5-<2-(4-bromophenyl)ethyl>-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline | 167504-32-7

• 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: 5-<2-(4-bromophenyl)ethyl>-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline
• 英文别名: (+/-)-5-(4'-bromophenethyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline；5-[2-(4-bromophenyl)ethyl]-2-methyl-3,4,5,6,7,8-hexahydro-1H-isoquinoline
• CAS: 167504-32-7
• 化学式: C₁₈H₂₄BrN
• 分子量: 334.299
• InChiKey: YLNIMQFGOJOUBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-<2-(4-bromophenyl)ethyl>-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline 在 氢溴酸 作用下， 以52%的产率得到(+/-)-<4aα,4bβ,10bβ,12aβ>-9-bromo-2-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho<2,1-f>isoquinoline
  参考文献：
  名称：

  Synthesis of (±)-[4aα,4bβ,10bβ,12aβ]-9-halogeno-2-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-ƒ]isoquinolines

  摘要：

  Treatment of 5-(2-arylethyl)-1,2,3,4,5,6,7,8-octahydroisoquinolines with 48% HBr resulted in isomerisation of the double bond and subsequent cyclisation at position 6 of the octahydroisoquinoline ring system to give (+/-)-[4a alpha,4b beta,10b beta,12a beta]-9-halogeno-2-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho-[2,1-f]isoquinolines. The products obtained represent novel analogues of aza-D-homoestranes. No reaction was observed with the corresponding 5,5-disubstituted octahydroisoquinolines. An X-ray crystallographic study of compound 10 (X = Br) is described.

  DOI：

  10.1039/p19950001273
• 作为产物：
  描述：

  2-(4-bromophenyl)ethyl methanesulfonate 在 sodium tetrahydroborate 、 氢化钾 、 ferric nitrate 、 sodium iodide 作用下， 以 乙醚 、 乙醇 、 氨 、 丙酮 为溶剂， 反应 201.0h， 生成 5-<2-(4-bromophenyl)ethyl>-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline
  参考文献：
  名称：

  Synthesis of (±)-[4aα,4bβ,10bβ,12aβ]-9-halogeno-2-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-ƒ]isoquinolines

  摘要：

  Treatment of 5-(2-arylethyl)-1,2,3,4,5,6,7,8-octahydroisoquinolines with 48% HBr resulted in isomerisation of the double bond and subsequent cyclisation at position 6 of the octahydroisoquinoline ring system to give (+/-)-[4a alpha,4b beta,10b beta,12a beta]-9-halogeno-2-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho-[2,1-f]isoquinolines. The products obtained represent novel analogues of aza-D-homoestranes. No reaction was observed with the corresponding 5,5-disubstituted octahydroisoquinolines. An X-ray crystallographic study of compound 10 (X = Br) is described.

  DOI：

  10.1039/p19950001273

文献信息

• (±)-(4aα,4bβ,10bβ,12aβ)-9-Bromo-2-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinoline Formed from the Acid-Catalyzed Cyclization of 5-[2-(4-Bromophenyl)ethyl]-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline
  作者：G. L. Patrick、A. C. Willis

  DOI：10.1107/s0108270195004975

  日期：1995.9.15

  The title compound, C18H24BrN, was produced by treating 5-[2-(4-bromophenyl)ethyl]-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline with 48% hydrobromic acid. Cyclization took place between position 2 of the aromatic ring and position 6 of the octahydroisoquinoline ring, following acid-catalyzed isomerization of the double bond.