benzyl 3-(phenylsulfonyl)-3-vinylcyclobutyl ether | 253601-22-8

• 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: benzyl 3-(phenylsulfonyl)-3-vinylcyclobutyl ether
• CAS: 253601-22-8
• 化学式: C₁₉H₂₀O₃S
• 分子量: 328.432
• InChiKey: MLZRVYMPXQQMTR-IZAXUBKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-乙酰基环戊酮 、 benzyl 3-(phenylsulfonyl)-3-vinylcyclobutyl ether 在 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到2-acetyl-2-(2-(3-benzyloxycyclobutylidene)ethyl)cyclopentanone
  参考文献：
  名称：

  Allylic Sulfones in Solid-Phase Synthesis:  Preparation of Cyclobutylidenes

  摘要：

  Polymer-bound allyl sulfones (cf. 9) were utilized in geminal cycloalkylations with epichlorohydrin to generate a cis-phenylsulfonylcyclobutanol derivative (cf. 11) in one step. In the final step of this solid-phase synthetic sequence, cuprate, organomolybdenum, and organopalladium reagents were screened to obtain an optimal protocol for "traceless" cleavage of cyclobutylidene products from the resin. Among these, palladium-catalyzed allylic alkylation was the most efficient. In addition, highly regioselective nucleophilic attack at the less hindered terminus of the allyl fragment (i.e., overall S(N)2' sulfinate displacement) was observed. Cyclobutylidene diversification was demonstrated by incorporating different allylic substituents, O-functionalizations, and C-nucleophiles to prepare a demonstration library of eight cyclobutylidene derivatives (i.e., derivatives of 4) in four steps and 30-38% overall yield from lithium polystyrene/divinylbenzene sulfinate.

  DOI：

  10.1021/jo990954b
• 作为产物：
  描述：

  烯丙基苯砜 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 benzyl 3-(phenylsulfonyl)-3-vinylcyclobutyl ether
  参考文献：
  名称：

  Allylic Sulfones in Solid-Phase Synthesis:  Preparation of Cyclobutylidenes

  摘要：

  Polymer-bound allyl sulfones (cf. 9) were utilized in geminal cycloalkylations with epichlorohydrin to generate a cis-phenylsulfonylcyclobutanol derivative (cf. 11) in one step. In the final step of this solid-phase synthetic sequence, cuprate, organomolybdenum, and organopalladium reagents were screened to obtain an optimal protocol for "traceless" cleavage of cyclobutylidene products from the resin. Among these, palladium-catalyzed allylic alkylation was the most efficient. In addition, highly regioselective nucleophilic attack at the less hindered terminus of the allyl fragment (i.e., overall S(N)2' sulfinate displacement) was observed. Cyclobutylidene diversification was demonstrated by incorporating different allylic substituents, O-functionalizations, and C-nucleophiles to prepare a demonstration library of eight cyclobutylidene derivatives (i.e., derivatives of 4) in four steps and 30-38% overall yield from lithium polystyrene/divinylbenzene sulfinate.

  DOI：

  10.1021/jo990954b