7-p-tolyl-heptanoyl chloride | 100792-68-5

• 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: 7-p-tolyl-heptanoyl chloride
• 英文别名: 7-p-tolyl-heptanoyl chloride；7-p-Tolyl-heptanoylchlorid
• CAS: 100792-68-5
• 化学式: C₁₄H₁₉ClO
• 分子量: 238.757
• InChiKey: WOONSRDFVJPBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  7-p-tolyl-heptanoyl chloride 在 二硫化碳 、 三氯化铝 作用下， 生成 3-methyl-6,7,8,9,10,11-hexahydro-benzocyclononen-5-one
  参考文献：
  名称：

  Huisgen; Vossius, Monatshefte fur Chemie, 1957, vol. 88, p. 517,527

  摘要：

  DOI：
• 作为产物：
  描述：

  三苯基膦 在 palladium on activated charcoal 草酰氯 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 44.0h， 生成 7-p-tolyl-heptanoyl chloride
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r