2-(o-methoxyphenyl)imino-3-(o-methoxyphenyl)-thiazolidin-4-one | 931098-69-0

• 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: 2-(o-methoxyphenyl)imino-3-(o-methoxyphenyl)-thiazolidin-4-one
• CAS: 931098-69-0
• 化学式: C₁₇H₁₆N₂O₃S
• 分子量: 328.392
• InChiKey: KKOMQAZHAUIUQO-ZCXUNETKSA-N

物化性质

• 沸点：
  492.5±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(o-methoxyphenyl)imino-3-(o-methoxyphenyl)-thiazolidin-4-one 在 Chiracel AD-H 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 5.0h， 生成 5-benzylidene-2-(o-methoxyphenyl)imino-3-(o-methoxyphenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Axially Chiral 2-Arylimino-3-aryl-thiazolidine-4-one Derivatives:  Enantiomeric Separation and Determination of Racemization Barriers by Chiral HPLC

  摘要：

  Axially chiral 2-arylimino-3-aryl-thiazolidine-4-ones have been synthesized as racemic mixtures, and each mixture with the exception of 2-(o-chlorophenyl)imino-3-(o-chlorophenyl)-thiazolidine-4- one has been converted to the corresponding 5-benzylidene-2-arylimino-3-aryl-thiazolidine-4-one racemates by reaction with benzaldehyde. The thermally interconvertible enantiomers of each compound have been obtained by enantioselective HPLC separation on columns Chiralpak AD-H and Chiralcel OD-H, and the barriers to racemization have been found to be 98.1-114.1 kJ/mol. The barriers determined were compared to those of structurally related compounds to provide evidence for the stereochemistry of the aryl imino bond.

  DOI：

  10.1021/jo0625554
• 作为产物：
  描述：

  1,3-双(2-甲氧基苯基)硫脲 在 Chiracel OD-H 、 sodium acetate 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 6.0h， 生成 2-(o-methoxyphenyl)imino-3-(o-methoxyphenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Axially Chiral 2-Arylimino-3-aryl-thiazolidine-4-one Derivatives:  Enantiomeric Separation and Determination of Racemization Barriers by Chiral HPLC

  摘要：

  Axially chiral 2-arylimino-3-aryl-thiazolidine-4-ones have been synthesized as racemic mixtures, and each mixture with the exception of 2-(o-chlorophenyl)imino-3-(o-chlorophenyl)-thiazolidine-4- one has been converted to the corresponding 5-benzylidene-2-arylimino-3-aryl-thiazolidine-4-one racemates by reaction with benzaldehyde. The thermally interconvertible enantiomers of each compound have been obtained by enantioselective HPLC separation on columns Chiralpak AD-H and Chiralcel OD-H, and the barriers to racemization have been found to be 98.1-114.1 kJ/mol. The barriers determined were compared to those of structurally related compounds to provide evidence for the stereochemistry of the aryl imino bond.

  DOI：

  10.1021/jo0625554

文献信息

• Axially Chiral 2-Arylimino-3-aryl-thiazolidine-4-one Derivatives:  Enantiomeric Separation and Determination of Racemization Barriers by Chiral HPLC
  作者：Sule Erol、Ilknur Dogan

  DOI：10.1021/jo0625554

  日期：2007.3.1

  Axially chiral 2-arylimino-3-aryl-thiazolidine-4-ones have been synthesized as racemic mixtures, and each mixture with the exception of 2-(o-chlorophenyl)imino-3-(o-chlorophenyl)-thiazolidine-4- one has been converted to the corresponding 5-benzylidene-2-arylimino-3-aryl-thiazolidine-4-one racemates by reaction with benzaldehyde. The thermally interconvertible enantiomers of each compound have been obtained by enantioselective HPLC separation on columns Chiralpak AD-H and Chiralcel OD-H, and the barriers to racemization have been found to be 98.1-114.1 kJ/mol. The barriers determined were compared to those of structurally related compounds to provide evidence for the stereochemistry of the aryl imino bond.