1-(2-phenylthioethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane | 444168-94-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(2-phenylthioethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 444168-94-9
• 化学式: C₁₄H₁₈O₃S
• 分子量: 266.361
• InChiKey: ZCSJVJITVFFFOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-phenylthioethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 在 六甲基磷酰三胺 、 叔丁基锂 、 [双(三氟甲磺酰基)氨基]三甲基硅烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (1'R,3'aS,7'aS)-5-(hydroxymethyl)-5-methyl-1'-phenylsulfanylspiro[1,3-dioxane-2,3'-2,3a,5,6,7,7a-hexahydro-1H-indene]-4'-one
  参考文献：
  名称：

  Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function

  摘要：

  1,1-Dimethyl-3-(phenyldio)-propane 4 was deprotonated with t-BuLi, then converted to the corresponding organocuprate reagent which, in the presence of HMPA and TMSCl was added to a variety of enones to give the corresponding silylenol ethers 7. These were cyclised without purification upon acidic conditions to give the cyclopentannulation products 9. A similar result was obtained with the corresponding orthoester reagent 6. This cyclopentannulation sequence is applicable to a wide variety of enones except for those bearing substituents near the reacting centre. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01248-0
• 作为产物：
  描述：

  3-苯硫基丙酸 在 三氟化硼乙醚 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 37.0h， 生成 1-(2-phenylthioethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
  参考文献：
  名称：

  Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function

  摘要：

  1,1-Dimethyl-3-(phenyldio)-propane 4 was deprotonated with t-BuLi, then converted to the corresponding organocuprate reagent which, in the presence of HMPA and TMSCl was added to a variety of enones to give the corresponding silylenol ethers 7. These were cyclised without purification upon acidic conditions to give the cyclopentannulation products 9. A similar result was obtained with the corresponding orthoester reagent 6. This cyclopentannulation sequence is applicable to a wide variety of enones except for those bearing substituents near the reacting centre. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01248-0