1-ethyl 4-methyl 2-(phenylseleno)-2-(p-toluenesulfonyl)ethane-1,2-dicarboxylate | 257613-85-7

• 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: 1-ethyl 4-methyl 2-(phenylseleno)-2-(p-toluenesulfonyl)ethane-1,2-dicarboxylate
• 英文别名: 1-O-ethyl 4-O-methyl 2-(4-methylphenyl)sulfonyl-2-phenylselanylbutanedioate
• CAS: 257613-85-7
• 化学式: C₂₀H₂₂O₆SSe
• 分子量: 469.417
• InChiKey: OLSYUNBRNWWYRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-ethyl 4-methyl 2-(phenylseleno)-2-(p-toluenesulfonyl)ethane-1,2-dicarboxylate 在 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 1-ethyl 4-methyl (Z)-2-(p-toluenesulfonyl)ethene-1,2-dicarboxylate 、 1-ethyl 4-methyl (E)-2-(p-toluenesulfonyl)ethene-1,2-dicarboxylate
  参考文献：
  名称：

  [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates:  Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes

  摘要：

  Reaction of 1-(phenylseleno)-2-(trimethylsilyl)ethene 1 and methyl or ethyl 2-p-toluene- or benzene-sulfonylacrylates 3 in the presence of SnCl4 at -78 degrees C gave sulfone-substituted cyclopropanes 4 as single stereoisomers. The structure of one of these crystalline cyclopropane products was elucidated by X-ray crystallographic analysis. The relative stereochemistry of the cyclopropane ring carbon (C-2) and selenosilylmethyl group was determined as R,R and S,S, which is consistent with previous mechanical considerations and the NOE determination. 2-Sulfinyl acrylate 2 did not undergo this cycloaddition. The difference in reactivity of the sulfoxide 2 and sulfones 3 toward 1 was explained by comparison of LUMO levels of 2-SnCl4 and 3-SnCl4 complexes and activation energies in the synclinal addition of 1 to the complexes.

  DOI：

  10.1021/jo9911591
• 作为产物：
  描述：

  4-甲基-(苯基磺酰基)乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 1-ethyl 4-methyl 2-(phenylseleno)-2-(p-toluenesulfonyl)ethane-1,2-dicarboxylate
  参考文献：
  名称：

  [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates:  Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes

  摘要：

  Reaction of 1-(phenylseleno)-2-(trimethylsilyl)ethene 1 and methyl or ethyl 2-p-toluene- or benzene-sulfonylacrylates 3 in the presence of SnCl4 at -78 degrees C gave sulfone-substituted cyclopropanes 4 as single stereoisomers. The structure of one of these crystalline cyclopropane products was elucidated by X-ray crystallographic analysis. The relative stereochemistry of the cyclopropane ring carbon (C-2) and selenosilylmethyl group was determined as R,R and S,S, which is consistent with previous mechanical considerations and the NOE determination. 2-Sulfinyl acrylate 2 did not undergo this cycloaddition. The difference in reactivity of the sulfoxide 2 and sulfones 3 toward 1 was explained by comparison of LUMO levels of 2-SnCl4 and 3-SnCl4 complexes and activation energies in the synclinal addition of 1 to the complexes.

  DOI：

  10.1021/jo9911591

文献信息

• [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates:  Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes
  作者：Shoko Yamazaki、Yuichiro Yanase、Etsuko Tanigawa、Shinichi Yamabe、Hatsue Tamura

  DOI：10.1021/jo9911591

  日期：1999.12.1

  Reaction of 1-(phenylseleno)-2-(trimethylsilyl)ethene 1 and methyl or ethyl 2-p-toluene- or benzene-sulfonylacrylates 3 in the presence of SnCl4 at -78 degrees C gave sulfone-substituted cyclopropanes 4 as single stereoisomers. The structure of one of these crystalline cyclopropane products was elucidated by X-ray crystallographic analysis. The relative stereochemistry of the cyclopropane ring carbon (C-2) and selenosilylmethyl group was determined as R,R and S,S, which is consistent with previous mechanical considerations and the NOE determination. 2-Sulfinyl acrylate 2 did not undergo this cycloaddition. The difference in reactivity of the sulfoxide 2 and sulfones 3 toward 1 was explained by comparison of LUMO levels of 2-SnCl4 and 3-SnCl4 complexes and activation energies in the synclinal addition of 1 to the complexes.