7,7-dimethoxy-5-(phenylthio)heptan-2-one | 444168-98-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 7,7-dimethoxy-5-(phenylthio)heptan-2-one
• 英文别名: 7,7-Dimethoxy-5-phenylsulfanylheptan-2-one
• CAS: 444168-98-3
• 化学式: C₁₅H₂₂O₃S
• 分子量: 282.404
• InChiKey: MOUBRMJAFUSJKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,7-dimethoxy-5-(phenylthio)heptan-2-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以93%的产率得到1-[3-(phenylthio)cyclopent-1-enyl]ethan-1-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-(phenylthio)propanal dimethyl acetal 在 六甲基磷酰三胺 、 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 7,7-dimethoxy-5-(phenylthio)heptan-2-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

文献信息

• Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function
  作者：Pingyu Ding、Léon Ghosez

  DOI：10.1016/s0040-4020(01)01248-0

  日期：2002.2

  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.