(3S,4R,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol | 732249-13-7

• 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: (3S,4R,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol
• 英文别名: (3S,4R,5R)-5-phenyl-4-prop-2-enyloxolan-3-ol
• CAS: 732249-13-7
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: RGUGOJLATFSMSG-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol 在 偶氮二异丁腈 、 三氟化硼乙醚 、 三苯基氢化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 (3aS,4R,6aS)-2-methyl-4-phenylhexahydrofuro[3,4-b]furan
  参考文献：
  名称：

  Synthesis of enantiomerically pure perhydrofuro[3,4-b]pyrans and perhydrofuro[3,4-b]furans

  摘要：

  Olefinic diols, prepared from (R)-(+)-2,2-diinetliyl-1,3-dioxolane-4-carboxaldehyde via olefination and hydrolysis, were converted into enantiomerically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophthalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyl-tributylstannane in the presence of AIBN. The selenium promoted cyclizalions of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the Off and the allyl groups are cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.009
• 作为产物：
  描述：

  三苯基苄基溴化膦 在 盐酸 、 正丁基锂 、 偶氮二异丁腈 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 (3S,4R,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis of enantiomerically pure perhydrofuro[3,4-b]pyrans and perhydrofuro[3,4-b]furans

  摘要：

  Olefinic diols, prepared from (R)-(+)-2,2-diinetliyl-1,3-dioxolane-4-carboxaldehyde via olefination and hydrolysis, were converted into enantiomerically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophthalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyl-tributylstannane in the presence of AIBN. The selenium promoted cyclizalions of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the Off and the allyl groups are cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.009

文献信息

• Synthesis of enantiomerically pure perhydrofuro[3,4-b]pyrans and perhydrofuro[3,4-b]furans
  作者：Marcello Tiecco、Lorenzo Testaferri、Luana Bagnoli、Raffaella Terlizzi、Andrea Temperini、Francesca Marini、Claudio Santi、Catalina Scarponi

  DOI：10.1016/j.tetasy.2004.05.009

  日期：2004.6

  Olefinic diols, prepared from (R)-(+)-2,2-diinetliyl-1,3-dioxolane-4-carboxaldehyde via olefination and hydrolysis, were converted into enantiomerically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophthalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyl-tributylstannane in the presence of AIBN. The selenium promoted cyclizalions of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the Off and the allyl groups are cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN. (C) 2004 Elsevier Ltd. All rights reserved.