methanesulfonic acid 3-(3-chlorophenyl)prop-2-ynyl ester | 227954-24-7

• 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: methanesulfonic acid 3-(3-chlorophenyl)prop-2-ynyl ester
• 英文别名: 3-(3-Chlorophenyl)prop-2-ynyl methanesulfonate
• CAS: 227954-24-7
• 化学式: C₁₀H₉ClO₃S
• 分子量: 244.699
• InChiKey: IWHSCYRHXNNVCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 3-(3-chlorophenyl)prop-2-ynyl ester 、 4-(4-azatricyclo<2.2.1.0^2,6>hept-1-yl)-1,2,5-thiadiazole-3-thiol 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 3-(4-Azatricyclo[2.2.1.02,6]heptan-1-yl)-4-[3-(3-chlorophenyl)prop-2-ynylsulfanyl]-1,2,5-thiadiazole
  参考文献：
  名称：

  1-(1,2,5-Thiadiazol-4-yl)-4-azatricyclo[2.2.1.0^2,6]heptanes as New Potent Muscarinic M₁ Agonists:  Structure−Activity Relationship for 3-Aryl-2-propyn-1-yloxy and 3-Aryl-2-propyn-1-ylthio Derivatives

  摘要：

  Two new series of 1-(1,2,5-thiadiazol-4-yl)-4-azatricyclo[2.2.1.0(2,6)]heptanes were synthesized and evaluated for their in vitro activity in cell lines transfected with either the human M-1 or M-2 receptor. 3-Phenyl-2-propyn-1-yloxy and -1-ylthio analogues substituted with halogen in the meta position showed high functional potency, efficacy, and selectivity toward the M-1 receptor subtype. A quite unique functional M-1 receptor selectivity was observed for compounds 8b, 8d, 8f, 9b, 9d, and 9f. Bioavailability studies in rats indicated an oral bioavailability of about 20-30%, with the N-oxide as the only detected metabolite.

  DOI：

  10.1021/jm9910019
• 作为产物：
  描述：

  间氯溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 methanesulfonic acid 3-(3-chlorophenyl)prop-2-ynyl ester
  参考文献：
  名称：

  1-(1,2,5-Thiadiazol-4-yl)-4-azatricyclo[2.2.1.0^2,6]heptanes as New Potent Muscarinic M₁ Agonists:  Structure−Activity Relationship for 3-Aryl-2-propyn-1-yloxy and 3-Aryl-2-propyn-1-ylthio Derivatives

  摘要：

  Two new series of 1-(1,2,5-thiadiazol-4-yl)-4-azatricyclo[2.2.1.0(2,6)]heptanes were synthesized and evaluated for their in vitro activity in cell lines transfected with either the human M-1 or M-2 receptor. 3-Phenyl-2-propyn-1-yloxy and -1-ylthio analogues substituted with halogen in the meta position showed high functional potency, efficacy, and selectivity toward the M-1 receptor subtype. A quite unique functional M-1 receptor selectivity was observed for compounds 8b, 8d, 8f, 9b, 9d, and 9f. Bioavailability studies in rats indicated an oral bioavailability of about 20-30%, with the N-oxide as the only detected metabolite.

  DOI：

  10.1021/jm9910019

文献信息

• Method for producing propargylamine compounds
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0810199A1

  公开（公告）日：1997-12-03

  A method for producing a propargylamine compound represented by the general formula (I): which comprises reacting a propargyl compound represented by the general formula (II): with an aromatic aldehyde represented by the general formula (III):         ArCHO     (III) and ammonia to obtain an imine compound represented by the general formula (IV): and hydrolyzing the resultant imine compound. It is to provide a method for producing a propargylamine compound from a propargyl compound by a simple operation without using a special facility, using ammonia as a reaction reagent, without producing a dipropatygylamine compound and a tripropargylamine compound as by-products.

  一种生产通式(I)所代表的丙炔胺化合物的方法： 其中包括将通式（II）所代表的丙炔化合物 与通式（III）代表的芳香醛反应： ArCHO (III) 和氨反应，得到通式（IV）代表的亚胺化合物： 并水解得到的亚胺化合物。本发明的目的是提供一种不使用特殊设备、以氨为反应试剂、通过简单操作从丙炔化合物制备丙炔胺化合物的方法，该方法不会产生二丙炔胺化合物和三丙炔胺化合物作为副产品。
• US5756769A
  申请人：——

  公开号：US5756769A

  公开（公告）日：1998-05-26