methyl 2-allyl-2-hydroxycyclohexane-1-carbodithioate | 1534385-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-allyl-2-hydroxycyclohexane-1-carbodithioate
• CAS: 1534385-36-8
• 化学式: C₁₁H₁₈OS₂
• 分子量: 230.395
• InChiKey: SKHZFGZAULJEJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-allyl-2-hydroxycyclohexane-1-carbodithioate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以84%的产率得到3-methyl-1-(methylthio)-5,6,7,8-tetrahydro-3H-isothio chromene
  参考文献：
  名称：

  Regioselective dehydrative intramolecular heteroannulation of β-allyl-β-hydroxy dithioesters: facile and straightforward entry to 2H-thiopyrans

  摘要：

  beta-Allyl-beta-hydroxy dithioesters have been employed in the synthesis of hitherto unreported and synthetically demanding 2H-thiopyrans via regioselective intramolecular annulation strategy. Lewis acid BF3 center dot Et2O efficiently mediates the regioselective dehydration followed by intramolecular thioannulation at room temperature. The attractive features of this protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.020
• 作为产物：
  描述：

  S-methyl cyclohexanone-2-dicarboxylate 、 烯丙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 生成 methyl 2-allyl-2-hydroxycyclohexane-1-carbodithioate
  参考文献：
  名称：

  Regioselective dehydrative intramolecular heteroannulation of β-allyl-β-hydroxy dithioesters: facile and straightforward entry to 2H-thiopyrans

  摘要：

  beta-Allyl-beta-hydroxy dithioesters have been employed in the synthesis of hitherto unreported and synthetically demanding 2H-thiopyrans via regioselective intramolecular annulation strategy. Lewis acid BF3 center dot Et2O efficiently mediates the regioselective dehydration followed by intramolecular thioannulation at room temperature. The attractive features of this protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.020