3-pyridylmethyl p-tolyl sulfoxide | 106651-90-5

• 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: 3-pyridylmethyl p-tolyl sulfoxide
• 英文别名: 3-(Toluene-4-sulfinylmethyl)-pyridine；3-[(4-methylphenyl)sulfinylmethyl]pyridine
• CAS: 106651-90-5
• 化学式: C₁₃H₁₃NOS
• 分子量: 231.318
• InChiKey: AQCHTWNLOSWZMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-pyridylmethyl p-tolyl sulfoxide 、 碘甲烷 、 lithium diisopropyl amide 以90%的产率得到
  参考文献：
  名称：

  FURUKAWA, NAOMICHI;HOSONO, ERI;FUJIHARA, HISASHI;OGAWA, SATOSHI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 461-465

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯甲基吡啶盐酸盐 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.25h， 生成 3-pyridylmethyl p-tolyl sulfoxide
  参考文献：
  名称：

  2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives: New bronchosecretolytic agents

  摘要：

  2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives (1a-n) promote the excretion of phenol red into the mouse trachea, indicating an increased tracheobronchial secretion. Furthermore, 2-[(3-pyridinylmethyl)thio]pyrimidine (1a) (tasuldine) produces greater excretion of phenol red into the mouse trachea after systemic administration than the known bronchosecretolytic ambroxol. Compound 1a also reduces the viscosity of canine bronchial mucus. Compound 1a has been selected for clinical investigations.

  DOI：

  10.1021/jm00386a018

文献信息

• Studies on the Stereoselective Methylation of α-Sulfinyl Carbanions Generated from Three Isomeric Pyridylmethyl<i>p</i>-Tolyl Sulfoxides and Benzyl 2-Pyridyl Sulfoxide
  作者：Naomichi Furukawa、Eri Hosono、Hisashi Fujihara、Satoshi Ogawa

  DOI：10.1246/bcsj.63.461

  日期：1990.2

  A high stereoselectivity in the methylation of 2-pyridylmethyl p-tolyl sulfoxide (2a) with lithium diisopropylamide and iodomethane was observed at low temperature. The chelation of Li+ by both the nitrogen atom in the pyridine ring and the sulfinyl oxygen atom in 2a promotes the stereoselectivity as compared with isomeric sulfoxides.

  在低温下观察到 2-吡啶基甲基对甲苯基亚砜 (2a) 与二异丙基氨基锂和碘甲烷的甲基化具有高立体选择性。与异构亚砜相比，吡啶环中的氮原子和 2a 中的亚磺酰基氧原子对 Li+ 的螯合提高了立体选择性。
• FURUKAWA, NAOMICHI;HOSONO, ERI;FUJIHARA, HISASHI;OGAWA, SATOSHI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 461-465
  作者：FURUKAWA, NAOMICHI、HOSONO, ERI、FUJIHARA, HISASHI、OGAWA, SATOSHI

  DOI：——

  日期：——
• 2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives: New bronchosecretolytic agents
  作者：Helmut Schickaneder、Heidrun Engler、Istvan Szelenyi

  DOI：10.1021/jm00386a018

  日期：1987.3

  2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives (1a-n) promote the excretion of phenol red into the mouse trachea, indicating an increased tracheobronchial secretion. Furthermore, 2-[(3-pyridinylmethyl)thio]pyrimidine (1a) (tasuldine) produces greater excretion of phenol red into the mouse trachea after systemic administration than the known bronchosecretolytic ambroxol. Compound 1a also reduces the viscosity of canine bronchial mucus. Compound 1a has been selected for clinical investigations.