(1S,3S,4S,6R,7R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol | 849596-51-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,3S,4S,6R,7R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol
• 英文别名: (2S,3S,4aR,5R,8aS)-2,3-diphenyl-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-5-ol
• CAS: 849596-51-6
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: LAJICUQQBIWEBA-JAZQRGJZSA-N

物化性质

• 沸点：
  483.1±45.0 °C(predicted)
• 密度：
  1.189±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (1S,3S,4S,6R,7R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol 在 氢氧化钾 、 potassium osmate(VI) 、 sodium periodate 、 正丁基锂 、 silver trifluoromethanesulfonate 、 碳酸氢钠 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 102.67h， 生成 2,3-diphenyl-octahydro-benzo[1,4]dioxine-5,6,7,8-tetrol
  参考文献：
  名称：

  Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources

  摘要：

  Reaction of 3-bromocyclohexene with (SS)-hydrobenzoin and (S)-mandelic acid and subsequent intramolecular oxyselenenylation of the resulting allylic ethers followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefins, (1S,3S,4S,6R)-3,4-diphenylbicyclo[4,4,0]-2,5-dioxa-7-decene and (1S,3S,4R)-3-phenyl-4a,7,8,8a-tetrahydro-benzo[1,4]dioxan-2-one, respectively. Further stereoselective transformation of these cis-fused bicyclic olefins afforded the enantiopure cyclohexitols, muco-quercitol, D-chiro-inocitol and allo-inocitol. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.003
• 作为产物：
  描述：

  (1S,3S,4S,6R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以94%的产率得到(1S,3S,4S,6R,7R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol
  参考文献：
  名称：

  Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources

  摘要：

  Reaction of 3-bromocyclohexene with (SS)-hydrobenzoin and (S)-mandelic acid and subsequent intramolecular oxyselenenylation of the resulting allylic ethers followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefins, (1S,3S,4S,6R)-3,4-diphenylbicyclo[4,4,0]-2,5-dioxa-7-decene and (1S,3S,4R)-3-phenyl-4a,7,8,8a-tetrahydro-benzo[1,4]dioxan-2-one, respectively. Further stereoselective transformation of these cis-fused bicyclic olefins afforded the enantiopure cyclohexitols, muco-quercitol, D-chiro-inocitol and allo-inocitol. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.003