2,4-dibromo-6-isopropylphenoxyethyl bromide | 131213-27-9

• 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: 2,4-dibromo-6-isopropylphenoxyethyl bromide
• CAS: 131213-27-9
• 化学式: C₁₁H₁₃Br₃O
• 分子量: 400.936
• InChiKey: VPQTZKFOKVMANK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,4-dibromo-6-isopropylphenoxyethyl bromide 在 正丁基锂 作用下， 生成 7-异丙基-2,3-二氢苯并呋喃
  参考文献：
  名称：

  A carbon-13 NMR study of the 1:1 hydrogen bond between trifluoroacetic acid and aromatic ethers in deuteriochloroform

  摘要：

  From the measured values of the equilibrium constants and C-13 NMR shift changes for 1:1 hydrogen bonding of trifluoroacetic acid with 2-alkyl- and 2,6-dialkylanisoles and 7-alkyl-2,3-dihydrobenzofurans in deuteriochloroform, conclusions are drawn concerning the stereochemistries of the hydrogen bonded complexes. The data indicate that hydrogen bonding of the planar 2-alkylanisoles may involve rotation of the methoxy group about the Ar-OCH3 bond, the rotational angles ranging from 13-degrees (anisole) to 43-degrees (tert-butylanisole). The values of log K1 correlate roughly with the torsional potential for methoxy group rotation in anisole, recently obtained by means of quantum mechanics, and with the angle-dependent electron densities at the methoxy oxygens that have been calculated for these o-alkylanisoles. The equilibrium constants for hydrogen bonding of the 2,6-dialkylanisoles also follow the predicted order of increasing methoxy oxygen electronic charge. The results for the rotationally rigid 2,3-dihydrobenzofurans are compatible with preferential involvement of the oxygen sp2 lone electron pair in hydrogen bond formation.

  DOI：

  10.1021/jo00002a026
• 作为产物：
  描述：

  异丙苯酚 在 sodium hydroxide 、 溴 、 potassium bromide 作用下， 以 乙醇 、 水 为溶剂， 反应 7.0h， 生成 2,4-dibromo-6-isopropylphenoxyethyl bromide
  参考文献：
  名称：

  A carbon-13 NMR study of the 1:1 hydrogen bond between trifluoroacetic acid and aromatic ethers in deuteriochloroform

  摘要：

  From the measured values of the equilibrium constants and C-13 NMR shift changes for 1:1 hydrogen bonding of trifluoroacetic acid with 2-alkyl- and 2,6-dialkylanisoles and 7-alkyl-2,3-dihydrobenzofurans in deuteriochloroform, conclusions are drawn concerning the stereochemistries of the hydrogen bonded complexes. The data indicate that hydrogen bonding of the planar 2-alkylanisoles may involve rotation of the methoxy group about the Ar-OCH3 bond, the rotational angles ranging from 13-degrees (anisole) to 43-degrees (tert-butylanisole). The values of log K1 correlate roughly with the torsional potential for methoxy group rotation in anisole, recently obtained by means of quantum mechanics, and with the angle-dependent electron densities at the methoxy oxygens that have been calculated for these o-alkylanisoles. The equilibrium constants for hydrogen bonding of the 2,6-dialkylanisoles also follow the predicted order of increasing methoxy oxygen electronic charge. The results for the rotationally rigid 2,3-dihydrobenzofurans are compatible with preferential involvement of the oxygen sp2 lone electron pair in hydrogen bond formation.

  DOI：

  10.1021/jo00002a026