(1S,2S,5S,6S)-4-bromo-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-ene-1-ol | 1215209-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,5S,6S)-4-bromo-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-ene-1-ol
• 英文别名: (3aS,4S,5S,7aS)-7-bromo-2,2-dimethyl-5-phenylselanyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 1215209-54-3
• 化学式: C₁₅H₁₇BrO₃Se
• 分子量: 404.162
• InChiKey: OKSKSFRTJITMHX-DGAVXFQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (1S,2S,5S,6S)-4-bromo-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-ene-1-ol 在 水 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以70%的产率得到(1S,2S,3S,6S)-4-bromo-6-(phenylselenyl)cyclohex-4-ene-1,2,3-triol
  参考文献：
  名称：

  Novel deoxy-selenylconduritols: chemoenzymatic synthesis and biological evaluation

  摘要：

  The first synthesis of two selenyldeoxycyclitols (4-bromo-2-phenylselenyl conduritol F and 6-phenylselenylconduritol F) is reported via a chemoenzymatic enantioselective route. The key step of the synthesis is the selenolysis of a vinyl epoxide. The new compounds were evaluated for their capacity to inhibit the growth of different microorganisms using a modification of the agar diffusion technique with thin layer chromatography plates as support. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.004
• 作为产物：
  描述：

  二苯基二硒醚 、 [3aS-(3aα,5aβ,6aβ,6bα)]-4-溴-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烷并[e]-1,3-苯并二茂 在 sodium tetrahydroborate 、 氯化铵 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 1.0h， 以89%的产率得到(1S,2S,5S,6S)-4-bromo-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-ene-1-ol
  参考文献：
  名称：

  Novel deoxy-selenylconduritols: chemoenzymatic synthesis and biological evaluation

  摘要：

  The first synthesis of two selenyldeoxycyclitols (4-bromo-2-phenylselenyl conduritol F and 6-phenylselenylconduritol F) is reported via a chemoenzymatic enantioselective route. The key step of the synthesis is the selenolysis of a vinyl epoxide. The new compounds were evaluated for their capacity to inhibit the growth of different microorganisms using a modification of the agar diffusion technique with thin layer chromatography plates as support. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.004