2-[2-(methylthio)phenyl]isoindolin-1-one | 622829-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[2-(methylthio)phenyl]isoindolin-1-one
• 英文别名: 2-(2-methylsulfanylphenyl)-3H-isoindol-1-one
• CAS: 622829-77-0
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: RYPCWNULLLVCMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-(methylthio)phenyl]isoindolin-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-[2-(methylsulfonyl)phenyl]isoindolin-1-one
  参考文献：
  名称：

  A Redox-Mediated Molecular Brake:  Dynamic NMR Study of 2-[2-(Methylthio)phenyl]isoindolin-1-one and S-Oxidized Counterparts

  摘要：

  A redox-mediated molecular brake based on the sulfide - sulfoxide redox cycle is illustrated by modulation of the rotation rate of an N-Ar "shaft" by varying the oxidation state of sulfur in 2-[2-(sulfur-substituted)phenyl]isoindolin-l-ones. N-Ar rotational barriers in methylsulfinyl (2) and methylsulfonyl (3) derivatives (13.6 kcal mol(-1)) are similar to5 kcal mol(-1) higher than sulfide 1. Rate reduction for N-Ar rotation is similar to10(4) s(-1) (280 K) upon oxidation. Correlated N-pyramidalization/N-Ar rotation reduces the effectiveness of the brake by decreasing the energy barrier to N-Ar bond rotation.

  DOI：

  10.1021/jo034613g
• 作为产物：
  描述：

  2-氨基茴香硫醚 、 邻苯二甲醛 在 溶剂黄146 作用下， 反应 0.33h， 以30%的产率得到2-[2-(methylthio)phenyl]isoindolin-1-one
  参考文献：
  名称：

  A Redox-Mediated Molecular Brake:  Dynamic NMR Study of 2-[2-(Methylthio)phenyl]isoindolin-1-one and S-Oxidized Counterparts

  摘要：

  A redox-mediated molecular brake based on the sulfide - sulfoxide redox cycle is illustrated by modulation of the rotation rate of an N-Ar "shaft" by varying the oxidation state of sulfur in 2-[2-(sulfur-substituted)phenyl]isoindolin-l-ones. N-Ar rotational barriers in methylsulfinyl (2) and methylsulfonyl (3) derivatives (13.6 kcal mol(-1)) are similar to5 kcal mol(-1) higher than sulfide 1. Rate reduction for N-Ar rotation is similar to10(4) s(-1) (280 K) upon oxidation. Correlated N-pyramidalization/N-Ar rotation reduces the effectiveness of the brake by decreasing the energy barrier to N-Ar bond rotation.

  DOI：

  10.1021/jo034613g

文献信息

• A Redox-Mediated Molecular Brake:  Dynamic NMR Study of 2-[2-(Methylthio)phenyl]isoindolin-1-one and <i>S</i>-Oxidized Counterparts
  作者：Parag V. Jog、Richard E. Brown、Dallas K. Bates

  DOI：10.1021/jo034613g

  日期：2003.10.1

  A redox-mediated molecular brake based on the sulfide - sulfoxide redox cycle is illustrated by modulation of the rotation rate of an N-Ar "shaft" by varying the oxidation state of sulfur in 2-[2-(sulfur-substituted)phenyl]isoindolin-l-ones. N-Ar rotational barriers in methylsulfinyl (2) and methylsulfonyl (3) derivatives (13.6 kcal mol(-1)) are similar to5 kcal mol(-1) higher than sulfide 1. Rate reduction for N-Ar rotation is similar to10(4) s(-1) (280 K) upon oxidation. Correlated N-pyramidalization/N-Ar rotation reduces the effectiveness of the brake by decreasing the energy barrier to N-Ar bond rotation.