1,2,3,4-tetrahydro-4-methyl-6-bromospiro | 139010-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,3,4-tetrahydro-4-methyl-6-bromospiro
• 英文别名: 1,2,3,4-tetrahydro-6-bromo-4-methylspiro；6-bromo-4-methyl-1,2,3,4-tetrahydrospiro(quinoline-2-cyclohexane)；6-bromo-4-methylspiro[3,4-dihydro-1H-quinoline-2,1'-cyclohexane]
• CAS: 139010-21-2
• 化学式: C₁₅H₂₀BrN
• 分子量: 294.235
• InChiKey: HADYRMPIICSHIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-4-methyl-6-bromospiro 在 硫酸 、 sodium carbonate 、 potassium iodide 作用下， 以 正丁醇 为溶剂， 生成 6-bromo-N-(γ-carboxypropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane]
  参考文献：
  名称：

  Chemistry of N-functionalized spirodihydroquinolines. Unusual access to the 3-methyl-4-(2-oxo-pyrrolidinyl-1)spiro[indane-1,1′-cyclohexanes] from 1-(3-cyanopropyl)-3,4-dihydrospiro[quinoline-2,1′-cyclohexanes]

  摘要：

  The transformation of N-substituted 3,4-dihydrospiro[quinoline-2,1'-cyclohexanes] 2 and 3 has been examined in strong acid media, at elevated temperature. It was demonstrated that the N-(gamma-cyanopropyl) spirodihydroquinolines 2 in the presence of concentrated sulfuric acid or PPA underwent hydrolysis affording the gamma-aminoacids 3. The spirodihydroquinoline ring rearrangement readily produces 4-(2-oxopyrrolidinyl-1)spiro[indane-1,1'-cyclohexanes] 5 in good yields. The structures of all synthesized compounds were established by means of homonuclear and inverse-detected 2D NMR experiments. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01476-x
• 作为产物：
  描述：

  N-cyclohexylidene-p-bromoaniline 在 硫酸 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成 1,2,3,4-tetrahydro-4-methyl-6-bromospiro
  参考文献：
  名称：

  Bromine-substituted 1,2,3,4-tetrahydro-4-methylspiro[quinoline-2-cyclohexanes]

  摘要：

  DOI：

  10.1007/bf00486802

文献信息

• Synthesis and spectral data of unknown lilolidine spiro derivatives
  作者：Alirio Palma R、Javier Silva、Elena Stashenko、Jairo René Martínez、Vladimir Kouznetsov

  DOI：10.1002/jhet.5570360316

  日期：1999.5

  A new series of halo and methyl substituted spiro annulated tetrahydropyrrolo[3,2,1-ij]quinolines, analogues of lilolidine alkaloids has been prepared in a two-step route from easily accessible dihydroquinoline precursors.

  从容易获得的二氢喹啉前体分两步制备了一系列新的卤素和甲基取代的螺环化的四氢吡咯并[3,2,1- ij ]喹啉类似物。
• Unexpected and novel synthesis of spirojulolidines via intramolecular cyclization of N-carbethoxymethyl spirotetrahydroquinolines catalyzed by PPA
  作者：Alirio Palma、Claudia Carrillo、Elena Stashenko、Vladimir Kouznetsov、Alı́ Bahsas、Juan Amaro-Luis

  DOI：10.1016/s0040-4039(01)01177-7

  日期：2001.9

  A series of N-carbethoxymethyl spirotetrahydroquinolines (6) were prepared and subjected to cyclization. We show that cyclization of (6) in the presence of excess PPA results in a 50–62% yield of unexpected spirojulolidines (7).

  制备了一系列的N-乙氧甲基甲基螺四氢喹啉（6）并进行环化。我们证明了（6）在过量PPA存在下的环化反应会产生50-62％的意想不到的螺吡咯烷嘧啶核苷（7）。
• Studies directed to the synthesis of new C-5 spiroannulated julolidines
  作者：Alirio Palma、Javier Silva Agredo、Claudia Carrillo、Vladimir Kouznetsov、Elena Stashenko、Alı́ Bahsas、Juan Amaro-Luis

  DOI：10.1016/s0040-4020(02)01095-5

  日期：2002.10

  Two series of new 7,9-disubstituted spirojulolidines 8a-d and 10a-e were synthesized by acid catalyzed intramolecular cyclization of N-(3-chloropropanoyl) spirodihydroquinolines 5a-d and N-carbethoxymethyl spirodihydroquinolines 7a-e using AlCl3 and PPA, respectively. The spectroscopic analyses of intermediate compounds and the final spirojulolidines were discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of N-alkyl(acyl)-1,2,3,4-tetrahydro-4-methylspiro [quinoline-2-cyclohexanes] and their conversions
  作者：V. V. Kuznetsov、A. Pal'ma、A. �. Aliev、N. S. Prostakov、A. V. Varlamov

  DOI：10.1007/bf00531546

  日期：1993.6
• Synthesis, chemical transformations, and structure of 1,2,3,4-tetrahydrospiro(quinoline-2-cycloalkanes)
  作者：V. V. Kuznetsov、A. �. Aliev、A. R. Pal'ma、A. V. Varlamov、N. S. Prostakov

  DOI：10.1007/bf00476208

  日期：1991.7