1-(benzyloxy)-2-(1-chloroethyl)benzene | 134940-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(benzyloxy)-2-(1-chloroethyl)benzene
• 英文别名: alpha-Methyl-2-(benzyloxy)benzyl chloride；1-(1-chloroethyl)-2-phenylmethoxybenzene
• CAS: 134940-25-3
• 化学式: C₁₅H₁₅ClO
• 分子量: 246.737
• InChiKey: QGQPSEJUPBOIKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)-2-(1-chloroethyl)benzene 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 1.0h， 生成 3-methyl-3H-benzofuran-2-one
  参考文献：
  名称：

  Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid

  摘要：

  A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, alpha-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-alpha-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.

  DOI：

  10.1021/jm00113a027
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基溴化铵 、 calcium chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 1-(benzyloxy)-2-(1-chloroethyl)benzene
  参考文献：
  名称：

  Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid

  摘要：

  A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, alpha-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-alpha-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.

  DOI：

  10.1021/jm00113a027

文献信息

• DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride
  作者：Qiang Wang、Jian Xu、Zhou-Qing Xu、Ji-Dan Yan

  DOI：10.1007/s11164-012-0738-z

  日期：2013.5

  N-phenylbenzimidoyl chloride has been demonstrated as an efficient chlorination reagent catalyzed by dimethyl sulfoxide (DMSO) in conversion of alcohols to corresponding chlorides. The reaction conditions were mild, and most of the substrates gave satisfactory yields. The configuration inversion of the chlorination was proved using optically active phenyl alcohols. The amount of DMSO can be as low as

  N-苯基苯甲酰氯已被证明是由二甲亚砜（DMSO）催化的高效氯化试剂，可将醇转化为相应的氯化物。反应条件温和，并且大多数底物给出令人满意的产率。使用旋光性苯醇证明了氯化的构型转化。在不降低氯化效率的情况下，DMSO的量可以低至0.001当量。提出了合理的反应机理，并通过实验证明。该反应在伯苄醇，仲苄醇和未活化的脂族醇中是立体选择性的，并且可能是化学选择性的。