3-[2-(4-Bromo-benzyloxy)-phenyl]-5-chloromethyl-isoxazole | 600740-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[2-(4-Bromo-benzyloxy)-phenyl]-5-chloromethyl-isoxazole
• 英文别名: 3-[2-[(4-bromophenyl)methoxy]phenyl]-5-(chloromethyl)-1,2-oxazole
• CAS: 600740-19-0
• 化学式: C₁₇H₁₃BrClNO₂
• 分子量: 378.653
• InChiKey: WWPOLSXCEBBWCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 3-[2-(4-Bromo-benzyloxy)-phenyl]-5-chloromethyl-isoxazole 在 sodium hypochlorite 作用下， 以 二氯甲烷 为溶剂， 生成 3-[2-(4-Bromo-benzyloxy)-phenyl]-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  3-(2-Benzyloxyphenyl)isoxazoles and isoxazolines: synthesis and evaluation as CFTR activators

  摘要：

  A novel class of activators for chloride conductance in the cystic fibrosis transmembrane conductance regulator (CFTR) protein has been identified. These 3-(2-benzyloxyphenyl)isoxazoles and 3-(2-benzyloxyphenyl)isoxazolines were synthesized employing the 1.3-dipolar cycloaddition of nitrile oxides with various alkene and alkyne dipolarophiles. Utilizing a fluorescence cell-based assay of halide transport, the best compounds increased CFTR-dependent chloride transport with half-maximal stimulation at 20-50 muM. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00482-7
• 作为产物：
  描述：

  2-[(4-溴苄基)氧基]苯甲醛 在 sodium hypochlorite 、 盐酸羟胺 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 生成 3-[2-(4-Bromo-benzyloxy)-phenyl]-5-chloromethyl-isoxazole
  参考文献：
  名称：

  3-(2-Benzyloxyphenyl)isoxazoles and isoxazolines: synthesis and evaluation as CFTR activators

  摘要：

  A novel class of activators for chloride conductance in the cystic fibrosis transmembrane conductance regulator (CFTR) protein has been identified. These 3-(2-benzyloxyphenyl)isoxazoles and 3-(2-benzyloxyphenyl)isoxazolines were synthesized employing the 1.3-dipolar cycloaddition of nitrile oxides with various alkene and alkyne dipolarophiles. Utilizing a fluorescence cell-based assay of halide transport, the best compounds increased CFTR-dependent chloride transport with half-maximal stimulation at 20-50 muM. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00482-7

文献信息

• 3-(2-Benzyloxyphenyl)isoxazoles and isoxazolines: synthesis and evaluation as CFTR activators
  作者：Robert E Sammelson、T Ma、Luis J.V Galietta、A.S Verkman、Mark J Kurth

  DOI：10.1016/s0960-894x(03)00482-7

  日期：2003.8

  A novel class of activators for chloride conductance in the cystic fibrosis transmembrane conductance regulator (CFTR) protein has been identified. These 3-(2-benzyloxyphenyl)isoxazoles and 3-(2-benzyloxyphenyl)isoxazolines were synthesized employing the 1.3-dipolar cycloaddition of nitrile oxides with various alkene and alkyne dipolarophiles. Utilizing a fluorescence cell-based assay of halide transport, the best compounds increased CFTR-dependent chloride transport with half-maximal stimulation at 20-50 muM. (C) 2003 Elsevier Ltd. All rights reserved.