2-<4-(allyloxy)phenyl>ethyl bromide | 98704-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-<4-(allyloxy)phenyl>ethyl bromide
• 英文别名: 2-[4-(allyloxy)phenyl]ethyl bromide；1-(2-Bromoethyl)-4-prop-2-enoxybenzene
• CAS: 98704-51-9
• 化学式: C₁₁H₁₃BrO
• 分子量: 241.128
• InChiKey: GNNAJVCZLRYICX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对羟基苯乙醇 在 potassium carbonate 、 二溴三苯基膦 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 24.0h， 生成 2-<4-(allyloxy)phenyl>ethyl bromide
  参考文献：
  名称：

  Hybromet: a ligand for purifying opioid receptors

  摘要：

  Condensation of the Grignard reagent derive from 2-[4-(allyloxy)phenyl]ethyl bromide (4b) with 7 alpha-acetyl-6,14-endo-ethenotetrahydrothebaine (5) furnished the (R) tertiary carbinol, 7, which upon methoxymercuration followed by treatment with the KBr gave the bromomercurio compound 10 (Hybromet). The corresponding N-cyclopropylmethyl analogue, 11, was prepared also. The bromomercurio compound, 1, and the mercaptobenzothiazole derivative, 3, gave allyl phenyl ether when treated with BAL at room temperature. Similar treatment of 10 with BAL gave 7 in high yield. Binding studies using rat brain homogenates indicated that 7, 13, and 14 have moderately high affinities for mu rather than delta binding sites. Although much weaker, 10 showed preferential mu binding also. These results along with the fact that 10 reacted smoothly with sulfhydryl groups suggest that Hybromet would be a suitable ligand for use in affinity chromatography.

  DOI：

  10.1021/jm00150a032

文献信息

• Hybromet: a ligand for purifying opioid receptors
  作者：Sydney Archer、Josephine Michael、Peter Osei-Gyimah、Ahmad Seyed-Mozaffari、R. Suzanne Zukin、Rhoda Maneckjee、Eric J. Simon、Theresa L. Gioannini

  DOI：10.1021/jm00150a032

  日期：1985.12

  Condensation of the Grignard reagent derive from 2-[4-(allyloxy)phenyl]ethyl bromide (4b) with 7 alpha-acetyl-6,14-endo-ethenotetrahydrothebaine (5) furnished the (R) tertiary carbinol, 7, which upon methoxymercuration followed by treatment with the KBr gave the bromomercurio compound 10 (Hybromet). The corresponding N-cyclopropylmethyl analogue, 11, was prepared also. The bromomercurio compound, 1, and the mercaptobenzothiazole derivative, 3, gave allyl phenyl ether when treated with BAL at room temperature. Similar treatment of 10 with BAL gave 7 in high yield. Binding studies using rat brain homogenates indicated that 7, 13, and 14 have moderately high affinities for mu rather than delta binding sites. Although much weaker, 10 showed preferential mu binding also. These results along with the fact that 10 reacted smoothly with sulfhydryl groups suggest that Hybromet would be a suitable ligand for use in affinity chromatography.