ethyl (1β,2α,3β)-4-methylene-2-phenyl-3-(phenylsulfonyl)cyclopentanecarboxylate | 129801-00-9

• 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: ethyl (1β,2α,3β)-4-methylene-2-phenyl-3-(phenylsulfonyl)cyclopentanecarboxylate
• 英文别名: ethyl (1S,2S,3S)-3-(benzenesulfonyl)-4-methylidene-2-phenylcyclopentane-1-carboxylate
• CAS: 129801-00-9
• 化学式: C₂₁H₂₂O₄S
• 分子量: 370.469
• InChiKey: RTYKBQNZISJRIE-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(chloromethyl)-3-(phenylsulfonyl)-1-propene 在 sodium bromide 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 ethyl (1β,2α,3β)-4-methylene-2-phenyl-3-(phenylsulfonyl)cyclopentanecarboxylate
  参考文献：
  名称：

  A new diastereoselective 3+2 annulation approach to five-membered carbocycles.

  摘要：

  DOI：

  10.1016/s0040-4039(00)94468-x

文献信息

• A General Synthesis of Methylenecyclopentanes by a Stereoselective [3 + 2] Approach
  作者：Eugene Ghera、Tamar Yechezkel、Alfred Hassner

  DOI：10.1021/jo960089k

  日期：1996.1.1

  The [3 + 2] cyclopentanation involving 3-(phenylsulfonyl)-2-(bromomethyl)-1-propene (1) and representative (E) alpha,beta-unsaturated acyclic esters and ketones has been studied. High yields and complete stereoselectivity were observed in all reactions leading to tri- or tetrasubstituted methylenecyclopentanes. The anti-diastereoselectivity in the first, Michael addition step is rationalized by a chelation-controlled transition state in which MO interactions of the two pi systems are involved. The Michael reactions of methallyl sulfone 8 with (E) enoates in the absence and presence of HMPA confirms the influence of chelation on the diastereomeric ratio of adducts. Cyclopentanations involving 1 with cyclohexenone, 2(5H)-furanone, and 5,6-dihydro-2-pyranone, respectively, were also studied with emphasis on the factors influencing the stereochemical outcome of the annulation process.