(1S,2R,3R,6S)-2,3-isopropylidendioxy-6-(phenylsulfinyl)cyclohex-4-ene-1-ol | 1115304-56-7

• 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: (1S,2R,3R,6S)-2,3-isopropylidendioxy-6-(phenylsulfinyl)cyclohex-4-ene-1-ol
• 英文别名: (3aS,4S,5S,7aR)-5-(benzenesulfinyl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 1115304-56-7
• 化学式: C₁₅H₁₈O₄S
• 分子量: 294.372
• InChiKey: CLDHEBMGFVZJPV-WZSURQGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  75
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,2R,3R,6S)-6-(phenylthio)-2,3-isopropylidendioxycyclohex-4-en-1-ol 在 叔丁基过氧化氢 、 ruthenium trichloride 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.5h， 以13%的产率得到(1S,2R,3R,6S)-2,3-isopropylidendioxy-6-(phenylsulfinyl)cyclohex-4-ene-1-ol
  参考文献：
  名称：

  Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols

  摘要：

  The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-1-chiro-inositol and deoxythio-cyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequence of enzymatic and ruthenium-catalyzed dihydroxylations, and the results were studied regarding reaction conditions and co-catalyst for different derivatives. The new compounds were included in a minilibrary of deoxygenated cyclitols and evaluated for their capacity to influence the feeding behavior of Epilachna paenulata (Coleoptera: Coccinellidae), a common pest of the Curcubitaceae crops. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.026

文献信息

• Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols
  作者：Ana Bellomo、Soledad Camarano、Carmen Rossini、David Gonzalez

  DOI：10.1016/j.carres.2008.09.026

  日期：2009.1

  The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-1-chiro-inositol and deoxythio-cyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequence of enzymatic and ruthenium-catalyzed dihydroxylations, and the results were studied regarding reaction conditions and co-catalyst for different derivatives. The new compounds were included in a minilibrary of deoxygenated cyclitols and evaluated for their capacity to influence the feeding behavior of Epilachna paenulata (Coleoptera: Coccinellidae), a common pest of the Curcubitaceae crops. (C) 2008 Elsevier Ltd. All rights reserved.