(1S,3S,4S,5S)-3-phenyl-5-phenylselenyl-hexahydro-benzo[1,4]dioxin-2-one | 849596-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (1S,3S,4S,5S)-3-phenyl-5-phenylselenyl-hexahydro-benzo[1,4]dioxin-2-one
• 英文别名: (3S,4aS,5S,8aS)-3-phenyl-5-phenylselanyl-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxin-2-one
• CAS: 849596-58-3
• 化学式: C₂₀H₂₀O₃Se
• 分子量: 387.337
• InChiKey: SSSZPACCWSIPHJ-VJANTYMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,5S)-3-phenyl-5-phenylselenyl-hexahydro-benzo[1,4]dioxin-2-one 在 palladium dihydroxide 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium osmate(VI) 、 sodium periodate 、 TEA 、 氢气 、 二甲基二环氧乙烷 、 sodium hydride 、 碳酸氢钠 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 四氯化碳 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 86.5h， 生成 3-deoxy-epi-inositol
  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)-cyclohex-2-enyl hydroxy(phenyl)acetate 、 N-(苯硒基)邻苯二甲酰亚胺 在 三氟化硼乙醚 作用下， 反应 0.33h， 以33%的产率得到(1S,3S,4S,5S)-3-phenyl-5-phenylselenyl-hexahydro-benzo[1,4]dioxin-2-one
  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

文献信息

• Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources
  作者：Yong Joo Lee、Kyunghoon Lee、Sea Ill Jung、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1016/j.tet.2005.01.003

  日期：2005.2

  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.