(2R,3S)-2-((S)-2-(benzyloxy)-3-methylpenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol | 1456889-05-6

• 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: (2R,3S)-2-((S)-2-(benzyloxy)-3-methylpenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol
• CAS: 1456889-05-6
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: NEUFGOYDPDNMIX-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-((S)-2-(benzyloxy)-3-methylpenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol 在 silver perchlorate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 38.0h， 以14%的产率得到
  参考文献：
  名称：

  Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes

  摘要：

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.026
• 作为产物：
  描述：

  在 四丁基氟化铵 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 21.0h， 生成 (2R,3S)-2-((S)-2-(benzyloxy)-3-methylpenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes

  摘要：

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.026

文献信息

• Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes
  作者：Yumie Suzuki、Ayano Kuwabara、Yasuhiro Koizumi、Yuji Mori

  DOI：10.1016/j.tet.2013.08.026

  日期：2013.10

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.