3,3-dimethoxy-1-(3-oxocyclohexyl)-1-phenylthiopropane | 444168-95-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,3-dimethoxy-1-(3-oxocyclohexyl)-1-phenylthiopropane
• 英文别名: 3-(3,3-Dimethoxy-1-phenylsulfanylpropyl)cyclohexan-1-one
• CAS: 444168-95-0
• 化学式: C₁₇H₂₄O₃S
• 分子量: 308.442
• InChiKey: AGGBLXLHFMPKKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  3,3-dimethoxy-1-(3-oxocyclohexyl)-1-phenylthiopropane 在 水 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 trans-3-(3-oxocyclohexyl)-2-propenal
  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 3,3-dimethoxy-1-(3-oxocyclohexyl)-1-phenylthiopropane
  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.