ethyl 2-(phenylsulfinyl)pentanoate | 100200-74-6

• 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 2-(phenylsulfinyl)pentanoate
• 英文别名: Ethyl 2-(benzenesulfinyl)pentanoate
• CAS: 100200-74-6
• 化学式: C₁₃H₁₈O₃S
• 分子量: 254.35
• InChiKey: XPQICHOXGVXJJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(phenylsulfinyl)pentanoate 以 甲苯 为溶剂， 反应 5.0h， 生成 ethyl 2-pentenoate
  参考文献：
  名称：

  Radical Mechanism in the Elimination of 2-Arylsulfinyl Esters

  摘要：

  The mechanism of the dehydrosulfenylation of 2-arylsulfinyl esters was investigated. The reaction was found to follow a homolytic cleavage mechanism as verified by electrospray ionization tandem mass spectrometry and experimental work. Rearranged sulfoxides are obtained as byproduct during the elimination reaction.

  DOI：

  10.1021/jo300699w
• 作为产物：
  描述：

  ethyl 2-(phenylthio)pentanoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到ethyl 2-(phenylsulfinyl)pentanoate
  参考文献：
  名称：

  Radical Mechanism in the Elimination of 2-Arylsulfinyl Esters

  摘要：

  The mechanism of the dehydrosulfenylation of 2-arylsulfinyl esters was investigated. The reaction was found to follow a homolytic cleavage mechanism as verified by electrospray ionization tandem mass spectrometry and experimental work. Rearranged sulfoxides are obtained as byproduct during the elimination reaction.

  DOI：

  10.1021/jo300699w

文献信息

• An unusually facile diels-alder reaction with novel 6-alkylthio derivatives of 1,2,4-triazine
  作者：Edward C. Taylor、John E. Macor

  DOI：10.1016/s0040-4039(00)94841-x

  日期：1985.1

  Treatment of a series of 6-alkylthio-, 6-alkylsulfinyl- and 6-alkylsulfonyl-1,2,4-triazines with 1-pyrrolidinocyclopentene yields 3,4-cyclopentenopyridines. The observed rates of these cycloaddition reactions (sulfide < sulfoxide < sulfoxide) are consistent with an inverse electron-demand Diels-Alder reaction.

  用1-吡咯烷基环戊烯处理一系列6-烷硫基-，6-烷基亚磺酰基-和6-烷基磺酰基-1,2,4-三嗪，得到3,4-环戊烯吡啶。观察到的这些环加成反应的速率（硫化物<亚砜<亚砜）与电子需求逆Diels-Alder反应一致。
• MILLER, R. D.;HAESSIG, R., TETRAHEDRON LETT., 1985, 26, N 20, 2395-2398
  作者：MILLER, R. D.、HAESSIG, R.

  DOI：——

  日期：——
• Eliminative deoxygenation: A facile synthesis of α-cyano and α-carboalkoxy substituted vinyl sulfides
  作者：R.D. Miller、R. Hässig

  DOI：10.1016/s0040-4039(00)94836-6

  日期：1985.1
• Radical Mechanism in the Elimination of 2-Arylsulfinyl Esters
  作者：Antonio Latorre、Irakusne López、Victoria Ramírez、Santiago Rodríguez、Javier Izquierdo、Florenci V. González、Cristian Vicent

  DOI：10.1021/jo300699w

  日期：2012.6.1

  The mechanism of the dehydrosulfenylation of 2-arylsulfinyl esters was investigated. The reaction was found to follow a homolytic cleavage mechanism as verified by electrospray ionization tandem mass spectrometry and experimental work. Rearranged sulfoxides are obtained as byproduct during the elimination reaction.