3S)-3-[(E)-3-phenylprop-2-enyl]oxiran-2-yl]methanol
• CAS: 678148-77-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: LSQRURXEXSMLJE-XTPCBIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,5E)-2,3-oxirane-6-phenylhex-5-en-1-ol 在 titanium(IV) isopropylate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 ((2S,3R,5R,6S)-3-Isopropoxy-6-phenyl-5-phenylselanyl-tetrahydro-pyran-2-yl)-methanol
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification

  摘要：

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.

  DOI：

  10.3987/com-03-9959
• 作为产物：
  描述：

  (2E,5E)-6-phenyl-2,5-hexadien-1-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 四正丁基氢氧化膦 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以71%的产率得到(2S,3S,5E)-2,3-oxirane-6-phenylhex-5-en-1-ol
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification

  摘要：

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.

  DOI：

  10.3987/com-03-9959

文献信息

• Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification
  作者：Michelangelo Gruttadauria、Carmela Aprile、Paolo Lo Meo、Serena Riela、Renato Noto

  DOI：10.3987/com-03-9959

  日期：——

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.