(1S,2S,5R,6S)-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-en-1-ol | 1215209-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,5R,6S)-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-en-1-ol
• 英文别名: (3aS,4S,5S,7aR)-2,2-dimethyl-5-phenylselanyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 1215209-57-6
• 化学式: C₁₅H₁₈O₃Se
• 分子量: 325.266
• InChiKey: ZLMKLXBWNZXSEE-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  19
• 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,5R,6S)-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-en-1-ol 在 ruthenium trichloride 、 sodium periodate 、 水 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 2.0h， 以30%的产率得到(1R*,4R*,5S*,6R*)-1,4-dihydroxy-5,6-(isopropylidenedioxy)-2-cyclohexene
  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 、 [3aR-(3aα,5aβ,6aβ,6bα)]-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烯并[e]-1,3-苯并间二氧杂环戊烯 在 sodium tetrahydroborate 、 氯化铵 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 以72%的产率得到(1S,2S,5R,6S)-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-en-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

文献信息

• Novel deoxy-selenylconduritols: chemoenzymatic synthesis and biological evaluation
  作者：Ana Bellomo、Ana Bertucci、Hélio Stefani、Álvaro Vázquez、David Gonzalez

  DOI：10.1016/j.tetasy.2009.11.004

  日期：2009.12

  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.