(1S,2R,3R,6S)-6-(phenylthio)-2,3-isopropylidendioxycyclohex-4-en-1-ol | 885050-22-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1S,2R,3R,6S)-6-(phenylthio)-2,3-isopropylidendioxycyclohex-4-en-1-ol
• 英文别名: 4-deoxy-4-(phenylthio)conduritol F；(3aS,4S,5S,7aR)-2,2-dimethyl-5-phenylsulfanyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 885050-22-6
• 化学式: C₁₅H₁₈O₃S
• 分子量: 278.372
• InChiKey: NASQQKDLDAAJIY-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  64
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,6S)-6-(phenylthio)-2,3-isopropylidendioxycyclohex-4-en-1-ol 在 ruthenium trichloride 、 sodium periodate 、 水 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 48.5h， 生成 (1S,2R,3R,6S)-6-(phenylsulfonyl)cyclohex-4-ene-1,2,3-triol
  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
• 作为产物：
  描述：

  (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 在 偶氮二异丁腈 、 三正丁基氢锡 、 间氯过氧苯甲酸 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (1S,2R,3R,6S)-6-(phenylthio)-2,3-isopropylidendioxycyclohex-4-en-1-ol
  参考文献：
  名称：

  Catalytic thiolysis of chemoenzymatically derived vinylepoxides. Efficient synthesis of homochiral phenylthioconduritol F

  摘要：

  The chemoenzymatic synthesis of enantiomerically pure phenylthioconduritol F obtained in 44% overall yield is described. The key step of the synthesis is the Yb(III) thiolysis of a vinyl epoxide, which was studied in depth. The methodology is amenable to scale up and expandable to the preparation of other thiocyclitols. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.024

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.
• Catalytic thiolysis of chemoenzymatically derived vinylepoxides. Efficient synthesis of homochiral phenylthioconduritol F
  作者：Ana Bellomo、David Gonzalez

  DOI：10.1016/j.tetasy.2006.01.024

  日期：2006.2

  The chemoenzymatic synthesis of enantiomerically pure phenylthioconduritol F obtained in 44% overall yield is described. The key step of the synthesis is the Yb(III) thiolysis of a vinyl epoxide, which was studied in depth. The methodology is amenable to scale up and expandable to the preparation of other thiocyclitols. (c) 2006 Elsevier Ltd. All rights reserved.