2-(methylsulfinyl)-1-(2-quinolinyl)ethanone | 123005-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(methylsulfinyl)-1-(2-quinolinyl)ethanone
• 英文别名: 2-Methylsulfinyl-1-quinolin-2-ylethanone
• CAS: 123005-10-7
• 化学式: C₁₂H₁₁NO₂S
• 分子量: 233.291
• InChiKey: XWEWVSLMEXRORF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(methylsulfinyl)-1-(2-quinolinyl)ethanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (RS/SR)-2-(Methylsulfinyl)-1-(2-quinolyl)ethanol 、 (RR/SS)-2-(Methylsulfinyl)-1-(2-quinolyl)ethanol
  参考文献：
  名称：

  Synthesis, Configurational Assignment and Conformational Analysis of .beta.-Hydroxy Sulfoxides, Bioisosteres of Oxisuran Metabolites, and their O-Methyl Derivatives

  摘要：

  Synthesis, configurational assignment, and conformational analysis of diastereoisomers of 2-(methylsulfinyl)-1-(2-quinolyl)ethanol, 3a, 2-(methylsulfinyl)-1-(1-isoquinolyl)ethanol, 3b, 2-(methylsulfinyl)-1-(2-pyrazyl)ethanol, 3c, and their O-methyl derivatives 4a-c are reported. The configurational assignment and conformational analysis of the two diastereoisomers of beta-hydroxy sulfoxides and beta-methoxy sulfoxides have been carried out from the observed vicinal coupling constants using the molecular mechanics force field (MMX) and the Altona relationship as fundamental tools. The conformational equilibrium is explained in terms of polar and steric factors. Of significant importance was the role of intramolecular hydrogen bonding in the RS/SR isomers of beta-hydroxy sulfoxides.

  DOI：

  10.1021/jo00103a019
• 作为产物：
  描述：

  1-咪唑基-2-喹啉基甲酮 、 二甲基亚砜 在 甲基锂 作用下， 生成 2-(methylsulfinyl)-1-(2-quinolinyl)ethanone
  参考文献：
  名称：

  One-pot synthesis of .beta.-keto sulfones and .beta.-keto sulfoxides from carboxylic acids

  摘要：

  DOI：

  10.1021/jo00284a043

文献信息

• ALVAREZ, IBARRA C.;CUERVO, RODRIGUEZ R.;FERNANDEZ, MONREAL M. C.;GARCIA, +, J. ORG. CHEM., 54,(1989) N3, C. 5620-5623
  作者：ALVAREZ, IBARRA C.、CUERVO, RODRIGUEZ R.、FERNANDEZ, MONREAL M. C.、GARCIA, +

  DOI：——

  日期：——
• One-pot synthesis of .beta.-keto sulfones and .beta.-keto sulfoxides from carboxylic acids
  作者：C. Alvarez Ibarra、R. Cuervo Rodriguez、M. C. Fernandez Monreal、F. J. Garcia Navarro、J. Martin Tesorero

  DOI：10.1021/jo00284a043

  日期：1989.11
• Synthesis, Configurational Assignment and Conformational Analysis of .beta.-Hydroxy Sulfoxides, Bioisosteres of Oxisuran Metabolites, and their O-Methyl Derivatives
  作者：C. Alvarez-Ibarra、R. Cuervo-Rodriguez、M. C. Fernandez-Monreal、M. P. Ruiz

  DOI：10.1021/jo00103a019

  日期：1994.12

  Synthesis, configurational assignment, and conformational analysis of diastereoisomers of 2-(methylsulfinyl)-1-(2-quinolyl)ethanol, 3a, 2-(methylsulfinyl)-1-(1-isoquinolyl)ethanol, 3b, 2-(methylsulfinyl)-1-(2-pyrazyl)ethanol, 3c, and their O-methyl derivatives 4a-c are reported. The configurational assignment and conformational analysis of the two diastereoisomers of beta-hydroxy sulfoxides and beta-methoxy sulfoxides have been carried out from the observed vicinal coupling constants using the molecular mechanics force field (MMX) and the Altona relationship as fundamental tools. The conformational equilibrium is explained in terms of polar and steric factors. Of significant importance was the role of intramolecular hydrogen bonding in the RS/SR isomers of beta-hydroxy sulfoxides.