(+/-)(2SR,4SR,1'SR)-4-hydroxy-2-(1'-phenylsulphanylpentyl)-tetrahydrofuran

• 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,4SR,1'SR)-4-hydroxy-2-(1'-phenylsulphanylpentyl)-tetrahydrofuran
• 英文别名: (3R,5R)-5-[(1R)-1-phenylselanylpentyl]oxolan-3-ol
• 化学式: C₁₅H₂₂O₂Se
• 分子量: 313.298
• InChiKey: FOYQUDOEUNPFSX-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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,4SR,1'SR)-4-hydroxy-2-(1'-phenylsulphanylpentyl)-tetrahydrofuran 在 高氯酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (+/-)(2SR,3SR,5SR)-2-butyl-3-phenylselanyl-tetrahydropyran-5-ol 、 (+/-)(2RS,3RS,5SR)-2-butyl-3-phenylselanyl-tetrahydropyran-5-ol
  参考文献：
  名称：

  Kinetic and thermodynamic control in the intramolecular hydroxyl capture of seleniranium ions

  摘要：

  The formation of tetrahydrofurans and tetrahydropyrans by acid catalyzed cyclization of hydroxy selenides can be explained by kinetic and thermodynamic control. The tetrahydropyrans from the hybrid 7-endo/6-exo cyclization are the thermodynamic products of the acid catalyzed cyclization of hydroxy selenides 1, whereas the tetrahydrofurans from the 5-exo cyclization are the kinetic products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01779-7
• 作为产物：
  描述：

  (2R,4S,5S)-5-Phenylselanyl-nonane-1,2,4-triol 在 高氯酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 生成 (+/-)(2RS,4SR,1'RS)-4-hydroxy-2-(1'phenylsulphanylpentyl)-tetrahydrofuran 、 (+/-)(2SR,4SR,1'SR)-4-hydroxy-2-(1'-phenylsulphanylpentyl)-tetrahydrofuran
  参考文献：
  名称：

  Kinetic and thermodynamic control in the intramolecular hydroxyl capture of seleniranium ions

  摘要：

  The formation of tetrahydrofurans and tetrahydropyrans by acid catalyzed cyclization of hydroxy selenides can be explained by kinetic and thermodynamic control. The tetrahydropyrans from the hybrid 7-endo/6-exo cyclization are the thermodynamic products of the acid catalyzed cyclization of hydroxy selenides 1, whereas the tetrahydrofurans from the 5-exo cyclization are the kinetic products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01779-7

文献信息

• The question of exo vs endo cyclisation. A joint experimental and ab initio study on the stereoselective synthesis of tetrahydrofurans and tetrahydropyrans via seleniranium ions
  作者：Michelangelo Gruttadauria、Paolo Lo Meo、Renato Noto

  DOI：10.1016/s0040-4020(00)01154-6

  日期：2001.2

  The reactivity of hydroxy selenides with catalytic amounts of perchloric acid in dichloromethane was investigated. Four different cyclisation modes (4-exo, 5-endo, 5-exo and 6-endo) of the intermediate seleniranium ion could occur. The reaction of the hydroxy selenides with primary and secondary hydroxyl groups in the same side chain led first to a mixture of tetrahydrofurans from the 5-exo cyclisation (kinetic products), then to a 68/32 mixture of tetrahydropyrans from the 6-endo cyclisation (thermodynamic products) probably via two diasteromeric seleniranium ions. Both experimental and ab initio (HF/3-21G*) studies showed that the order of cyclisation of the intermediate seleniranium ion was 5-exo-tet<6-wndo-tet<5-enda-tet<4-exo-tet. The factors on which regiochemistry of the 4-exo vs the 5-endo cyclisation and the 5-exo vs the 6-endo cyclisation of the seleniranium ions depend were analysed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Kinetic and thermodynamic control in the intramolecular hydroxyl capture of seleniranium ions
  作者：Michelangelo Gruttadauria、Renato Noto

  DOI：10.1016/s0040-4039(99)01779-7

  日期：1999.11

  The formation of tetrahydrofurans and tetrahydropyrans by acid catalyzed cyclization of hydroxy selenides can be explained by kinetic and thermodynamic control. The tetrahydropyrans from the hybrid 7-endo/6-exo cyclization are the thermodynamic products of the acid catalyzed cyclization of hydroxy selenides 1, whereas the tetrahydrofurans from the 5-exo cyclization are the kinetic products. (C) 1999 Elsevier Science Ltd. All rights reserved.