N-benzyl-4-methoxy-N-[(Z)-1-(5-oxocyclopenten-1-yl)prop-1-enyl]benzenesulfonamide | 1616704-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-4-methoxy-N-[(Z)-1-(5-oxocyclopenten-1-yl)prop-1-enyl]benzenesulfonamide
• CAS: 1616704-37-0
• 化学式: C₂₂H₂₃NO₄S
• 分子量: 397.495
• InChiKey: KCVGHAYCIDAADL-OSSHXBFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-benzyl-4-methoxy-N-[(1S,5R)-7-methyl-4-oxo-6-bicyclo[3.2.0]hept-6-enyl]benzenesulfonamide 以 甲苯 为溶剂， 反应 32.0h， 以8%的产率得到N-benzyl-4-methoxy-N-[(Z)-1-(5-oxocyclopenten-1-yl)prop-1-enyl]benzenesulfonamide
  参考文献：
  名称：

  Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate

  摘要：

  Electrocyclic ring opening of 4,6-fused cyclobutenamides 1 under thermal conditions leads to cis,trans-cydooctadienones 2-E,E as transient intermediates, en route to 5,5-bicyclic products 3. Theoretical calculations predict that 4,5-fused cyclobutenamides should likewise undergo thermal ring opening, giving cis,trans-cydoheptadienones, but in this case conversion to 5,4-bicyclic products is thermodynamically disfavored, and these cyclobutenamides instead rearrange to vinyl cyclopentenones.

  DOI：

  10.1021/ja502252t

文献信息

• AlCl₃-Catalyzed Ring Expansion Cascades of Bicyclic Cyclobutenamides Involving Highly Strained <i>Cis</i>,<i>Trans</i>-Cycloheptadienone Intermediates
  作者：Xiao-Na Wang、Elizabeth H. Krenske、Ryne C. Johnston、K. N. Houk、Richard P. Hsung

  DOI：10.1021/jacs.5b02561

  日期：2015.4.29

  report the first experimental evidence for the generation of highly strained cis,trans-cycloheptadienones by electrocyclic ring opening of 4,5-fused cyclobutenamides. In the presence of AlCl3, the cyclobutenamides rearrange to [2.2.1]-bicyclic ketones; DFT calculations provide evidence for a mechanism involving torquoselective 4π-electrocyclic ring opening to a cis,trans-cycloheptadienone followed by

  我们报告了通过 4,5-稠合环丁烯酰胺的电环开环产生高度紧张的顺式，反式环庚二烯酮的第一个实验证据。在 AlCl3 存在下，环丁烯酰胺重排为 [2.2.1]-双环酮；DFT 计算为涉及对顺式，反式环庚二烯酮进行转矩选择性 4π-电环开环，然后进行类似纳扎罗夫的再环化和 1,2-烷基转移的机制提供了证据。类似地，4,6-稠合环丁烯酰胺通过顺式，反式-环辛二烯酮中间体经历AlCl3催化重排为[3.2.1]-双环酮。产物可以通过简单的级联反应进一步加工，得到复杂的三环和四环分子。
• Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a <i>Cis,Trans</i>-Cyclooctadienone Intermediate
  作者：Xiao-Na Wang、Elizabeth H. Krenske、Ryne C. Johnston、K. N. Houk、Richard P. Hsung

  DOI：10.1021/ja502252t

  日期：2014.7.16

  Electrocyclic ring opening of 4,6-fused cyclobutenamides 1 under thermal conditions leads to cis,trans-cydooctadienones 2-E,E as transient intermediates, en route to 5,5-bicyclic products 3. Theoretical calculations predict that 4,5-fused cyclobutenamides should likewise undergo thermal ring opening, giving cis,trans-cydoheptadienones, but in this case conversion to 5,4-bicyclic products is thermodynamically disfavored, and these cyclobutenamides instead rearrange to vinyl cyclopentenones.