(1RS,2RS,5RS)-1-[5-(4-methoxybenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol | 1152091-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1RS,2RS,5RS)-1-[5-(4-methoxybenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol
• 英文别名: (1R,2R,5R)-1-[5-(4-methoxybenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol
• CAS: 1152091-64-9
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: AGFJPHHQGRKHDF-BRWVUGGUSA-N

物化性质

• 沸点：
  417.6±20.0 °C(predicted)
• 密度：
  1.063±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1RS,2RS,5RS)-1-[5-(4-methoxybenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol 、 2-溴-6-甲氧基萘 在 tris-(dibenzylideneacetone)dipalladium(0) 、 双(2-二苯基磷苯基)醚 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以61%的产率得到(2R,2'R,5R,5'R)-5-(4-methoxybenzyl)-5'-(6-methoxynaphthalen-2-ylmethyl)octahydro-2,2'-bifuran
  参考文献：
  名称：

  Synthesis of Fused-Ring and Attached-Ring bis-Tetrahydrofurans via Pd-Catalyzed Carboetherification

  摘要：

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.

  DOI：

  10.1021/ol900594h
• 作为产物：
  描述：

  {(1R)-1-[(2R,5R)-5-(4-methoxybenzyl)tetrahydrofuran-2-yl]pent-4-enyloxy}(tert-butyl)dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(1RS,2RS,5RS)-1-[5-(4-methoxybenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol
  参考文献：
  名称：

  Synthesis of Fused-Ring and Attached-Ring bis-Tetrahydrofurans via Pd-Catalyzed Carboetherification

  摘要：

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.

  DOI：

  10.1021/ol900594h