5,5-bis(4'-bromophenethyl)-5,6,7,8-tetrahydroisoquinoline | 167504-28-1

• 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: 5,5-bis(4'-bromophenethyl)-5,6,7,8-tetrahydroisoquinoline
• 英文别名: 5,5-bis[2-(4-bromophenyl)ethyl]-7,8-dihydro-6H-isoquinoline
• CAS: 167504-28-1
• 化学式: C₂₅H₂₅Br₂N
• 分子量: 499.288
• InChiKey: IJDNJRBTINPZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,5-bis(4'-bromophenethyl)-5,6,7,8-tetrahydroisoquinoline 在 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 168.0h， 生成 5,5-bis-(4'-bromophenethyl)-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
• 作为产物：
  描述：

  2-(4-bromophenyl)ethyl methanesulfonate 在 氢化钾 、 ferric nitrate 、 sodium iodide 作用下， 以 氨 、 丙酮 为溶剂， 反应 33.0h， 生成 5,5-bis(4'-bromophenethyl)-5,6,7,8-tetrahydroisoquinoline
  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

• 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
  作者：Graham L. Patrick

  DOI：10.1039/p19950001273

  日期：——

  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.